Apartments in Cheltenham and Self catering accommodation - Holiday Lettings - Holiday Rentals Cheltenham

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

1,511 Holiday homes

(55) Excellent 

    40

    Holiday farmhouse in Cheltenham

    Cheltenham / Cheltenham

    5 10 min stay varies

    • 5 bedrooms
    • sleeps 10
    • min stay varies
    • Child friendly
    • Ask about pets
    • Private garden
    “Beautiful property with incredible stunning views” Bushcombe House Farm is a beautiful property in a peaceful location with incredible stunning views, obviously a lot of love and attention to detail has gone into this property and it has everything that you could wish for and truly is a most wonderful place to stay. The location is within easy reach of all shops and amenities and a short walk uphill to Cleeve Common. We thoroughly enjoyed our stay and didn't want to leave and we are hoping to return soon. Thank you Peter & Lyn.

    from £300 / night

    £1,650 - £2,000 / week

    Book View

    from £300 / night

    (8) Excellent 

      9

      Holiday cottage with golf nearby in Cheltenham

      Cheltenham / Cheltenham

      1 2 min stay varies

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

      from £75 / night

      £378 - £481 / week

      Book View

      Responds fast!
      avg. 3 hours 56 minutes

      from £75 / night

      (8) Very Good 

        16

        Holiday cottage in Cheltenham

        Cotswolds / Cheltenham

        2 4 min stay varies

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

        from £109 / night

        £516 - £630 / week

        Book View

        Responds fast!
        avg. 3 hours 56 minutes

        from £109 / night

        (24) Excellent 

          25

          Holiday cottage with golf nearby in Cleeve Hill

          Cheltenham / Cleeve Hill

          4 10 min stay varies

          • 4 bedrooms
          • sleeps 10
          • min stay varies
          • Child friendly
          • Pet friendly
          • Private garden

          from £170 / night

          £850 - £1,650 / week

          Book View

          Responds fast!
          avg. 2 hours 5 minutes

          from £170 / night

          (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 £132 / night

            £859 - £939 / week

            Book View

            Responds fast!
            avg. 3 hours 56 minutes

            from £132 / 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

              (14) Very Good 

                19

                Holiday cottage with golf nearby in Cheltenham

                Cotswolds / Cheltenham

                1 2 min stay varies

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

                from £75 / night

                £401 - £481 / week

                Book View

                Responds fast!
                avg. 3 hours 56 minutes

                from £75 / night

                (3) Excellent 

                  16

                  Cheltenham holiday apartment rental

                  Cotswolds / Cheltenham

                  1 2 2 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 2 nights min
                  • Car not necessary

                  from £115 / night

                  £687 / week

                  Book View

                  Responds fast!
                  avg. 3 hours 13 minutes

                  from £115 / night

                  (64) 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 44 minutes

                    from £144 / night

                    (3) Very Good 

                      13

                      Holiday cottage letting

                      Cotswolds / Cheltenham

                      1 2 3 nights min

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

                      from £75 / night

                      £367 - £481 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 56 minutes

                      from £75 / 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

                        (3) Very Good 

                          28

                          Charlton Kings holiday apartment rental

                          Cheltenham / Charlton Kings

                          1 2 1 night min

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

                          from £58 / night

                          £344 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 34 minutes

                          from £58 / night

                          (29) Excellent 

                            34

                            Home rental in Montpellier suburb

                            Cheltenham / Montpellier suburb

                            5 9 2 nights min

                            • 5 bedrooms
                            • sleeps 9
                            • 2 nights min
                            • Child friendly
                            • Private garden

                            from £373 / night

                            £5,153 - £5,317 / week

                            Book View

                            from £373 / night

                            (6) Excellent 

                              11

                              Holiday apartment in Cheltenham

                              Cotswolds / Cheltenham

                              2 4 3 nights min

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

                              from £207 / night

                              £1,260 / week

                              Book View

                              from £207 / night

                              (5) 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 £207 / night

                                £1,260 - £1,408 / week

                                Book View

                                from £207 / night

                                (14) Excellent 

                                  23

                                  Cheltenham holiday apartment rental

                                  Cheltenham / Cheltenham

                                  1 2 2 nights min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 2 nights min
                                  • Car not necessary
                                  • Air conditioning

                                  from £163 / night

                                  £899 / week

                                  Book View

                                  from £163 / night

                                  (10) Excellent 

                                    20

                                    Holiday cottage with golf nearby in Charlton Kings

                                    Cheltenham / Charlton Kings

                                    3 6 min stay varies

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

                                    from £115 / night

                                    £630 - £722 / week

                                    Book View

                                    from £115 / 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. 38 minutes

                                      from £83 / night

                                        13

                                        Cleeve Hill holiday home rental

                                        Cheltenham / Cleeve Hill

                                        2 2 7 nights min

                                        • 2 bedrooms
                                        • sleeps 2
                                        • 7 nights min
                                        • Child friendly
                                        • Pet friendly
                                        • Private garden

                                        from £56 / night

                                        £387 - £995 / week

                                        Enquire View

                                        from £56 / night

                                        (8) Excellent 

                                          28

                                          Holiday apartment in Cheltenham

                                          Cotswolds / Cheltenham

                                          1 2 2 nights min

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

                                          from £92 / night

                                          £642 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 44 minutes

                                          from £92 / night

                                            19

                                            Holiday cottage in Shurdington

                                            Cheltenham / Shurdington

                                            1 2 7 nights min

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

                                            from £69 / night

                                            £483 - £940 / week

                                            Enquire View

                                            from £69 / night

                                            (6) Very Good 

                                              6

                                              Holiday barn in Cheltenham

                                              Cheltenham / Cheltenham

                                              1 2 2 nights min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 2 nights min

                                              from £92 / night

                                              £401 / week

                                              Book View

                                              Responds fast!
                                              avg. 3 hours 27 minutes

                                              from £92 / night

                                              (1) Excellent 

                                                13

                                                Holiday apartment in Cheltenham

                                                Cotswolds / Cheltenham

                                                1 3 3 nights min

                                                • 1 bedroom
                                                • sleeps 3
                                                • 3 nights min

                                                from £115 / night

                                                £687 / week

                                                Book View

                                                Responds fast!
                                                avg. 2 hours 16 minutes

                                                from £115 / 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

                                                      22

                                                      Holiday apartment in Cheltenham

                                                      Cotswolds / Cheltenham

                                                      1 2 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • min stay varies
                                                      • Car not necessary

                                                      from £86 / night

                                                      £602 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 1 hour 55 minutes

                                                      from £86 / night

                                                      (22) Excellent 

                                                      Certificate of Excellence

                                                        20

                                                        Cheltenham holiday barn rental

                                                        Cotswolds / Cheltenham

                                                        4 8 2 nights min

                                                        • 4 bedrooms
                                                        • sleeps 8
                                                        • 2 nights min
                                                        • Child friendly
                                                        • Private garden
                                                        “A wonderful location away from everything - perfect for family get togethers.” My husband and I and our two children stayed at Southwold Barn for a week in August. We invited along all the grandparents also. There was plenty of room for us all and the barn was extremely well catered for...even down to books and board games should you require any further entertainment. We ate in every evening and even made use of the BBQ too. The kitchen was very well stocked and there was everything that you could ever need. Great that we had the use of wifi and the TV's were great also. Emma (who lives next door) was extremely helpful whenever we had any queries and very understanding when we explained our two year old daughter had attempted to paint her nails but instead had painted the duvet! Emma also welcomed us with an amazing lemon drizzle cake. We visited a different place everyday. My favourites would be Adam Henson's Cotswold Farm, Circencester and Burton on the water. There are lovely pubs nearby Garniche and one in North Leach called the wheat sheaf. Great food here and some wonderful walks. We also visited Chedworth Roman Villa which is run by the National Trust. All in all a fabulous relaxing holiday. Did I mention that we loved Mack the peacock, Rosie the duck and her ducklings, the sheep, hens and the cockerel! A fantastic holiday you won't be disappointed!

                                                        Certificate of Excellence

                                                        from £331 / night

                                                        £1,302 - £2,453 / week

                                                        Book View

                                                        from £331 / night

                                                        (3) Very Good 

                                                          16

                                                          Home rental in Cheltenham

                                                          Cotswolds / Cheltenham

                                                          1 2 min stay varies

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • min stay varies
                                                          • Nearest beach 30 km
                                                          • Car not necessary
                                                          • Private garden

                                                          from £92 / night

                                                          £481 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 13 minutes

                                                          from £92 / night

                                                          (16) Excellent 

                                                          Certificate of Excellence

                                                            14

                                                            Holiday studio in Cheltenham

                                                            Cheltenham / Cheltenham

                                                            Studio 2 min stay varies

                                                            • Studio
                                                            • sleeps 2
                                                            • min stay varies

                                                            Certificate of Excellence

                                                            from £68 / night

                                                            £338 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 1 hour 59 minutes

                                                            from £68 / night

                                                              22

                                                              Holiday apartment rental

                                                              Cheltenham / Charlton Kings

                                                              2 4 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Child friendly
                                                              • Ask about pets
                                                              • Private garden

                                                              from £516 / night

                                                              £3,607 / week

                                                              Book View

                                                              from £516 / night

                                                              (22) 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. 19 minutes

                                                                from £75 / night

                                                                (1) Excellent 

                                                                  13

                                                                  Cheltenham holiday apartment rental

                                                                  Cheltenham / Cheltenham

                                                                  3 6 2 nights min

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

                                                                  from £251 / night

                                                                  £1,443 - £1,603 / week

                                                                  Book View

                                                                  from £251 / 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

                                                                    (5) Very Good 

                                                                      9

                                                                      Holiday b&b in Cheltenham

                                                                      Cotswolds / Cheltenham

                                                                      4 8 1 night min

                                                                      • 4 bedrooms
                                                                      • sleeps 8
                                                                      • 1 night min
                                                                      • Child friendly
                                                                      • Pet friendly
                                                                      • Private garden

                                                                      from £115 / night

                                                                      £745 - £3,269 / week

                                                                      Book View

                                                                      from £115 / 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 £184 / night

                                                                        £1,088 - £1,123 / week

                                                                        Book View

                                                                        from £184 / night

                                                                        (1) Very Good 

                                                                          5

                                                                          Apartment rental in Montpellier suburb

                                                                          Cheltenham / Montpellier suburb

                                                                          1 2 2 nights min

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

                                                                          from £144 / night

                                                                          £997 / week

                                                                          Book View

                                                                          from £144 / night

                                                                            29

                                                                            Holiday apartment in Cheltenham

                                                                            Cotswolds / Cheltenham

                                                                            2 4 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • min stay varies

                                                                            from £172 / night

                                                                            £2,577 - £6,298 / week

                                                                            Book View

                                                                            from £172 / night

                                                                            (2) Very Good 

                                                                              18

                                                                              Holiday home in Cheltenham

                                                                              Cotswolds / Cheltenham

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min

                                                                              from £103 / night

                                                                              £573 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 39 minutes

                                                                              from £103 / 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

                                                                                (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. 1 hour 34 minutes

                                                                                  from £171 / night

                                                                                  Why Cheltenham?

                                                                                  The Regency town of Cheltenham is perfect for those looking for a sophisticated getaway that's not too far from the rolling hills of the countryside.

                                                                                  Select a holiday rental in Cheltenham, and start planning your trip to one of England's most famous spa towns.

                                                                                  About Cheltenham

                                                                                  Cheltenham's history spans back centuries, and has always been a popular tourist spot thanks to the mineral springs that flow here.

                                                                                  The town itself is on the edge of the Cotswolds and is an area of outstanding natural beauty. Many choose to hike and roam through the hills to check out the views. If you go, don't forget your camera as there are plenty of photo-op spots along the trails.

                                                                                  What to Do

                                                                                  There are galleries, theatres and museums throughout the town, so why not visit one? The Wilson is among the most popular.

                                                                                  Top Cheltenham Travel Tips

                                                                                  Cheltenham is known all over the world for being a hive of culture and excitement. Each year, thousands flock here for the horse racing, jazz, and food & drink festivals. See if you can time your holiday to coincide with one of these. It's well worth it for the atmosphere.

                                                                                  Cheltenham is a wonderful place where you can wander around to your heart's content. Book your holiday rental in Cheltenham and let the adventure begin.

                                                                                  Top Destination reviews

                                                                                  St Luke's 1 Bed Apartment
                                                                                  Excellent

                                                                                  Very clean, homely and new property. Would highly recommend. Only stoped for 1 night but very comfortable. Nearby pubs and restaurants. … see more
                                                                                  The Dovecote
                                                                                  Dovecote holiday

                                                                                  What a beautiful, clean, quiet location highly recommended definitely on our list to visit again, owner was super welcoming and helpful. … see more
                                                                                  Spacious and comfortable apartment within walking distance of the town centre
                                                                                  Amazing property

                                                                                  Amazing property, clean, tidy, lovely decor. Great location. Perfect for a weekend with friends. Would highly recommend. Hope to visit again when we’re next in Cheltenham. … see more
                                                                                  Bushcombe House Farm Bushcombe Lane Woodmancote
                                                                                  Stunning views, outstanding accommodation

                                                                                  Perfect location, with beautiful views. Couldn't of asked for much more. Kitchen had everything you need. Plenty of rooms for gatherings, and great comfy beds. Have recommended to lots! Will definitely be back. … see more
                                                                                  Cotswold Manor House Apartment, overlooking Cheltenham
                                                                                  So so lovely - the photos don't do it justice

                                                                                  The location is perfect being so close to Cheltenham, but feeling like a proper country getaway too. The views are beautiful, the apartment is large, but with a cosy feel - very luxurious too. The family welcomed us and were very helpful and lovely. Me and my friends had a fab time and are hoping to visit again next year :)see more
                                                                                  Forge Cottage is a lovely Cotswold stone property, managed by the Guest House
                                                                                  lovely cosy cottage

                                                                                  Everything you need is provided for you, including a picnic basket and rug! Sadly the weather wasn't great for us, but we hope to return, so maybe we will get to use it next time. The village is so pretty and it was brilliant to be able to walk to one of the local pub, the Hollow Bottom which had a great atmosphere and lovely food. A great location, cosy and welcoming, great communication, what more could you want.see more

                                                                                  Also consider