Houses in Uppingham and Apartments – Holiday Lettings - Holiday Rentals Uppingham

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

215 Holiday homes

(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

    £705 - £911 / week

    Book View

    from £132 / 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

      (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

        (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

          (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

            (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

              (1) Excellent 

                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 3 minutes

                from £115 / night

                  26

                  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 £118 / night

                  £403 - £1,179 / week

                  Enquire View

                  from £118 / night

                  Great rentals within 20 miles that match your search

                  Distance approx 12.73 miles from Uppingham

                  (16) Very Good 

                    13

                    Stamford holiday converted chapel rental

                    Lincolnshire / Stamford

                    2 4 min stay varies

                    • 2 bedrooms
                    • sleeps 4
                    • min stay varies
                    • Nearest beach 13 km
                    • Child friendly
                    • Pet friendly

                    from £115 / night

                    £630 - £916 / week

                    Book View

                    Responds fast!
                    avg. 1 hour 57 minutes

                    from £115 / night

                    Distance approx 5.54 miles from Uppingham Show on Map

                    (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

                      Certificate of Excellence

                      from £115 / night

                      £544 - £802 / week

                      Book View

                      from £115 / night

                      Distance approx 5.57 miles from Uppingham Show on Map

                      (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

                        Distance approx 2.67 miles from Uppingham Show on Map

                        (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

                          Distance approx 13.29 miles from Uppingham

                          (10) Excellent 

                            31

                            Holiday barn in Aunby

                            Stamford / Aunby

                            2 4 min stay varies

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

                            from £138 / night

                            £630 - £745 / week

                            Book View

                            Responds fast!
                            avg. 2 hours 30 minutes

                            from £138 / night

                            Distance approx 17.31 miles from Uppingham

                            (3) Very Good 

                              14

                              Apartment rental in Leicester

                              Leicestershire / Leicester

                              2 4 4 nights min

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

                              from £98 / night

                              £682 / week

                              Book View

                              from £98 / night

                              Distance approx 13.29 miles from Uppingham

                              (4) Excellent 

                              Certificate of Excellence

                                21

                                Stamford holiday home rental

                                Lincolnshire / Stamford

                                4 8 min stay varies

                                • 4 bedrooms
                                • sleeps 8
                                • min stay varies
                                • Nearest beach 100 km
                                • Child friendly

                                Certificate of Excellence

                                from £252 / night

                                £1,088 - £1,718 / week

                                Book View

                                Responds fast!
                                avg. 2 hours 30 minutes

                                from £252 / night

                                Distance approx 19.33 miles from Uppingham

                                (2) Very Good 

                                  28

                                  Peterborough holiday apartment rental

                                  Cambridgeshire / Peterborough

                                  2 6 2 nights min

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

                                  from £102 / night

                                  £714 - £1,315 / week

                                  Book View

                                  Responds fast!
                                  avg. 3 hours 46 minutes

                                  from £102 / night

                                  Distance approx 12.06 miles from Uppingham

                                    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

                                    Distance approx 12.04 miles from Uppingham

                                      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 17.54 miles from Uppingham

                                        12

                                        Holiday apartment in Leicester

                                        Leicestershire / Leicester

                                        1 4 2 nights min

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

                                        from £75 / night

                                        £521 / week

                                        Book View

                                        from £75 / night

                                        Distance approx 17.9 miles from Uppingham

                                          8

                                          Apartment letting in Leicester

                                          Leicestershire / Leicester

                                          1 6 2 nights min

                                          • 1 bedroom
                                          • sleeps 6
                                          • 2 nights min

                                          from £92 / night

                                          £577 / week

                                          Book View

                                          from £92 / night

                                          Distance approx 13.07 miles from Uppingham

                                            19

                                            Holiday home in Kettering

                                            Northamptonshire / Kettering

                                            4 7 1 night min

                                            • 4 bedrooms
                                            • sleeps 7
                                            • 1 night min
                                            • Child friendly

                                            from £114 / night

                                            £794 / week

                                            Book View

                                            Responds fast!
                                            avg. 42 minutes

                                            from £114 / night

                                            Distance approx 15.65 miles from Uppingham

                                              45

                                              Holiday guest house rental

                                              Northamptonshire / Kettering

                                              1 2 1 night min

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

                                              from £91 / night

                                              £401 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 3 minutes

                                              from £91 / night

                                              Distance approx 16.2 miles from Uppingham

                                              (2) Very Good 

                                                26

                                                Lodge rental in Market Harborough

                                                Leicestershire / Market Harborough

                                                2 4 3 nights min

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

                                                from £138 / night

                                                £866 / week

                                                Book View

                                                from £138 / night

                                                Distance approx 13.04 miles from Uppingham

                                                  1

                                                  Holiday apartment in Kettering

                                                  Northamptonshire / Kettering

                                                  2 3 1 night min

                                                  • 2 bedrooms
                                                  • sleeps 3
                                                  • 1 night min
                                                  • Child friendly

                                                  from £86 / night

                                                  £602 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 42 minutes

                                                  from £86 / night

                                                  Distance approx 18.62 miles from Uppingham

                                                    5

                                                    Holiday b&b in Melton Mowbray

                                                    Leicestershire / Melton Mowbray

                                                    1 2 1 night min

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

                                                    from £46 / night

                                                    £321 / week

                                                    Book View

                                                    from £46 / night

                                                    Distance approx 5.4 miles from Uppingham Show on Map

                                                    (4) Excellent 

                                                      7

                                                      Stamford holiday apartment rental

                                                      Lincolnshire / Stamford

                                                      1 2 14 nights min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 14 nights min
                                                      • Ask owner if suitable for children
                                                      • Pet friendly

                                                      from £58 / night

                                                      £401 / week

                                                      Book View

                                                      from £58 / night

                                                      Distance approx 17.57 miles from Uppingham

                                                      (1) Very Good 

                                                        14

                                                        Leicester holiday apartment rental

                                                        Leicestershire / Leicester

                                                        2 6 1 night min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 1 night min
                                                        • Child friendly

                                                        from £126 / night

                                                        £882 / week

                                                        Book View

                                                        from £126 / night

                                                        Distance approx 11.11 miles from Uppingham

                                                          12

                                                          Holiday home in Stamford

                                                          Lincolnshire / Stamford

                                                          19 38 min stay varies

                                                          • 19 bedrooms
                                                          • sleeps 38
                                                          • min stay varies
                                                          • Child friendly
                                                          • Car not necessary
                                                          • Pet friendly

                                                          from £916 / night

                                                          £6,412 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 18 minutes

                                                          from £916 / night

                                                          Distance approx 15.65 miles from Uppingham

                                                            45

                                                            Holiday guest house rental

                                                            Northamptonshire / Kettering

                                                            1 2 1 night min

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

                                                            from £91 / night

                                                            £401 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 3 hours 3 minutes

                                                            from £91 / night

                                                            Distance approx 17.76 miles from Uppingham

                                                              7

                                                              Leicester holiday apartment rental

                                                              Leicestershire / Leicester

                                                              2 6 3 nights min

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

                                                              from £184 / night

                                                              £745 / week

                                                              Book View

                                                              from £184 / night

                                                              Distance approx 4.81 miles from Uppingham Show on Map

                                                                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

                                                                Distance approx 4.83 miles from Uppingham Show on Map

                                                                  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

                                                                  Distance approx 10.2 miles from Uppingham

                                                                  (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 17.4 miles from Uppingham

                                                                    (5) Excellent 

                                                                    Certificate of Excellence

                                                                      44

                                                                      Leicester holiday home rental

                                                                      Leicestershire / Leicester

                                                                      3 5 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 5
                                                                      • 7 nights min
                                                                      • Child friendly
                                                                      • Car not necessary
                                                                      • Private garden

                                                                      Certificate of Excellence

                                                                      from £121 / night

                                                                      £819 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 58 minutes

                                                                      from £121 / night

                                                                      Distance approx 17.58 miles from Uppingham

                                                                        5

                                                                        Leicester holiday apartment rental

                                                                        Leicestershire / Leicester

                                                                        1 4 2 nights min

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

                                                                        from £70 / night

                                                                        £489 / week

                                                                        Book View

                                                                        from £70 / night

                                                                        Distance approx 19.06 miles from Uppingham

                                                                          23

                                                                          Leicester holiday apartment rental

                                                                          Leicestershire / Leicester

                                                                          1 6 2 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Child friendly

                                                                          from £61 / night

                                                                          £425 / week

                                                                          Book View

                                                                          from £61 / night

                                                                          Distance approx 17.58 miles from Uppingham

                                                                            26

                                                                            Leicester holiday apartment rental

                                                                            Leicestershire / Leicester

                                                                            1 4 2 nights min

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

                                                                            from £67 / night

                                                                            £465 / week

                                                                            Book View

                                                                            from £67 / night

                                                                            Distance approx 19.66 miles from Uppingham

                                                                              36

                                                                              Holiday home in Anstey

                                                                              Leicester / Anstey

                                                                              4 8 1 night min

                                                                              • 4 bedrooms
                                                                              • sleeps 8
                                                                              • 1 night min
                                                                              • Child friendly

                                                                              from £124 / night

                                                                              £866 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 28 minutes

                                                                              from £124 / night

                                                                              Distance approx 17.58 miles from Uppingham

                                                                                20

                                                                                Apartment rental in Leicester

                                                                                Leicestershire / Leicester

                                                                                2 6 2 nights min

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

                                                                                from £79 / night

                                                                                £553 / week

                                                                                Book View

                                                                                from £79 / night

                                                                                Distance approx 19.72 miles from Uppingham

                                                                                  5

                                                                                  Wellingborough holiday apartment rental

                                                                                  Northamptonshire / Wellingborough

                                                                                  2 4 2 nights min

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

                                                                                  from £81 / night

                                                                                  £481 / week

                                                                                  Book View

                                                                                  from £81 / night

                                                                                  Top Destination reviews

                                                                                  Luxury Rutland House. 5 Bedrooms/Pool/Cinema room
                                                                                  Wonderful for a family get together!

                                                                                  So impressed by this house! It was perfect for my 50th birthday family celebration. So much space! Great to have the pool, sauna and hot tub..even the gym facilities and darts were used. The cinema room was brilliant too. So many bathrooms, great cooking facilities, large garden...I really can't fault the house. Katie was really helpful; explaining how to use all the facilities. I would really recommend this place and have great memories now of a fab weekend...thanks!see more
                                                                                  The Corner House, Uppingham, Rutland.
                                                                                  Perfect place to stay

                                                                                  A lovely house right in the centre of Uppingham. The rooms are perfectly furnished to make the stay homely, elegant and comfortable. Great for 3 couples or for a family reunion with small children included. We will be back. … see more
                                                                                  Delightful Ground Floor Apartment
                                                                                  Comfortable apartment in centre of Uppingham

                                                                                  The apartment is in the centre of Uppingham, just minutes walk from shops, pubs and restaurants. We enjoy our stays so much that we never look at other accommodation in the area. Uppingham won a gold medal for flower displays and the Spring flowers were beautiful. Oakham is a pleasant town and a little further is Stamford is beautiful. Rutland is a small but lovely county, 'Much in little'.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
                                                                                  Little Thatch, Seaton, Uppingham - Thatched Rutland Luxury Holiday Cottage
                                                                                  Delightful Chocolate Box Cottage

                                                                                  What a delightful cottage so quaint and pretty. Thank you to Martin and Julia for creating such gem of a place to stay in. The Kitchen is stocked with every utensil you can think of, there were tea, milk, coffee and luxury biscuits waiting for us on arrival. The cottage is home from home. It is a good base for visiting Rutland Water, Stamford, Oakham, Burleigh House, and Uppingham. Well done Martin and Julia on the presentation of the cottage as a whole.see more

                                                                                  Also consider