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

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212 Holiday homes

(2) Excellent 

    18

    Holiday home rental

    Rutland / Oakham

    4 8 2 nights min

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

    from £144 / night

    £1,002 / week

    Book View

    Responds fast!
    avg. 51 minutes

    from £144 / 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 £102 / night

      £624 - £773 / week

      Book View

      Responds fast!
      avg. 3 hours 3 minutes

      from £102 / 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. 39 minutes

        from £79 / 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 32 minutes

          from £90 / 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

            (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

              (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

                (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

                  (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

                      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

                          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

                            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

                            (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

                                17

                                Cottage rental in Manton

                                Oakham / Manton

                                2 4 7 nights min

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

                                from £78 / night

                                £546 - £959 / week

                                Enquire View

                                from £78 / night

                                  6

                                  Braunston-in-Rutland holiday b&b rental

                                  Oakham / Braunston-in-Rutland

                                  1 2 1 night min

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

                                  from £92 / night

                                  £642 / week

                                  Book View

                                  from £92 / night

                                    6

                                    Braunston-in-Rutland holiday b&b rental

                                    Oakham / Braunston-in-Rutland

                                    1 2 1 night min

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

                                    from £92 / night

                                    £642 / week

                                    Book View

                                    from £92 / night

                                      6

                                      Holiday b&b in Braunston-in-Rutland

                                      Oakham / Braunston-in-Rutland

                                      1 2 1 night min

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

                                      from £92 / night

                                      £642 / week

                                      Book View

                                      from £92 / night

                                        6

                                        Braunston-in-Rutland holiday b&b rental

                                        Oakham / Braunston-in-Rutland

                                        1 1 1 night min

                                        • 1 bedroom
                                        • sleeps 1
                                        • 1 night min
                                        • Child friendly

                                        from £63 / night

                                        £441 / week

                                        Book View

                                        from £63 / night

                                          6

                                          Braunston-in-Rutland holiday b&b rental

                                          Oakham / Braunston-in-Rutland

                                          1 2 1 night min

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

                                          from £92 / night

                                          £642 / week

                                          Book View

                                          from £92 / night

                                            26

                                            Holiday cottage in Barnsdale

                                            Oakham / Barnsdale

                                            3 6 3 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 3 nights min
                                            • Pet friendly

                                            from £154 / night

                                            £461 - £1,550 / week

                                            Enquire View

                                            from £154 / night

                                              23

                                              Cottage rental in Barnsdale with golf nearby

                                              Oakham / Barnsdale

                                              2 4 3 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 3 nights min
                                              • Pet friendly

                                              from £132 / night

                                              £395 - £1,203 / week

                                              Enquire View

                                              from £132 / night

                                                23

                                                Holiday cottage with golf nearby in Barnsdale

                                                Oakham / Barnsdale

                                                2 4 3 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 3 nights min
                                                • Child friendly
                                                • Pet friendly

                                                from £132 / night

                                                £395 - £1,203 / week

                                                Enquire View

                                                from £132 / night

                                                (1) Excellent 

                                                  18

                                                  Barnsdale holiday cottage rental

                                                  Oakham / Barnsdale

                                                  2 4 3 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 3 nights min
                                                  • Pet friendly

                                                  from £132 / night

                                                  £395 - £1,203 / week

                                                  Enquire View

                                                  from £132 / night

                                                    28

                                                    Barnsdale holiday cottage rental

                                                    Oakham / Barnsdale

                                                    3 6 3 nights min

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

                                                    from £142 / night

                                                    £424 - £1,401 / week

                                                    Enquire View

                                                    from £142 / night

                                                      22

                                                      Holiday cottage with golf nearby in Barnsdale

                                                      Oakham / Barnsdale

                                                      3 6 3 nights min

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

                                                      from £154 / night

                                                      £461 - £1,550 / week

                                                      Enquire View

                                                      from £154 / night

                                                        25

                                                        Holiday cottage in Barnsdale

                                                        Oakham / Barnsdale

                                                        2 4 3 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 3 nights min
                                                        • Pet friendly

                                                        from £132 / night

                                                        £395 - £1,203 / week

                                                        Enquire View

                                                        from £132 / night

                                                          21

                                                          Cottage letting in Barnsdale with golf nearby

                                                          Oakham / Barnsdale

                                                          3 6 3 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 3 nights min
                                                          • Pet friendly

                                                          from £154 / night

                                                          £461 - £1,550 / week

                                                          Enquire View

                                                          from £154 / night

                                                          (1)  

                                                            23

                                                            Barnsdale holiday cottage rental

                                                            Oakham / Barnsdale

                                                            3 6 3 nights min

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

                                                            from £154 / night

                                                            £461 - £1,550 / week

                                                            Enquire View

                                                            from £154 / night

                                                              21

                                                              Holiday cottage in Barnsdale

                                                              Oakham / Barnsdale

                                                              2 4 3 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 3 nights min
                                                              • Child friendly
                                                              • Pet friendly

                                                              from £132 / night

                                                              £395 - £1,203 / week

                                                              Enquire View

                                                              from £132 / night

                                                                19

                                                                Cottage rental in Barnsdale

                                                                Oakham / Barnsdale

                                                                2 4 3 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 3 nights min
                                                                • Child friendly
                                                                • Pet friendly

                                                                from £132 / night

                                                                £395 - £1,203 / week

                                                                Enquire View

                                                                from £132 / night

                                                                  23

                                                                  Holiday home in Braunston-in-Rutland

                                                                  Oakham / Braunston-in-Rutland

                                                                  2 4 3 nights min

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

                                                                  from £78 / night

                                                                  £267 - £812 / week

                                                                  Enquire View

                                                                  from £78 / night

                                                                  (8) Excellent 

                                                                  Certificate of Excellence

                                                                    18

                                                                    Holiday home rental

                                                                    Rutland / Oakham

                                                                    3 6 3 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • 3 nights min
                                                                    • Child friendly
                                                                    • Car not necessary
                                                                    • Pet friendly

                                                                    Certificate of Excellence

                                                                    from £92 / night

                                                                    £642 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 1 hour 38 minutes

                                                                    from £92 / night

                                                                      31

                                                                      Holiday cottage with golf nearby in Barnsdale

                                                                      Oakham / Barnsdale

                                                                      3 6 3 nights min

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

                                                                      from £154 / night

                                                                      £461 - £1,550 / week

                                                                      Enquire View

                                                                      from £154 / night

                                                                      Great rentals within 20 miles that match your search

                                                                      Distance approx 2.33 miles from Oakham Show on Map

                                                                      (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. 2 hours 39 minutes

                                                                        from £86 / night

                                                                        Distance approx 15.99 miles from Oakham

                                                                        (4) Excellent 

                                                                          21

                                                                          Holiday lodge in Market Deeping

                                                                          Lincolnshire / Market Deeping

                                                                          1 2 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • min stay varies
                                                                          • Child friendly

                                                                          from £155 / night

                                                                          £745 / week

                                                                          Book View

                                                                          from £155 / night

                                                                          Distance approx 10.63 miles from Oakham Show on Map

                                                                          (5) Excellent 

                                                                          Certificate of Excellence

                                                                            21

                                                                            Stamford holiday farmhouse rental

                                                                            Lincolnshire / Stamford

                                                                            6 14 min stay varies

                                                                            • 6 bedrooms
                                                                            • sleeps 14
                                                                            • min stay varies
                                                                            • Child friendly
                                                                            • Car not necessary
                                                                            • Pet friendly

                                                                            Certificate of Excellence

                                                                            from £956 / night

                                                                            £6,693 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 1 hour 21 minutes

                                                                            from £956 / night

                                                                            Distance approx 7.71 miles from Oakham Show on Map

                                                                              12

                                                                              Log cabin rental in Stamford

                                                                              Lincolnshire / Stamford

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Child friendly

                                                                              from £109 / night

                                                                              £602 - £1,031 / week

                                                                              Book View

                                                                              from £109 / night

                                                                              Distance approx 8.79 miles from Oakham Show on Map

                                                                              (22) Excellent 

                                                                              Certificate of Excellence

                                                                                17

                                                                                Holiday apartment in Stamford

                                                                                Lincolnshire / Stamford

                                                                                1 3 min stay varies

                                                                                • 1 bedroom
                                                                                • sleeps 3
                                                                                • min stay varies
                                                                                • Nearest beach 8 km
                                                                                • Child friendly
                                                                                • Private garden

                                                                                Certificate of Excellence

                                                                                from £86 / night

                                                                                £544 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 54 minutes

                                                                                from £86 / night

                                                                                Distance approx 17.98 miles from Oakham

                                                                                  22

                                                                                  Apartment rental in Leicester

                                                                                  Leicestershire / Leicester

                                                                                  1 4 2 nights min

                                                                                  • 1 bedroom
                                                                                  • sleeps 4
                                                                                  • 2 nights min
                                                                                  • Child friendly

                                                                                  from £79 / night

                                                                                  £553 / week

                                                                                  Book View

                                                                                  from £79 / night

                                                                                  Top Destination reviews

                                                                                  The Chapel - Wing. RUTLAND.
                                                                                  A very peaceful and relaxing location.

                                                                                  The Chapel was an ideal place to stay for a few days. Ideal location for Rutland Water and other amenities in the area. … see more
                                                                                  Garden Apartment, Manton Lodge
                                                                                  Amazing dog friendly farm style apartment!

                                                                                  Home away from home. Stylish, à la cottage apartment with stunning views and amazing location for long walks just moments from Ruthland Water. Very pleasnat and helpful owner. This farm with animals around would be great fun for kids too. We enjoyed our stay and exploring the area. Very peaceful place to recharge your batteries. Extremely comfortable bed and cute bird feeder outside our window are our favourites! Thank you Carolinesee 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
                                                                                  Sticky End - Thatched Rutland Luxury Holiday Cottage
                                                                                  charming, well equipped cottage in the heart of Rutland

                                                                                  The cottage was charming from the moment we opened the gate into the front yard, which was a real sun trap and haven of glorious plants. The cottage itself was beautifully furnished, outstandingly equipped and very comfortable. We had a most enjoyable stay with 2 children, and would definitely recommend the house to anyone with a love of antiques, quirky ness and accessibility to all the nearby places of interest. Lots of information about where to visit and what to see, all in all a super holiday with super accommodation.see more

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