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

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186 Holiday homes

(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

    Certificate of Excellence

    from £92 / night

    £567 - £922 / week

    Book View

    Responds fast!
    avg. 30 minutes

    from £92 / night

    (14) Excellent 

      12

      Holiday guest house in Hambleton

      Rutland / Hambleton

      2 4 2 nights min

      • 2 bedrooms
      • sleeps 4
      • 2 nights min
      • Child friendly
      • Private garden

      from £86 / night

      £401 / week

      Book View

      Responds fast!
      avg. 3 hours 8 minutes

      from £86 / 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

          £825 - £1,581 / week

          Book View

          Responds fast!
          avg. 2 hours 56 minutes

          from £218 / night

          (8) 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

            £705 - £911 / week

            Book View

            from £132 / night

              11

              Cottage rental in Ketton

              Rutland / Ketton

              4 6 7 nights min

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

              from £68 / night

              £473 - £999 / week

              Enquire View

              from £68 / 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

                (7) 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

                  (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 £75 / night

                    £521 / week

                    Book View

                    Responds fast!
                    avg. 40 minutes

                    from £75 / night

                    (13) 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 £102 / night

                      £624 - £773 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 59 minutes

                      from £102 / 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

                        (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 20 minutes

                          from £115 / 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

                            (33) Excellent 

                            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

                              Certificate of Excellence

                              from £115 / night

                              £544 - £802 / week

                              Book View

                              from £115 / 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 £121 / night

                                £647 - £796 / week

                                Book View

                                from £121 / 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. 2 hours 56 minutes

                                  from £161 / 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 10 minutes

                                    from £90 / night

                                    (24) Excellent 

                                      31

                                      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

                                          (13) Excellent 

                                            23

                                            Holiday cottage in Belton-in-Rutland

                                            Rutland / Belton-in-Rutland

                                            4 6 3 nights min

                                            • 4 bedrooms
                                            • sleeps 6
                                            • 3 nights min
                                            • Nearest beach 160 km
                                            • Child friendly
                                            • Pet friendly

                                            from £85 / night

                                            £595 / week

                                            Enquire View

                                            from £85 / 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 0 minutes

                                              from £109 / night

                                              (16) Excellent 

                                              Certificate of Excellence

                                                27

                                                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 £103 / night

                                                £539 - £1,088 / week

                                                Book View

                                                Responds fast!
                                                avg. 1 hour 29 minutes

                                                from £103 / 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 £105 / night

                                                  £715 - £950 / week

                                                  Book View

                                                  from £105 / 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

                                                    from £98 / night

                                                    £682 - £974 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 58 minutes

                                                    from £98 / night

                                                    (1) 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

                                                        14

                                                        Holiday home in Greetham

                                                        Rutland / Greetham

                                                        2 4 min stay varies

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

                                                        from £126 / night

                                                        £756 - £916 / week

                                                        Book View

                                                        from £126 / 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

                                                          (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

                                                            Certificate of Excellence

                                                            from £184 / night

                                                            £1,283 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 27 minutes

                                                            from £184 / 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

                                                              £676 - £894 / week

                                                              Book View

                                                              from £114 / 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

                                                                from £172 / night

                                                                £997 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 3 hours 8 minutes

                                                                from £172 / 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. 2 hours 56 minutes

                                                                  from £144 / 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

                                                                    (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 / week

                                                                      Book View

                                                                      from £172 / 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

                                                                        (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

                                                                          £676 - £974 / week

                                                                          Book View

                                                                          from £114 / 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

                                                                                7

                                                                                Holiday home in Uppingham

                                                                                Rutland / Uppingham

                                                                                2 4 min stay varies

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

                                                                                from £115 / night

                                                                                £802 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 1 hour 0 minutes

                                                                                from £115 / night

                                                                                  7

                                                                                  Barnsdale holiday lodge rental

                                                                                  Oakham / Barnsdale

                                                                                  3 6 7 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • 7 nights min
                                                                                  • Child friendly

                                                                                  from £156 / night

                                                                                  £1,088 / week

                                                                                  Book View

                                                                                  from £156 / 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

                                                                                  Waterend Barn
                                                                                  Just perfect!!

                                                                                  The house is wonderful, it was spotlessly clean, everything was provided. We really enjoyed every minute in this house. The village is pittoresque, the area is quiet, the landscape beautiful. Beds were very comfortable, two bathrooms available. Linen and towels provided very exceptionally clean and fresh. A perfect stay, we fully recommend this place.see more
                                                                                  GLASTON, stylish interior, open-plan, Exton
                                                                                  Pleasantly surprised

                                                                                  We booked this last minute (couple of days before we planned to travel) and, with only a small selection of properties available in the area, figured we may have to accept a few concessions. Not so with this lodge. Set in a lovely quiet area just North of the main road traversing the Northern shore line of Rutland Water, the reservoir is a 15 walk from the site - great for a quick dog walk, or a few minutes by car. The lodge was extremely well equipped - a home from home - and very comfortable and clean. The photos on the website unfortunately make these lodges look s bit tired (in my opinion) and do not do them justice. Made with ecology in mind, they are very warm and well insulated. Being a lovely summer, the log burner was not required but with this lit, in winter, this would create a lovely cozy atmosphere in the lodge after dark. Rutland Water and neighbouring villages have a lot to offer walkers, cyclists and nature lovers - Ospreys were in the area as we visited. The lodge takes dogs which is a bonus. Thankfully, the hotel also allows dogs in its bar/restaurant and this theme is common throughout the area with many pubs and restaurants also welcoming people with their 4 legged friends. We will most definitely be back to this lovely place.see more
                                                                                  The Gallery Apartment, Oakham, Rutland
                                                                                  In Town

                                                                                  The Gallery was clean and well maintained. The location is ideal for exploring Oakham requiring only a short walk to visit the town centre, shops and the castle etc.The WiFi worked very well and the TV offered a wide variety of programmes. … see more
                                                                                  Near Rutland Water. A Pet Friendly 18th Century Cottage with a historical Past.
                                                                                  Everything you could need from a perfect dog friendly cottage

                                                                                  Primrose Hall cottage, is a cosy comfortable home from home historic holiday accommodation. Ideal for a short or long holiday break, with everything could possibly need, to totally rest and relax. The owners have gone of their way to make sure it’s well equipped.They have thought of everything. That include Comfortable beds, good heating if needed,plenty of towels,books,games a welcoming delicious bowl of fruit, bottles of milk and wine. Our dog was spoilt too by the dog biscuits left for her. With bowls and towels for her if needed.The pretty village has a little well stocked shop and dog friendly pub all within walking distance. And others not too far away. There are plenty of lovely walks in the beautiful surrounding area. We especially fell in love with the Rutland Lakes. So much to do if you enjoy watersports, bike rides or just amazing scenery and walks around the waters. We would definitely like to stay again and have already talked our friends into making a future booking.see more
                                                                                  Character spacious High Street apartment in the heart of historic Uppingham
                                                                                  Lovely Apartment

                                                                                  Dave and Sue are delightful hosts. The flat is very clean, comfortable and stylish. Fantastic location for amenities of Uppingham. We thoroughly enjoyed our stay and would recommend the accommodation. … see more
                                                                                  Garden Apartment, Manton Lodge
                                                                                  A charming oasis with delightful views, gardens and a warm welcome.

                                                                                  A great location with easy access to Rutland Water’s walking and cycling circuit. Plenty of walking other routes. Central to Oakham & Uppingham (3 miles) and Stamford 20 minutes by car. Small villages like Brooke with a glorious church that featured in a film adaptation of Pride & Prejudice. The apartment cosy & charming. We stayed for 4 weeks Oct / Nov. The central heating was good with plenty of hot water, the layout was good with adequate cooking facilities and storage spaces though no freezer. Bedroom was perfect to wake to views of the countryside in a super king size bed and a good size bathroom. It was quiet, though I’m not sure if that had anything to do with the upstairs apartment being vacant. Reminds us so much of the Cotswolds with the honey colour stonework, weather excellent. This location and apartment filled all our requirements it was ideal.see more
                                                                                  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

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