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

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1,505 Holiday homes

(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 £58 / night

    £332 - £481 / week

    Book View

    from £58 / night

    (23) 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. 3 hours 35 minutes

      from £170 / night

      (53) 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

        from £300 / night

        £1,550 - £1,750 / week

        Book View

        from £300 / 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

          from £161 / 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 £126 / night

            £573 - £939 / week

            Book View

            from £126 / night

            (6) Very Good 

              16

              Holiday cottage in Cheltenham

              Cotswolds / Cheltenham

              2 4 min stay varies

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

              from £90 / night

              £413 - £630 / week

              Book View

              from £90 / night

              (3) Excellent 

                16

                Cheltenham holiday apartment rental

                Cotswolds / Cheltenham

                1 2 min stay varies

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

                from £115 / night

                £687 / week

                Book View

                Responds fast!
                avg. 3 hours 13 minutes

                from £115 / 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 £58 / night

                  £332 - £481 / week

                  Book View

                  from £58 / night

                  (3) Very Good 

                    13

                    Holiday cottage letting

                    Cotswolds / Cheltenham

                    1 2 min stay varies

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

                    from £58 / night

                    £332 - £481 / week

                    Book View

                    from £58 / night

                    (63) 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

                      Certificate of Excellence

                      from £132 / night

                      £573 - £1,374 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 27 minutes

                      from £132 / night

                        42

                        Southam holiday home rental

                        Cheltenham / Southam

                        6 14 min stay varies

                        • 6 bedrooms
                        • sleeps 14
                        • min stay varies
                        • Child friendly

                        from £1,031 / night

                        £4,122 - £8,576 / week

                        Book View

                        from £1,031 / 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 £344 / night

                          £5,153 - £5,317 / week

                          Book View

                          from £344 / 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 - £2,732 / week

                            Book View

                            from £207 / 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 5 minutes

                                from £58 / night

                                (1) Excellent 

                                  45

                                  Holiday home in Cheltenham

                                  Cotswolds / Cheltenham

                                  7 20 min stay varies

                                  • 7 bedrooms
                                  • sleeps 20
                                  • min stay varies
                                  • Child friendly
                                  • Private garden

                                  from £1,489 / night

                                  £4,580 - £12,618 / week

                                  Book View

                                  from £1,489 / night

                                  (6) Excellent 

                                    11

                                    Holiday apartment in Cheltenham

                                    Cotswolds / Cheltenham

                                    2 4 min stay varies

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

                                    from £207 / night

                                    £1,260 / 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

                                          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 £50 / night

                                          £345 - £953 / week

                                          Enquire View

                                          from £50 / 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 £62 / night

                                            £433 - £898 / week

                                            Enquire View

                                            from £62 / night

                                            (8) Excellent 

                                              28

                                              Holiday apartment in Cheltenham

                                              Cotswolds / Cheltenham

                                              1 2 min stay varies

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

                                              from £86 / night

                                              £602 / week

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 44 minutes

                                              from £86 / 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. 51 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 £974 / night

                                                  £5,153 - £11,450 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 46 minutes

                                                  from £974 / night

                                                  (5) 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. 2 hours 40 minutes

                                                    from £92 / night

                                                      28

                                                      Apartment rental in Cheltenham

                                                      Cotswolds / Cheltenham

                                                      2 6 1 night min

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

                                                      from £98 / night

                                                      £682 / week

                                                      Book View

                                                      from £98 / night

                                                      (1) Excellent 

                                                        13

                                                        Holiday apartment in Cheltenham

                                                        Cotswolds / Cheltenham

                                                        1 3 min stay varies

                                                        • 1 bedroom
                                                        • sleeps 3
                                                        • min stay varies

                                                        from £115 / night

                                                        £687 - £1,432 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 2 hours 19 minutes

                                                        from £115 / night

                                                          30

                                                          Holiday cottage in Charlton Kings

                                                          Cheltenham / Charlton Kings

                                                          1 2 3 nights min

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

                                                          from £86 / night

                                                          £384 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 3 hours 19 minutes

                                                          from £86 / night

                                                            22

                                                            Holiday apartment in Cheltenham

                                                            Cotswolds / Cheltenham

                                                            1 2 2 nights min

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

                                                            from £81 / night

                                                            £561 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 3 hours 1 minutes

                                                            from £81 / night

                                                              16

                                                              Holiday apartment in Cheltenham

                                                              Cotswolds / Cheltenham

                                                              4 6 2 nights min

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

                                                              from £126 / night

                                                              £859 - £1,661 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 54 minutes

                                                              from £126 / night

                                                                20

                                                                Holiday home in Charlton Kings

                                                                Cheltenham / Charlton Kings

                                                                4 8 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Child friendly

                                                                from £336 / night

                                                                £1,248 - £2,703 / week

                                                                Book View

                                                                from £336 / night

                                                                (3) Very Good 

                                                                  16

                                                                  Home rental in Cheltenham

                                                                  Cotswolds / Cheltenham

                                                                  1 2 2 nights min

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

                                                                  from £92 / night

                                                                  £481 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 16 minutes

                                                                  from £92 / 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 min stay varies

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

                                                                      from £207 / night

                                                                      £1,088 / week

                                                                      Book View

                                                                      from £207 / night

                                                                        26

                                                                        Holiday home accommodation

                                                                        Cheltenham / Cleeve Hill

                                                                        5 14 min stay varies

                                                                        • 5 bedrooms
                                                                        • sleeps 14
                                                                        • min stay varies
                                                                        • Child friendly

                                                                        from £1,203 / night

                                                                        £5,210 - £15,664 / week

                                                                        Book View

                                                                        from £1,203 / night

                                                                          12

                                                                          Cheltenham holiday home rental

                                                                          Cotswolds / Cheltenham

                                                                          2 6 min stay varies

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

                                                                          from £115 / night

                                                                          £802 - £962 / week

                                                                          Book View

                                                                          from £115 / 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. 2 hours 24 minutes

                                                                            from £68 / night

                                                                            (1) Very Good 

                                                                              5

                                                                              Apartment rental in Montpellier suburb

                                                                              Cheltenham / Montpellier suburb

                                                                              1 2 min stay varies

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

                                                                              from £166 / night

                                                                              £997 / week

                                                                              Book View

                                                                              from £166 / night

                                                                              (4) Excellent 

                                                                                17

                                                                                Holiday apartment in Cheltenham

                                                                                Cotswolds / Cheltenham

                                                                                2 5 1 night min

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

                                                                                from £184 / night

                                                                                £916 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 39 minutes

                                                                                from £184 / 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

                                                                                  Certificate of Excellence

                                                                                  from £331 / night

                                                                                  £1,310 - £2,453 / week

                                                                                  Book View

                                                                                  from £331 / 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

                                                                                  King's Cottage, perfect for Cheltenham & Cotswolds
                                                                                  Lovely Cheltenham House

                                                                                  Great location. Attached to good pub with excellent food and drink. A bit squashed for 6 adults, but very comfortable and clean. … see more
                                                                                  Hazleford Cottage
                                                                                  Hazelford Cottage

                                                                                  Great location, very clean and had everything you need. Marcie was very welcoming. Would stay again. … see more
                                                                                  Light and Bright Modern Cheltenham Home
                                                                                  Pleasant stay

                                                                                  The house we stayed at was nicely furnished, all beds very comfortable, nice kitchen area with complimentary food which was very nice but unfortunately it was adviertised as having a washing machine, we couldn’t find it but as we didn’t need it not a problem for us but if we were staying longer it could have been. The front door handle and lock broke, Jason was very quick to mend, he was aware that the shower door was also faulty but unfortunately no note to let us know that.see more
                                                                                  Coach House (Hawling)
                                                                                  Peace and quiet in the Cotswolds

                                                                                  The Coach House in Hawling was such a peaceful place to stay. Set in the grounds of the Old Rectory (yet with personal seclusion), the outlook was over fields and trees. Total silence and darkness for star gazing at night - the Milky Way was unobscured by light pollution. The cottage itself was full of charm and character, whilst decorated to a high quality. The welcome hamper was a nice touch. Easily accessible to the Slaughters, Winchcombe, Cheltenham, Stow and Bourton on the Water. Would definitely recommend.see more
                                                                                  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

                                                                                  Also consider