Cheltenham Holidays & City Breaks - Holiday Lettings

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

Filters applied: City breaks

127 properties suitable for city breaks and holidays

(3) Very Good 

    19

    Cottage rental in Cheltenham

    Cotswolds / Cheltenham

    3 6 min stay varies

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

    from £102 / night

    £790 - £939 / week

    Book View

    Responds fast!
    avg. 3 hours 51 minutes

    from £102 / night

    (3) Excellent 

      17

      Apartment rental in Cheltenham with golf nearby

      Cotswolds / Cheltenham

      2 4 2 nights min

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

      from £161 / night

      £954 / week

      Book View

      Responds fast!
      avg. 3 hours 54 minutes

      from £161 / night

      (15) Very Good 

      Certificate of Excellence

        19

        Holiday cottage with golf nearby in Cheltenham

        Cotswolds / Cheltenham

        1 2 min stay varies

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

        Certificate of Excellence

        from £63 / night

        £355 - £418 / week

        Book View

        Responds fast!
        avg. 3 hours 51 minutes

        from £63 / night

        (66) Excellent 

        Certificate of Excellence

          23

          Holiday home rental

          Cotswolds / Cheltenham

          2 4 min stay varies

          • 2 bedrooms
          • sleeps 4
          • min stay varies
          • Child friendly
          • Ask about pets
          • Private garden
          “Idyllic!” Stayed at the Dovecot with my husband and 1 year old daughter. The property itself is beautiful - full of character and very well furnished. The location too is fantastic, right on a duck pond (safely fenced off for little ones) which my daughter loved. The property is a separate building on the owners farm (far away enough from the main building for privacy) - there are horses on the farm which in the evening came up close to the property (still fenced off though) which was lovely. We felt very well looked after by the owners - plenty of information on local attractions was provided, and best of all, a home made chocolate cake waiting for us when we arrived! Having forgotten our high chair, the owner lent us her own which was much appreciated. Location wise - we had a car, which was necessary for what we wanted to do - although I think there were probably plenty of walks in the area. We visited Tewkesbury which was VERY close), Cheltenham, Stow-on-the Wold and Bourton-on-the-Water all very easily from our base. Would definitely stay here again - and probably for a longer period of time.

          Certificate of Excellence

          from £144 / night

          £573 - £1,374 / week

          Book View

          Responds fast!
          avg. 2 hours 6 minutes

          from £144 / night

          (4) Excellent 

            27

            Cheltenham holiday apartment rental

            Cotswolds / Cheltenham

            2 6 1 night min

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

            from £114 / night

            £794 / week

            Book View

            from £114 / night

            (6) Excellent 

              19

              Holiday apartment in Montpellier suburb

              Cheltenham / Montpellier suburb

              2 4 2 nights min

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

              from £292 / night

              £1,432 - £1,579 / week

              Book View

              from £292 / night

                19

                Cheltenham holiday apartment rental

                Cotswolds / Cheltenham

                1 2 1 night min

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

                from £83 / night

                £344 / week

                Book View

                Responds fast!
                avg. 34 minutes

                from £83 / night

                (16) Excellent 

                Certificate of Excellence

                  21

                  Home rental in Prestbury

                  Cheltenham / Prestbury

                  6 16 min stay varies

                  • 6 bedrooms
                  • sleeps 16
                  • min stay varies
                  • Swimming pool
                  • Child friendly
                  • Car not necessary

                  Certificate of Excellence

                  from £1,374 / night

                  £5,153 / week

                  Book View

                  Responds fast!
                  avg. 3 hours 13 minutes

                  from £1,374 / night

                    28

                    Apartment rental in Cheltenham

                    Cotswolds / Cheltenham

                    2 6 1 night min

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

                    from £114 / night

                    £794 / week

                    Book View

                    from £114 / night

                      12

                      Cheltenham holiday home rental

                      Cotswolds / Cheltenham

                      2 6 2 nights min

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

                      from £115 / night

                      £802 - £962 / week

                      Book View

                      from £115 / night

                      (4) Excellent 

                        17

                        Holiday apartment in Cheltenham

                        Cotswolds / Cheltenham

                        2 5 min stay varies

                        • 2 bedrooms
                        • sleeps 5
                        • min stay varies
                        • Child friendly
                        • Car not necessary
                        • Private garden

                        from £184 / night

                        £916 / week

                        Book View

                        Responds fast!
                        avg. 2 hours 0 minutes

                        from £184 / night

                        (23) Very Good 

                          12

                          Holiday apartment rental

                          Cheltenham / Cheltenham

                          1 4 min stay varies

                          • 1 bedroom
                          • sleeps 4
                          • min stay varies
                          • Nearest beach 90 km
                          • Child friendly
                          • Car not necessary
                          “UNRIVALLED” Our group has stayed in this apartment for the Cheltenham races over the last 7 years or so and to a man would never consider staying anywhere else in the Town.It is ideally located for the Town centre and racecourse and has many other local attractions. The apartment is beautifully decorated and spotlessly clean and the icing on the cake is the fact that the owners are just about the most hospitable and friendly people we have ever encountered on our travels to the extent that they even invite us up on our last day for a Champagne breakfast. Believe me when i say that this accomodation and its owners will guarantee you a fantastic break.

                          from £75 / night

                          £521 / week

                          Book View

                          Responds fast!
                          avg. 20 minutes

                          from £75 / night

                          (5) Very Good 

                            10

                            Holiday apartment in Montpellier suburb

                            Cheltenham / Montpellier suburb

                            2 4 2 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 2 nights min
                            • Nearest beach 94 km
                            • Child friendly
                            • Car not necessary

                            from £207 / night

                            £1,088 / week

                            Book View

                            from £207 / night

                            (14) Very Good 

                              8

                              Apartment rental in Montpellier suburb with golf nearby

                              Cheltenham / Montpellier suburb

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Suitable for children age 5+
                              • Car not necessary

                              from £171 / night

                              £670 - £991 / week

                              Book View

                              Responds fast!
                              avg. 55 minutes

                              from £171 / night

                                9

                                Cottage rental in Leckhampton

                                Cheltenham / Leckhampton

                                2 4 20 nights min

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

                                from £184 / night

                                £1,042 / week

                                Book View

                                from £184 / night

                                  12

                                  Holiday home in Cheltenham

                                  Cheltenham / Cheltenham

                                  3 4 min stay varies

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

                                  from £115 / night

                                  £659 / week

                                  Book View

                                  Responds fast!
                                  avg. 2 hours 41 minutes

                                  from £115 / night

                                    39

                                    Holiday home in Cheltenham

                                    Cotswolds / Cheltenham

                                    6 12 min stay varies

                                    • 6 bedrooms
                                    • sleeps 12
                                    • min stay varies
                                    • Nearest beach 88 km
                                    • Child friendly
                                    • Car not necessary

                                    from £344 / night

                                    £2,405 / week

                                    Book View

                                    from £344 / night

                                      10

                                      Holiday apartment in Cheltenham

                                      Cotswolds / Cheltenham

                                      2 3 5 nights min

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

                                      from £138 / night

                                      £516 / week

                                      Book View

                                      Responds fast!
                                      avg. 2 hours 41 minutes

                                      from £138 / night

                                        8

                                        Holiday apartment in Cheltenham

                                        Cotswolds / Cheltenham

                                        2 4 2 nights min

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

                                        from £115 / night

                                        £802 / week

                                        Book View

                                        from £115 / night

                                        (6)  

                                          15

                                          Holiday apartment rental

                                          Cheltenham / Cheltenham

                                          1 3 min stay varies

                                          • 1 bedroom
                                          • sleeps 3
                                          • min stay varies
                                          • Child friendly
                                          • Car not necessary

                                          from £86 / night

                                          £458 - £544 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 48 minutes

                                          from £86 / night

                                          (3) Very Good 

                                            22

                                            Charlton Kings holiday studio rental

                                            Cheltenham / Charlton Kings

                                            Studio 2 min stay varies

                                            • Studio
                                            • sleeps 2
                                            • min stay varies
                                            • Ask about pets

                                            from £63 / night

                                            £344 / week

                                            Book View

                                            Responds fast!
                                            avg. 34 minutes

                                            from £63 / night

                                              13

                                              Holiday home accommodation

                                              Cheltenham / Cheltenham

                                              3 6 min stay varies

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

                                              from £229 / night

                                              £687 / week

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 41 minutes

                                              from £229 / night

                                              (2) Average 

                                                15

                                                Holiday home with golf nearby in Pittville

                                                Cheltenham / Pittville

                                                5 10 min stay varies

                                                • 5 bedrooms
                                                • sleeps 10
                                                • min stay varies
                                                • Child friendly
                                                • Car not necessary
                                                • Private garden

                                                from £344 / night

                                                £1,374 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 41 minutes

                                                from £344 / night

                                                  9

                                                  Holiday home rental

                                                  Cotswolds / Cheltenham

                                                  6 20 2 nights min

                                                  • 6 bedrooms
                                                  • sleeps 20
                                                  • 2 nights min
                                                  • Child friendly
                                                  • Private garden

                                                  from £1,718 / night

                                                  £12,023 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 47 minutes

                                                  from £1,718 / night

                                                    15

                                                    Holiday home rental

                                                    Cheltenham / Pittville

                                                    4 6 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Child friendly
                                                    • Car not necessary
                                                    • Private garden

                                                    from £207 / night

                                                    £859 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 2 hours 41 minutes

                                                    from £207 / night

                                                    (3) Average 

                                                      14

                                                      Cheltenham holiday apartment rental

                                                      Cheltenham / Cheltenham

                                                      2 6 min stay varies

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

                                                      from £103 / night

                                                      £745 - £974 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 48 minutes

                                                      from £103 / night

                                                      (1) Excellent 

                                                        7

                                                        Holiday home in Guiting Power

                                                        Cheltenham / Guiting Power

                                                        3 5 min stay varies

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

                                                        from £256 / night

                                                        £1,102 - £1,504 / week

                                                        Book View

                                                        from £256 / night

                                                        (1) Excellent 

                                                          43

                                                          Holiday home rental

                                                          Cotswolds / Cheltenham

                                                          5 9 1 night min

                                                          • 5 bedrooms
                                                          • sleeps 9
                                                          • 1 night min
                                                          • Ask owner if suitable for children
                                                          • Ask about pets
                                                          • Private garden

                                                          from £630 / night

                                                          £3,664 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 18 minutes

                                                          from £630 / night

                                                          Great rentals within 20 miles that match your search

                                                          Distance approx 16.23 miles from Cheltenham

                                                            15

                                                            Holiday camper van in Dymock

                                                            Forest of Dean / Dymock

                                                            1 5 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 5
                                                            • min stay varies
                                                            • Child friendly

                                                            from £75 / night

                                                            £573 - £974 / week

                                                            Book View

                                                            from £75 / night

                                                            Distance approx 15.81 miles from Cheltenham

                                                            (19) Very Good 

                                                              15

                                                              Blockley holiday cottage rental

                                                              Moreton-in-Marsh / Blockley

                                                              1 2 3 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 3 nights min
                                                              • Nearest beach 126 km
                                                              • Private garden

                                                              from £152 / night

                                                              £1,058 / week

                                                              Book View

                                                              from £152 / night

                                                              Distance approx 16.53 miles from Cheltenham

                                                              (6) Excellent 

                                                                10

                                                                Barn rental in Longhope

                                                                Gloucestershire / Longhope

                                                                1 2 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 3 nights min
                                                                • Ask owner if suitable for children
                                                                • Private garden

                                                                from £86 / night

                                                                £602 / week

                                                                Book View

                                                                from £86 / night

                                                                Distance approx 19.38 miles from Cheltenham

                                                                (27) Very Good 

                                                                  40

                                                                  Cottage rental in Stratford-upon-Avon with golf nearby, tennis court

                                                                  Warwickshire / Stratford-upon-Avon

                                                                  5 10 min stay varies

                                                                  • 5 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child friendly
                                                                  • Pet friendly

                                                                  from £249 / night

                                                                  £1,199 - £3,199 / week

                                                                  Enquire View

                                                                  from £249 / night

                                                                  Distance approx 12.28 miles from Cheltenham

                                                                  (8) Excellent 

                                                                    21

                                                                    Holiday apartment rental

                                                                    Stroud / Chalford

                                                                    2 5 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 5
                                                                    • min stay varies
                                                                    • Child friendly
                                                                    • Car not necessary
                                                                    • Private garden

                                                                    from £75 / night

                                                                    £682 - £802 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 3 hours 17 minutes

                                                                    from £75 / night

                                                                    Distance approx 15.42 miles from Cheltenham

                                                                    (54) Excellent 

                                                                      23

                                                                      Holiday cottage rental

                                                                      Cotswolds / Stow-on-the-Wold

                                                                      2 5 2 nights min

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

                                                                      from £144 / night

                                                                      £1,002 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 25 minutes

                                                                      from £144 / night

                                                                      Distance approx 17.74 miles from Cheltenham

                                                                      (1) Excellent 

                                                                        38

                                                                        Holiday cottage with shared pool in Somerford Keynes

                                                                        Cirencester / Somerford Keynes

                                                                        4 6 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £138 / night

                                                                        £859 - £1,626 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 1 hour 32 minutes

                                                                        from £138 / night

                                                                        Distance approx 15.21 miles from Cheltenham

                                                                        (1) Excellent 

                                                                          22

                                                                          Holiday home in Evesham

                                                                          Worcestershire / Evesham

                                                                          3 6 3 nights min

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

                                                                          from £103 / night

                                                                          £630 - £1,031 / week

                                                                          Book View

                                                                          from £103 / night

                                                                          Distance approx 11.76 miles from Cheltenham

                                                                          (1) Excellent 

                                                                            23

                                                                            Tibberton holiday home rental

                                                                            Gloucestershire / Tibberton

                                                                            1 2 3 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 3 nights min
                                                                            • Child friendly
                                                                            • Private garden

                                                                            from £109 / night

                                                                            £419 - £1,028 / week

                                                                            Enquire View

                                                                            from £109 / night

                                                                            Distance approx 18.37 miles from Cheltenham

                                                                            (8) Excellent 

                                                                            Certificate of Excellence

                                                                              30

                                                                              Holiday apartment in Great Malvern

                                                                              Malvern / Great Malvern

                                                                              2 4 3 nights min

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

                                                                              Certificate of Excellence

                                                                              from £126 / night

                                                                              £802 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 16 minutes

                                                                              from £126 / night

                                                                              Distance approx 19.31 miles from Cheltenham

                                                                              (18) Excellent 

                                                                                23

                                                                                Tetbury holiday home rental

                                                                                Cotswolds / Tetbury

                                                                                4 8 min stay varies

                                                                                • 4 bedrooms
                                                                                • sleeps 8
                                                                                • min stay varies
                                                                                • Nearest beach 16 km
                                                                                • Child friendly
                                                                                • Pet friendly

                                                                                from £335 / night

                                                                                £1,338 - £2,569 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 3 hours 11 minutes

                                                                                from £335 / night

                                                                                Distance approx 15.98 miles from Cheltenham

                                                                                  23

                                                                                  Holiday camper van in Dymock

                                                                                  Forest of Dean / Dymock

                                                                                  1 5 min stay varies

                                                                                  • 1 bedroom
                                                                                  • sleeps 5
                                                                                  • min stay varies
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £75 / night

                                                                                  £573 - £974 / week

                                                                                  Book View

                                                                                  from £75 / night

                                                                                  Also consider