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102 Holiday homes in Cheltenham

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102 Results  |  
8 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

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from £86 /night

£601 - £1833 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Charming one bedroomed duplex within an easy walk of the centre of town. With its own private garden and dedicated off street parking, this is the perfect location for being near the centre of things without the hustle and bustle or mid town life.  …see more

20 Photos

Barn | 4 Bedrooms | sleeps 8

Excellent 5/5 

1 night min stay

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from £58 /night

£400 - £1850 / week

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Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
A conversion of five traditional cart barns, in the village of Compton Abdale. 5* Gold Award Winner, the barn is light, airy, open plan, especially suitable for those with limited mobility as two of the four bedrooms and a bathroom are on the ground floor.  …see more

20 Photos

Cottage | 4 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

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from £115 /night

£800 - £1600 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Family/group accommodation. Rural idyll yet "civilisation" on doorstep. Only 12 minutes by car from Cheltenham town centre. Easy reach of all Cotwold tourist attractions - London 2.5 hrs. Birmingham centre only 1.25 hours by car and day trip to Wales easily possible. Looking for Cheltenham race week? View the finishing post (2.5 miles) from the terrace. Transport arranged.  …see more

Featured properties

24 Photos

Apartment | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £65 /night

£450 - £1850 / week

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Key info:

  • Nearest beach 35 km
  • Suitable for children over
  • Car not necessary
  • No pets allowed
Tripadvisor "Certificate of Excellence 2014"Cheltenham`s No1 holiday rental on Tripadvisor."Affordable Quality" Great Service. Self catering holiday apartment 3 bedrooms,2 bathrooms,inviting lounge,large kitchen.Onsite off road parking,wifi,Close to the race course. Classic modern home,with comfortable quality furnishings, wifi, Parking off road for two cars if required.  …see more

14 Photos

Cottage | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £58 /night

£400 - £1850 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
History abounds in The Guggle. Originally built in around 1600, it became the Horse and Groom Public House in 1700 and oozes period features, with crookedy walls and ceilings, wooden beams and original 17th Century wall painting.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 3

Excellent 5/5 

3 Nights min stay

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from £38 /night

£260 - £380 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
SO CONVENIENT FOR ALL AREAS OF CHELTENHAM. OVERLOOKS SANDFORD PARK.. VERY CLOSE TO FESTIVALS THEATRE, TOWN HALL, SHOPS, PARKS, RACING, RESTAURANTS. I WILL NEVER PUT PRICES UP IN SCHOOL SUMMER HOLIDAYS. I BELIEVE IT IS UNFAIR TO PEOPLE WITH CHILDREN AND PEOPLE WITHOUT. Very competitive pricing doesn't mean cleanliness & homeliness aren't important.THEY ARE UTMOST IMPORTANCE!!  …see more

13 Photos

Barn | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £79 /night

£550 - £700 / week

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Key info:

  • Suitable for children over
  • Car essential
  • No pets allowed
  • Private garden
Charming stone barn in idyllic rural location with beautiful views. Ideal for exploring the Cotswolds and it's wealth of historic houses and prestigious gardens, literary and musical festivals, excellent shopping and restaurants and horse racing at Cheltenham.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £228 /night

£1590 - £3710 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
A cut above the rest - spacious luxury Coach House tucked away in a private setting in the grounds of a classic Regency Villa in the upmarket leafy area of Pittville. Ten minutes walk from the centre of Cheltenham and the Racecourse. Well furnished with quality bedding. Sleeps six in three bedrooms with two King Size beds and two Single beds or other combinations as required.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

2 Nights min stay

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from £106 /night

£737 - £1908 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
This spacious one bedroom apartment with off road parking is close to the stylish area of Montpellier and Gloucester is also an easy commute. There are even buses which stop just a minutes' walk from here, to take you into Cheltenham town centre, Gloucester or Cleeve, Free wi fi, weekly cleans, weekly linen change, and off road parking are included in this stay. * Rates are  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £79 /night

£550 - £700 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
4* Regency elegance with a unique theatrical atmosphere close to Cheltenham town centre with off-street parking.  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 2

Very Good 4.5/5 

1 night min stay

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from £65 /night

£450 / week

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Key info:

  • Nearest beach 100 km
  • Not suitable for children
  • Car not necessary
  • No pets allowed
This self-catering apartment is in the centre of the Regency Montpellier district of Cheltenham, within easy walking distance of the main Festival venues and the best restaurants. It is an ideal location for a relaxing weekend or a longer term stay of up to 31 days.  …see more

24 Photos

Converted Chapel | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

2 Nights min stay

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from £69 /night

£482 - £1071 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
The Old Chapel is a beautiful, Grade II listed, detached stone chapel, moments from the centre of the village of Northleach, in the heart of the Cotswolds. With impressive arches, stained glass windows and vaulted ceilings, the property has an abundance of character. SPECIAL OFFERS: LATE BOOKING DISCOUNTS & EARLY BIRD DEALS!  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

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from £158 /night

£1100 - £2736 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Lakeside House is a beautiful Grade II listed property, set in a private location within the grounds of The Inn at Fossebridge, in the heart of the Cotswold countryside. Guests have access to all the Inn's services, including its cosy bar and private dining facilities. SPECIAL OFFERS: LATE DEALS!  …see more

23 Photos

Cottage | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £77 /night

£535 - £1190 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Stable Cottage is a beautiful, grade II listed building, formerly the stables for the neighbouring coaching inn. The Cotswold stone stables have been lovingly renovated, to create a warm, character filled cottage, perfectly located in the heart of the Cotswolds. SPECIAL OFFERS: LATE BOOKING DISCOUNTS!  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £136 /night

£950 - £1500 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
two bedroom apartment, cheltenham, montpellier, self catering, cheltenham festivals, regency house  …see more

24 Photos

House | 5 Bedrooms | sleeps 9

Excellent 5/5 

2 Nights min stay

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from £358 /night

£2500 - £6000 / week

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Key info:

  • Suitable for children over
  • Some pets are welcome - please contact the owner
  • Private garden
Self catering house in Cheltenham, private dining, wedding venue, wedding reception, venue hire, private chef, Montpellier. Serviced house in Cheltenham. Five star rating. Self catering house in Cheltenham, private dining, wedding venue, wedding reception, venue hire, private che  …see more

7 Photos

Apartment | 2 Bedrooms | sleeps 3

Excellent 5/5 

3 Nights min stay

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from £43 /night

£300 - £1500 / week

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Key info:

  • Suitable for children over
  • Car not necessary
  • No pets allowed
A quiet 2 bedroom 2 bathroom gem conveniently situated between Imperial Gardens and Montpellier Gardens for those wanting to stroll to the various Festivals held in Montpellier.  …see more

8 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £85 /night

£595 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Cheltenham S/C holiday apartment with parking and a garden.  …see more

13 Photos

Apartment | 3 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £86 /night

£600 - £825 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Self-catering Cheltenham town centre apartment within quiet cul de sac. Flexible light and airy accommodation in ideal location for single groups or couples visiting the town without the need for a car. Adjacent apartment sleeps another 6 people for large groups!  …see more

14 Photos

Apartment | 3 Bedrooms | sleeps 6

Good 3/5 

4 Nights min stay

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from £75 /night

£525 - £1200 / week

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Key info:

  • Suitable for children over
  • Car not necessary
  • No pets allowed
Stylish town centre Cheltenham apartment suitable for couples with older children or singles. Ideal for all town centre events or those re-locating. 5 mins walk from Cheltenham railway station. A perfect base for exploring the Cotswolds. . This light and airy apartment has everything you need for a longer stay if you are between houses  …see more

11 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £86 /night

£600 - £1500 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self-catering house sleeps up to 6. Ideal for Greenbelt, The Literature Festival, Paddy Power and Gold Cup race meetings and exploring the Cotswolds. A sunny rear garden has a BBQ and parking for 2 cars. FREE WiFi.  …see more

12 Photos

House | 3 Bedrooms | sleeps 4

4 Nights min stay

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from £72 /night

£500 - £1000 / week

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Key info:

  • Suitable for children over
  • Car not necessary
  • No pets allowed
  • Private garden
Self-catering budget town centre dormer bungalow with downstairs twin or double bedroom, bathroom, sitting room and kitchen for those who cannot manage stairs. A bonus of 2 further bedrooms upstairs for larger groups. Off road parking & private garden.  …see more

12 Photos

Chalet | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

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from £50 /night

£350 - £600 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Self-catering chalet on the Cotswold Way. Ideally situated for walkers and cyclists exploring the area, yet close to Cheltenham town.  …see more

18 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

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from £115 /night

£800 - £3500 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self-catering gem offering 5 bedrooms and 4 bathroooms less than 10 mins walk from Cheltenham racecourse, The Pittville Pump rooms and Cheltenham Leisure centre. Ideal for sedate HEN nights, family reunions and work colleagues travelling together.  …see more

14 Photos

House | 4 Bedrooms | sleeps 6

2 Nights min stay

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from £86 /night

£600 - £1600 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
A Self-Catering town centre house with 4 bedrooms and 6 single beds, perfect for business colleagues, groups of friends, tourists, or sedate hens. Ideal base for the Gold Cup, Literature Festival, University visits and touring the Cotswold villages. Garden & Free wifi  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

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from £67 /night

£465 - £575 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Beautiful two bedroomed apartment forming part of a Regency townhouse in the Pittville area of Cheltenham. Tastefully furnished and with its own private courtyard. Conveniently located for the famous Gold Cup, Pump Rooms, shopping, parks and Cheltenham's many festivals.  …see more

10 Photos

House | 2 Bedrooms | sleeps 3

Excellent 5/5 

2 Nights min stay

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from £57 /night

£395 - £1000 / week

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Key info:

  • Suitable for children over
  • Some pets are welcome - please contact the owner
  • Private garden
Stylish holiday mobile home sandwiched between Cheltenham and Winchcombe, in a rural village setting with a pub. This is a great area to start a tour of the Cotswold region.  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £72 /night

£500 - £1500 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Self-catering house offering 3 bedrooms with 5 beds, on the Western side of Cheltenham centre with easy M5 motorway access to Gloucester, Worcester & Tewkesbury. Great for professionals working in the area at GCHQ, Ultra Electronics, GEAviation, Spirax Sarco. FREE WIFI  …see more

11 Photos

House | 5 Bedrooms | sleeps 10

Very Good 4/5 

2 Nights min stay

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from £143 /night

£1000 - £3000 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
A 5 bedroom self-catering townhouse in Cheltenham centre, tastefully furnished to appeal to all ages and group sizes. Ideal as a base for exploring the Cotswolds, town centre Festivals, the Prestbury Park racecourse, Pittville Pump Rooms and The Everyman Theatre.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £121 /night

£843 / week

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Key info:

  • Suitable for children over
  • Car not necessary
  • No pets allowed
A perfectly positioned apartment in Fashionable Cheltenham, A nice and spacious 2 bedroomed apartment offering accommodation for up to 4 people, It has 2 bedrooms, dining room/ living room, kitchen and bathroom with P bath/ shower.  …see more

16 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

1 night min stay

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from £143 /night

£1000 - £2000 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
A light and spacious two bedroom apartment located in this Grade 2 listed landmark building and situated in the heart of Cheltenham within a moments stroll of The Promenade, Montpellier, Cheltenham Ladies college and all amenities. Free iSecure remote gated parking.  …see more

10 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £49 /night

£341 - £784 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Sheerwater is a three bedroom, single storey, semi-detached holiday bungalow, situated on the edge of Cheltenham in Bishop's Cleeve. It is the ideal location for race meetings (1 mile) and close to the pretty Cotswolds towns and villages, including Broadway, Stow-on-...  …see more

15 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £69 /night

£477 - £879 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This spacious detached barn, dating from 1650, adjacent to the owners' home in Winchcombe, is the perfect base for exploring the Cotswolds AONB. Stroll through the historic market town, walk to the famous Sudeley Castle, or ramble in rolling hills, including the Cots...  …see more

7 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £52 /night

£359 - £865 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Thrift Cottage is a thatched cottage at the centre of the village of Gotherington. Nestling under Prescott and Cleeve Hills it is ideally placed to explore the Cotswolds, Cheltenham Spa and Cheltenham Racecourse. There are tennis courts and a riding school within eas...  …see more

12 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £68 /night

£472 - £986 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Occupying a superb position with wonderful rural views, yet within a mile or so of Cheltenham's elegant town centre, these delightful holiday cottages have been created from a range of 19th-century barns and are furnished and equipped to high standards. All cottages ...  …see more

11 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £37 /night

£259 - £712 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated at Lower Stanley, in the peaceful village of Gretton, this is the ideal location to enjoy the local landscape. Perfect for walkers, there are numerous paths, bridleways and cycle paths from the door. The Lodge is attached to the owners' house but provides pr...  …see more

13 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £54 /night

£377 - £865 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The Casita offers the best of both worlds - a short walk to the fashionable shops and restaurants of Cheltenham's elegant Montpelier district, plus easy access to numerous Cotswold villages such as Winchcombe, Stow-on-the-Wold and Bourton-on-the-Water. Nestled in one...  …see more

4 Photos

Cottage | 2 Bedrooms | sleeps 4

Short stays welcome

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from £50 /night

£345 - £598 / week

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Key info:

  • Suitable for children over
  • No pets allowed
  • Private garden
This charming, semi-detached, stone cottage in Prestbury near Cheltenham can sleep up to four people in two bedrooms.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 3

1 night min stay

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from £90 /night

£630 - £800 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Stunning Apartment Are Contained Within This Beautiful Georgian Building. It Is Very Tastefully Decorated Whilst Still Retaining The Elegant Period Features Of The Property.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

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from £90 /night

£630 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
We have been able to achieve a four star gold accolade grading by the British Tourist Authority. This very contemporary one bed apartment.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

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from £90 /night

£630 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
We have been able to achieve a four star gold accolade grading by the British Tourist Authority. This very contemporary one bed apartment.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £115 /night

£800 - £900 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
These brand new Apartments are furnished to a very high standard, Tastefully Decorated Whilst Still Retaining The Elegant Period Features Of This Victorian Terrace Property. Ideal for groups, business or leisure stays.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

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from £115 /night

£800 - £900 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Stunning Apartment Are Contained Within This Beautiful Georgian Building. It Is Very Tastefully Decorated Whilst Still Retaining The Elegant Period Features Of The Property.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 5

1 night min stay

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from £115 /night

£800 - £900 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Stunning Apartment Are Contained Within This Beautiful Georgian Building. It Is Very Tastefully Decorated Whilst Still Retaining The Elegant Period Features Of The Property.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

Excellent 5/5 

1 night min stay

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from £100 /night

£700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
We have been able to achieve a four star gold accolade grading by the British Tourist Authority. This very contemporary one bed apartment.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

Good 3.5/5 

1 night min stay

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from £90 /night

£630 - £700 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
We have been able to achieve a four star gold accolade grading by the British Tourist Authority. This very contemporary one bed apartment.  …see more

13 Photos

House | 12 Bedrooms | sleeps 20

3 Nights min stay

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from £3143 /night

£22000 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
A beautiful Georgian/Jacobian House set within a 2000 acre estate in the Oxfordshire Cotswolds with formal and landscaped garden, canalized stream and several springs which act as the centre piece to the surrounding grounds, lakes and woodland and Norman Church.  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 4

Very Good 4.5/5 

1 night min stay

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from £58 /night

£400 / week

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Key info:

  • Nearest beach 90 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Our modern and comfortable garden apartment is family run and offers a home from home within walking distance of the town centre.  …see more

5 Photos

B&B | 1 Bedroom | sleeps 2

Min stay varies

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from £137 /night

£954 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Double super king size bed with en-suite shower room 5 minutes walk to racecourse Free private off road parking for 1 car Flat screen T.V. Free W.I.F.I. Full English breakfast included  …see more

9 Photos

Cottage | 3 Bedrooms | sleeps 6

Min stay varies

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from £137 /night

£953 - £1590 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Unique period house in Charlton Kings, Cheltenham - the core of it dating back to 14th Century - There is so much to do in the local area - festivals, RSC, Cotwolds all with in reach of this amazing cottage!  …see more