Cottages in Rutland and Self catering accommodation - Holiday Lettings - Holiday Rentals Rutland

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189 Holiday homes

(15) Excellent 

    12

    Holiday guest house in Hambleton

    Rutland / Hambleton

    2 4 2 nights min

    • 2 bedrooms
    • sleeps 4
    • 2 nights min
    • Nearest beach 3 km
    • Child friendly
    • Private garden

    from £98 / night

    £401 / week

    Book View

    Responds fast!
    avg. 1 hour 28 minutes

    from £98 / night

    (40) Excellent 

    Certificate of Excellence

      21

      Cottage accommodation in Empingham

      Rutland / Empingham

      2 4 3 nights min

      • 2 bedrooms
      • sleeps 4
      • 3 nights min
      • Beach / lakeside relaxation
      • Child friendly
      • Pet friendly
      “Comfortable and Cosy Cottage in a lovely location” My wife and I stayed here for 4 nights on a cycling/walking visit to Rutland. The cottage was very clean and comfortable and superbly equipped with everything you could need plus nice touches such as wine, fruit, coffee tea and milk to get you started. The owner was very accommodating and helpful and was happy to squeeze us in at short notice. The cottage is located in a lovely village close by Rutland Water and was ideal for us as it was just a short hop on our bikes to view and enjoy this picturesque area. With the towns of Stamford and Oakham closeby it is in an ideal location to explore this delightful part of the country.

      Certificate of Excellence

      from £92 / night

      £624 - £922 / week

      Book View

      Responds fast!
      avg. 27 minutes

      from £92 / night

      (9) Excellent 

        18

        Holiday home in Uppingham

        Rutland / Uppingham

        3 6 3 nights min

        • 3 bedrooms
        • sleeps 6
        • 3 nights min
        • Child friendly
        • Pet friendly
        • Private garden

        from £132 / night

        £750 - £911 / week

        Book View

        from £132 / night

        (10) Excellent 

        Certificate of Excellence

          11

          Holiday cottage in Empingham

          Rutland / Empingham

          2 6 min stay varies

          • 2 bedrooms
          • sleeps 6
          • min stay varies
          • Child friendly
          • Private garden

          Certificate of Excellence

          from £115 / night

          £802 - £1,283 / week

          Book View

          Responds fast!
          avg. 2 hours 16 minutes

          from £115 / night

          (8) Excellent 

          Certificate of Excellence

            19

            Greetham holiday cottage rental

            Rutland / Greetham

            2 6 min stay varies

            • 2 bedrooms
            • sleeps 6
            • min stay varies
            • Child friendly
            • Pet friendly
            • Private garden

            Certificate of Excellence

            from £144 / night

            £831 - £1,214 / week

            Book View

            Responds fast!
            avg. 1 hour 30 minutes

            from £144 / night

              22

              Cottage rental in Ketton

              Rutland / Ketton

              4 6 7 nights min

              • 4 bedrooms
              • sleeps 6
              • 7 nights min
              • Child friendly
              • Pet friendly

              from £74 / night

              £515 - £1,041 / week

              Enquire View

              from £74 / night

              (4) Excellent 

                13

                Holiday lodge in Exton

                Rutland / Exton

                3 8 3 nights min

                • 3 bedrooms
                • sleeps 8
                • 3 nights min
                • Child friendly
                • Pet friendly

                from £201 / night

                £1,144 - £2,170 / week

                Book View

                from £201 / night

                (5) Excellent 

                Certificate of Excellence

                  9

                  Holiday apartment in Greetham

                  Rutland / Greetham

                  1 4 min stay varies

                  • 1 bedroom
                  • sleeps 4
                  • min stay varies
                  • Child friendly
                  • Pet friendly
                  • Private garden

                  Certificate of Excellence

                  from £115 / night

                  £682 - £985 / week

                  Book View

                  Responds fast!
                  avg. 1 hour 30 minutes

                  from £115 / night

                  (25) Very Good 

                    23

                    Holiday home accommodation

                    Rutland / Cottesmore

                    5 9 min stay varies

                    • 5 bedrooms
                    • sleeps 9
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Nearest beach 4 km
                    • Child friendly

                    from £218 / night

                    £876 - £1,581 / week

                    Book View

                    Responds fast!
                    avg. 1 hour 4 minutes

                    from £218 / night

                    (15) Excellent 

                    Certificate of Excellence

                      15

                      Apartment rental in Oakham

                      Rutland / Oakham

                      2 4 min stay varies

                      • 2 bedrooms
                      • sleeps 4
                      • min stay varies
                      • Child friendly
                      • Car not necessary
                      • Private garden

                      Certificate of Excellence

                      from £113 / night

                      £624 - £773 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 3 minutes

                      from £113 / night

                      (34) Very Good 

                      Certificate of Excellence

                        18

                        Holiday cottage in Wakerley

                        Rutland / Wakerley

                        3 8 2 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 2 nights min
                        • Child friendly
                        • Ask about pets
                        • Private garden
                        “Brilliant get-away” Absolutely amazing time away from hectic city life. The property was formerly a railway station so it is quite special when you think of the history behind the layout of the house, e.g. the original station stairs and entrance doors. Well proportioned, with spacious living room featuring three 2/3 person sofas (two of which are double sofa beds), and modern TV & DVD player. The kitchen contains everything you could possibly need for your time away, including a microwave, and a breakfast table for 6. All three bedrooms (two are upstairs and the other is downstairs) are large doubles, all comfortably hosting double beds as well as fitted wardrobes, still with plenty of floor space to spare (we were able to easily place two travel cots in the master suite, and still have quite a lot of room to move around). There are two bathrooms: downstairs there is a wet room with power shower, and upstairs there is a bath tub and shower cubicle - both were practical and clean, with very high water pressure. The boiler was also very good, we had no problems with the water getting cold, especially in the mornings when everyone had a shower (and there were 8 of us). The owners live next door, and were incredibly friendly and accommodating. Overall I would definitely recommend this cottage to others who may be interested, and having been on many other cottage breaks - I can definitely say that this was by far one of the better ones we've been to, both in terms of facilities, picturesque location (with views of fields and sheep from every angle), and value for money.

                        Certificate of Excellence

                        from £115 / night

                        £544 - £802 / week

                        Book View

                        from £115 / night

                        (34) Excellent 

                        Certificate of Excellence

                          36

                          Holiday converted chapel in Wing

                          Oakham / Wing

                          2 4 min stay varies

                          • 2 bedrooms
                          • sleeps 4
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Nearest beach 5 km

                          Certificate of Excellence

                          from £79 / night

                          £553 / week

                          Book View

                          Responds fast!
                          avg. 40 minutes

                          from £79 / night

                          (2) Excellent 

                            18

                            Holiday home rental

                            Rutland / Oakham

                            4 8 2 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 2 nights min
                            • Child friendly

                            from £184 / night

                            £1,283 / week

                            Book View

                            Responds fast!
                            avg. 51 minutes

                            from £184 / night

                            (12) Very Good 

                              8

                              North Luffenham holiday home rental

                              Rutland / North Luffenham

                              3 7 min stay varies

                              • 3 bedrooms
                              • sleeps 7
                              • min stay varies
                              • Nearest beach 5 km
                              • Child friendly
                              • Pet friendly

                              from £161 / night

                              £567 - £659 / week

                              Book View

                              Responds fast!
                              avg. 1 hour 4 minutes

                              from £161 / night

                              (6) Very Good 

                                14

                                Cottage rental in Uppingham

                                Rutland / Uppingham

                                3 5 min stay varies

                                • 3 bedrooms
                                • sleeps 5
                                • min stay varies
                                • Child friendly
                                • Car not necessary
                                • Pet friendly

                                from £138 / night

                                £682 - £796 / week

                                Book View

                                from £138 / night

                                (29) Excellent 

                                  24

                                  Edith Weston holiday cottage rental

                                  Rutland / Edith Weston

                                  2 4 3 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 3 nights min
                                  • Nearest beach 1 km
                                  • Suitable for children age 5+
                                  • Pet friendly

                                  from £100 / night

                                  £475 - £675 / week

                                  Enquire View

                                  from £100 / night

                                  (46) Very Good 

                                    24

                                    Stamford holiday cottage rental

                                    Rutland / Stamford

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Child friendly
                                    • Private garden
                                    “Relaxing” Having stayed at Two Chapel Lane with a friend in May, I would certainly make a return trip. The cottage itself is a very restful place with lovely, quality decor and very good facilities - I particularly liked the varied range of DVD's on offer and the real fire. It's proximity to Stamford and Burghley House was also very handy. Communication with the owner of the cottage was always friendly and helpful - I would thoroughly recommend staying at Two Chapel Lane and hope to do so again.

                                    from £98 / night

                                    £682 - £974 / week

                                    Book View

                                    Responds fast!
                                    avg. 1 hour 2 minutes

                                    from £98 / night

                                    (15) Excellent 

                                      28

                                      Holiday apartment in Uppingham

                                      Rutland / Uppingham

                                      3 5 2 nights min

                                      • 3 bedrooms
                                      • sleeps 5
                                      • 2 nights min
                                      • Child friendly
                                      • Car not necessary

                                      from £109 / night

                                      £573 - £813 / week

                                      Book View

                                      Responds fast!
                                      avg. 1 hour 3 minutes

                                      from £109 / night

                                      (17) Excellent 

                                      Certificate of Excellence

                                        37

                                        Holiday home in Stretton

                                        Rutland / Stretton

                                        3 6 3 nights min

                                        • 3 bedrooms
                                        • sleeps 6
                                        • 3 nights min
                                        • Child friendly
                                        • Pet friendly
                                        • Private garden

                                        Certificate of Excellence

                                        from £115 / night

                                        £539 - £1,088 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 41 minutes

                                        from £115 / night

                                        (25) Excellent 

                                          30

                                          Uppingham holiday home rental

                                          Rutland / Uppingham

                                          5 14 2 nights min

                                          • 5 bedrooms
                                          • sleeps 14
                                          • 2 nights min
                                          • Swimming pool
                                          • Pet friendly
                                          • Private garden

                                          from £1,031 / night

                                          £6,183 / week

                                          Book View

                                          from £1,031 / night

                                          (1) Excellent 

                                            21

                                            Holiday home in Oakham

                                            Rutland / Oakham

                                            4 6 2 nights min

                                            • 4 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Child friendly
                                            • Car not necessary

                                            from £138 / night

                                            £962 - £1,123 / week

                                            Book View

                                            Responds fast!
                                            avg. 40 minutes

                                            from £138 / night

                                            (5) Excellent 

                                              15

                                              Holiday apartment in Uppingham

                                              Rutland / Uppingham

                                              2 4 1 night min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 1 night min
                                              • Child friendly

                                              from £115 / night

                                              £561 - £642 / week

                                              Book View

                                              from £115 / night

                                              (3) Excellent 

                                                20

                                                B&b rental in Barnsdale

                                                Oakham / Barnsdale

                                                1 2 2 nights min

                                                • 1 bedroom
                                                • sleeps 2
                                                • 2 nights min
                                                • Beach / lakeside relaxation

                                                from £90 / night

                                                £642 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 1 minutes

                                                from £90 / night

                                                (14) Excellent 

                                                  18

                                                  Holiday cottage in Market Overton

                                                  Rutland / Market Overton

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Child friendly
                                                  • Private garden

                                                  from £115 / night

                                                  £715 - £950 / week

                                                  Book View

                                                  from £115 / night

                                                  (2) Excellent 

                                                    12

                                                    Holiday log cabin in Oakham

                                                    Rutland / Oakham

                                                    2 4 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Child friendly

                                                    from £109 / night

                                                    £602 - £1,031 / week

                                                    Book View

                                                    from £109 / night

                                                    (18) Excellent 

                                                    Certificate of Excellence

                                                      17

                                                      Holiday cottage in Cottesmore

                                                      Rutland / Cottesmore

                                                      4 10 3 nights min

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • 3 nights min
                                                      • Child friendly
                                                      • Pet friendly
                                                      • Private garden
                                                      “Lovely accommodation to a get together for new year” This property is immaculate. We arrived to fresh bread,eggs and milk and not forgetting The home baked mince pies. The beds were comfortable the showers were powerful. Very spacious in all the rooms. The garden is a fabulous size unfortunately we didn't make much use of it due to it being December and there was snow there on our arrival. There is a shop over the road and a chip shop within walking distance. We went to the Sun inn for Sunday lunch.... beautiful home cooked quality food. The best roast I have had in a while and very reasonably priced. The village itself is lovely and quiet with beautiful properties to have a nosy around. Would defintley return here. Thank you Katie.

                                                      Certificate of Excellence

                                                      from £184 / night

                                                      £1,283 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 6 minutes

                                                      from £184 / night

                                                      (42) Very Good 

                                                        29

                                                        Holiday cottage in Hambleton

                                                        Rutland / Hambleton

                                                        3 6 3 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 3 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 4 km
                                                        • Child friendly
                                                        “Excellent facilities, delightful and charming old cottage with all the mod cons to make you comfortable.” Sharon (Owner) has taken thought and care with the decor of her beautiful cottage to maintain its character and charm but also ensured it is clean and provides all the fascitiies to help you make the most of your stay. Lovely and well equipped kitchen. Having a dishwasher and washing machine is very helpful when you're away from home. Two of the bedrooms have a kingsize/double bed and the third a single bed and ideal for a child with books and it's cheerful decor. There are plenty of extras in the kitchen, not always provided in self catering, such as dishwasher tablets, washing up liquid, salt pepper, tea coffee, herbs, spices etc. I always take my own anyway when staying away as you cannot expect that all places will have so much available but it's worth sending Sharon an email to ask about anything you're not sure of to about bringing as she always replies promptly. Upstairs bathroom has a deep bath which was very comfortable it also has an overhead shower but we did not use that. Hambleton itself is lovely and quiet and very easy distance of Rutland Water which is great to cycle, walk or run round. The bed was much softer than we are used to but very comfortable and we slept well. Heating and hot water controls, easy to understand and use. Would recommend this to friends and family and happy to stay here again if we were visiting this area.

                                                        from £172 / night

                                                        £916 - £1,088 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 1 hour 28 minutes

                                                        from £172 / night

                                                        (23) Excellent 

                                                          22

                                                          Holiday cottage letting

                                                          Rutland / Oakham

                                                          2 4 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • min stay varies
                                                          • Private garden

                                                          from £114 / night

                                                          £619 - £1,065 / week

                                                          Book View

                                                          from £114 / night

                                                          (17) Very Good 

                                                          Certificate of Excellence

                                                            22

                                                            Holiday farmhouse in Manton

                                                            Oakham / Manton

                                                            1 2 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Child friendly
                                                            • Car not necessary

                                                            Certificate of Excellence

                                                            from £103 / night

                                                            £516 - £642 / week

                                                            Book View

                                                            from £103 / night

                                                            (4) Excellent 

                                                              15

                                                              Holiday barn rental

                                                              Rutland / Uffington

                                                              2 7 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 7
                                                              • min stay varies
                                                              • Child friendly

                                                              from £172 / night

                                                              £859 - £2,319 / week

                                                              Book View

                                                              from £172 / night

                                                                13

                                                                Holiday home in Greetham

                                                                Rutland / Greetham

                                                                2 4 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Child friendly
                                                                • Pet friendly
                                                                • Private garden

                                                                from £123 / night

                                                                £858 / week

                                                                Book View

                                                                from £123 / night

                                                                (2) Excellent 

                                                                  8

                                                                  Oakham holiday apartment rental

                                                                  Rutland / Oakham

                                                                  1 2 2 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 2 nights min
                                                                  • Child friendly

                                                                  from £81 / night

                                                                  £516 / week

                                                                  Book View

                                                                  from £81 / night

                                                                  (14) Very Good 

                                                                    8

                                                                    Holiday cottage letting

                                                                    Rutland / Wakerley

                                                                    1 4 min stay varies

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Child friendly
                                                                    • Pet friendly
                                                                    • Private garden

                                                                    from £144 / night

                                                                    £487 - £567 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 1 hour 4 minutes

                                                                    from £144 / night

                                                                    (18) Excellent 

                                                                      29

                                                                      Holiday cottage in Uppingham

                                                                      Rutland / Uppingham

                                                                      3 5 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 5
                                                                      • min stay varies
                                                                      • Private garden

                                                                      from £114 / night

                                                                      £619 - £1,145 / week

                                                                      Book View

                                                                      from £114 / night

                                                                        12

                                                                        Holiday log cabin letting

                                                                        Rutland / Oakham

                                                                        1 2 min stay varies

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • min stay varies

                                                                        from £142 / night

                                                                        £716 - £1,157 / week

                                                                        Book View

                                                                        from £142 / night

                                                                        (4) Excellent 

                                                                          25

                                                                          Holiday apartment in Manton

                                                                          Oakham / Manton

                                                                          1 3 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 3
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Child friendly
                                                                          • Ask about pets

                                                                          from £92 / night

                                                                          £458 - £596 / week

                                                                          Book View

                                                                          from £92 / night

                                                                          (55) Excellent 

                                                                            47

                                                                            Holiday yurt rental

                                                                            Rutland / Greetham

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £123 / night

                                                                            £1,025 / week

                                                                            Book View

                                                                            from £123 / night

                                                                            (3) Very Good 

                                                                              12

                                                                              Barn rental in Whitwell

                                                                              Rutland / Whitwell

                                                                              1 3 min stay varies

                                                                              • 1 bedroom
                                                                              • sleeps 3
                                                                              • min stay varies
                                                                              • Child friendly

                                                                              from £75 / night

                                                                              £521 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 2 hours 51 minutes

                                                                              from £75 / night

                                                                              (1) Excellent 

                                                                                12

                                                                                Holiday log cabin in Oakham

                                                                                Rutland / Oakham

                                                                                1 2 min stay varies

                                                                                • 1 bedroom
                                                                                • sleeps 2
                                                                                • min stay varies
                                                                                • Beach / lakeside relaxation
                                                                                • Nearest beach 115 km
                                                                                • Private garden

                                                                                from £150 / night

                                                                                £802 - £1,203 / week

                                                                                Book View

                                                                                from £150 / night

                                                                                  12

                                                                                  Log cabin rental in Oakham

                                                                                  Rutland / Oakham

                                                                                  1 2 min stay varies

                                                                                  • 1 bedroom
                                                                                  • sleeps 2
                                                                                  • min stay varies
                                                                                  • Beach / lakeside relaxation

                                                                                  from £150 / night

                                                                                  £802 - £1,203 / week

                                                                                  Book View

                                                                                  from £150 / night

                                                                                  Why Rutland?

                                                                                  The smallest county in England, this East Midlands delight is predominantly rural, and therefore incredibly scenic. With the enormous Rutland Water lake in the centre of the county, and plenty of activities on offer, isn’t it time you booked your next holiday rental in Rutland?

                                                                                  About Rutland

                                                                                  But there's lots of excitement to be had, both on and off the lake, and some incredible routes for walking, cycling, or just generally exploring.

                                                                                  What to Do

                                                                                  Uncover local history at the Rutland County Museum, and get a feel for what it would be like to live in such a rural area. Oakham Castle is a charming place to look around, with an unusual horseshoe collection that's well worth checking out.

                                                                                  Get out on the lake. Whether you prefer sailing or fishing, it's a beautiful place to spend some time. Or head for Aqua Park Rutland, an adrenaline-packed inflatable obstacle experience on the water that the adventurous will love.

                                                                                  Top Rutland Travel Tips

                                                                                  To enjoy some of the best of the rural English countryside, be sure to book your next holiday rental in Rutland today.

                                                                                  Top Destination reviews

                                                                                  The Old Post Office, Rutland water
                                                                                  Beautiful House

                                                                                  Beautiful house in a beautiful location. Really can’t fault this property. The owner is also very helpful and responds quickly. Highly recommend the Finches Arms pub that is opposite the house. The food was amazing. … see more
                                                                                  Self Catering Holiday Cottage
                                                                                  Excellent accommodation

                                                                                  Everything was perfect, the owners have gone out of their way to make it an amazing place to stay. Thank you … see more
                                                                                  Rutland view
                                                                                  Great place

                                                                                  We are five middle aged men who spend a long weekend away in January every year, and this year we decided to go to Oakham and chose Rutland View as our base for the weekend, and we're so glad we did. From the start of the booking process through to leaving on the Monday morning everything went smoothly. Communication was great and provided all of the information that we needed when we needed it and the house was spotlessly clean, comfortable and very well equipped. A great place and really well positioned for exploring not only Oakham, but the surrounding area.see more
                                                                                  Barrowden and Wakerley Station
                                                                                  Quirky converted station for lovely midweek stay

                                                                                  We really enjoyed our stay in this converted station. The large rooms and high ceilings were great with a tall family. Lots of parking, private gardens good for our small children. We brought our own travel cot - plenty of room for this in any bedroom. Huge staircase was fun. Nice and warm. Good location to explore the area and for us, to break a journey south. The owner was really helpful and quick to respond to queries - thank you for a super stay.see more
                                                                                  The Corner House, Uppingham, Rutland.
                                                                                  Perfect stay

                                                                                  We visited the area for a family wedding and this accommodation provided everything we needed. Everything was clean, spacious and as discribed. A nice little pub opposite (no noise from pub) the locals were very friendly and we would definitely stay again. … see more
                                                                                  The Annex in front of the lake
                                                                                  Hambleton sunshine

                                                                                  Just had a lovely weekend in this glorious village which provided splendid weather. The accommodation met our sightseeing needs and was warm and comfortable. Sharon is a great help about local good eating places as well as providing support on site. Thanks! … see more

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