List your home
Apply filters
£ to

34 Holiday homes in Cheltenham

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • England Clear
  • Central England/Cotswolds Clear
  • Gloucestershire Clear
  • Cheltenham Clear
  • All locations
  • Charlton Kings (1)
  • Fossebridge (1)
  • Leckhampton (1)
  • Montpellier suburb (16)
  • Pittville (5)
  • Prestbury (1)
  • Tivoli (1)

more +

less -

Also consider

Cornwall
2,983 properties
Greater London
941 properties
Cumbria / Lake District
940 properties
Devon
2,810 properties
Central England / Cotswolds
940 properties
Dorset
819 properties
Isle of Wight
507 properties
Peak District / Derbyshire
460 properties
Somerset
610 properties
Kent
557 properties
Sussex
770 properties
Norfolk
1,023 properties
Isle of Man
11 properties
Northumberland
640 properties
Yorkshire / Yorkshire Dales
1,496 properties
Coastal Cottages
222 properties
Central London/Zone 1
2,214 properties
Central London/Zone 2
1,154 properties
Newquay
613 properties
Bideford
492 properties

Filters applied: House (34)

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
34 Results  |  
16 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £76 /night

£530 - £1060 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Lying in the tiny hamlet of Deerhurst Walton, this is a converted, Grade II listed dovecote. Set in the grounds of the owner's 17th-century farm, this romantic 2 bed conversion has been lovingly converted into a 2 bedroom property with comfortable acco for upto 4 pax. Restaurants, pubs, supermarkets & take aways nearby On main bus route to Tewkesbury, Cheltenham & Gloucester  …see more

17 Photos

House | 5 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £318 /night

£2226 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
5 bedroom 4 receptions, detached house with 120 foot garden, parking for 5 cars and garage for 1 car  …see more

10 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £145 /night

£1013 - £3795 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
Sheldon Court is a three bedroom house able to comfortably sleep up to six adults. It has two en-suites, a family bathroom, & a downstairs toilet. This Cheltenham serviced house is styled with gorgeous antique furnishings which bring a great sense of character  …see more

Featured properties

20 Photos

House | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

4 Nights min stay

Add to shortlist

from £72 /night

£499 - £631 / week

View

Key info:

  • Nearest beach 100 km
  • Suitable for children over
  • Car not necessary
  • No pets allowed
  • Private garden
The main bedroom incorporates a super king size double bed, the 2nd has two singles. The house is an average size 2 story 1970's build. Pleasant front & rear garden / patio area with parking close to the front door. Bathroom incorporates a bath, shower Quiet location, walking distance to Cheltenham town & Montpellier. Festivals, shops, restaurants, parks.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

Good 3/5 

Short stays welcome

Add to shortlist

from £78 /night

£540 - £980 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
situated in one of england’s most unspoilt and picturesque villages this recently refurbished detached honey coloured stone house is situated in the heart of the village offering luxury accommodation, with its own large garden and private parking. upper slaughter is a peaceful village and is a wonderful base from which to explore the cotswolds, being close to the historic market towns of stow-on-the-wold, bourton-on-the-water, moreton-in-marsh, broadway and burford and many quintessential limestone villages. The building that dominates the village is a beautiful manor house which is now a hotel with a michelin star restaurant for those special occasions. There's fantastic walks right from the doorstep and the sister village of lower slaughter is a short stroll away. the refurbished accommodation retains all its original charm and character, is arranged over three floors and offers three bedrooms: on the second floor, 1 master double and 1 single with a pull-out single that can be made into a twin or double on request with en-suite shower. On the third attic floor, with sloping ceiling and open staircase with stair-gate, 1 single with a pull-out single that can be made into a twin. Shower room: on the second floor, with wc. The ground floor has a separate wc off the utility room. Lounge: with feature original stone fireplace with woodburner, smart tv with dvd. Kitchen/diner: with cooker, fridge/freezer, dishwasher and microwave. Utility: with washing machine and tumble dryer. conservatory: overlooking the 1 acre (approximately) of landscaped garden with seating. Outside: enclosed garden and patio area with seating. Amenities: parking for 4 cars. Bed linen, towels, electric, central heating and wi-fi included. Regret no smoking or pets. additional info: short breaks charged at 3 nights 80%, 4 nights 80% and 5 nights 90% of the full weekly cost. Location: shops in bourton-on-the-water 3 miles and restaurant walking distance.  …see more

18 Photos

House | 1 Bedroom | sleeps 2

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £72 /night

£500 - £1000 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Cotswold stone two-storey coach house, totally restored and extended. Small but beautifully formed one double-bedroomed hideaway for couples. All amenities of Bath road market and shops on the doorstep, Montpellier and the Promenade a fifteen minute stroll away. All newly fitted and fully equipped with high quality fixtures, furnishings and accessories.  …see more

24 Photos

House | 5 Bedrooms | sleeps 9

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £358 /night

£2500 - £6000 / week

View

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

House | 2 Bedrooms | sleeps 4

Good 3.5/5 

3 Nights min stay

Add to shortlist

from £72 /night

£500 - £1000 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
No 17 is a welcoming town house offering high standards of accommodation in one double and one with 4 foot bed. Ideal location and off-road allocated parking. Includes kitchen, microwave, washing machine, TV, DVD, CD, broadband, garden, bedding & towels.  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £158 /night

£1100 - £2736 / week

View

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

24 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £228 /night

£1590 - £3710 / week

View

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

9 Photos

House | 2 Bedrooms | sleeps 4

Good 3/5 

7 Nights min stay

Add to shortlist

from £49 /night

£340 - £650 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Walking distance to the Cheltenham Racecourse - Zip & link beds for 2 x twin bedrooms, or 2 x king size bedrooms- Mod cons - TV with Freeview & DVD player, CD player, WiFi, dishwasher & washer / dryer - Off street parking.  …see more

10 Photos

House | 2 Bedrooms | sleeps 3

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £57 /night

£395 - £1000 / week

View

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

12 Photos

House | 3 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £72 /night

£500 - £1000 / week

View

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

11 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £86 /night

£600 - £1500 / week

View

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

13 Photos

House | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £72 /night

£500 - £1500 / week

View

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

Add to shortlist

from £143 /night

£1000 - £3000 / week

View

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

14 Photos

House | 4 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £86 /night

£600 - £1600 / week

View

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

18 Photos

House | 5 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £115 /night

£800 - £3500 / week

View

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

8 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £47 /night

£329 - £764 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This detached holiday bungalow is situated in the elevated village of Birdlip, centrally located for exploring the many delights of the Cotswolds. Close by is the Cotswold Way, offering walks and wonderful views. Regency Cheltenham, 6 miles, has boutique shopping, th...  …see more

6 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £49 /night

£337 - £2197 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This raised ground floor, modern holiday apartment is ideally situated within walking distance of Regency Cheltenham and easy reach of the racecourse. There are many well-renowned festivals and pretty, honey-coloured, Cotswold stone towns and villages nearby such as ...  …see more

8 Photos

House | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £37 /night

£256 - £530 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Situated just outside the beautiful Cotswold market town of Winchcombe, Stable Yard Cottages are a group of three well presented holiday cottages and a studio apartment, in a peaceful location. Ideally placed for touring the Cotswolds and the many picturesque towns a...  …see more

8 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £44 /night

£303 - £593 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This former cider house is located in the grounds of the owner's 12th century manor house. Quietly positioned in the countryside, a short driving distance from the Regency town of Cheltenham. The detached holiday cottage is well appointed and retains much of its orig...  …see more

12 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £68 /night

£474 - £986 / week

View

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

17 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £46 /night

£319 - £1095 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Located at the end of a 2 mile track, these two holiday cottages (refs 28367 and 28368) offer a truly secluded setting with far-reaching views and are adjacent to the owner's home. Needlehole Cottages are situated close to the small Cotswold parish of Coberley, an Ar...  …see more

15 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £69 /night

£477 - £879 / week

View

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

6 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £57 /night

£398 - £738 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Set in glorious countryside with outstanding views towards the Cotswold Hills and Malverns, in quiet rural surroundings, this beautifully appointed barn conversion (attached to the owners' home) is just a few miles from the market town of Winchcombe and elegant Regen...  …see more

9 Photos

House | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £38 /night

£265 - £607 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Situated just outside the beautiful Cotswold market town of Winchcombe, Stable Yard Cottages are a group of three well presented holiday cottages and a studio apartment, in a peaceful location. Ideally placed for touring the Cotswolds and the many picturesque towns a...  …see more

13 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £54 /night

£377 - £865 / week

View

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

11 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £36 /night

£246 - £712 / week

View

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

8 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £38 /night

£261 - £558 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Set within the Cotswold countryside, with outstanding views towards Dumbleton Hill and the Malverns, this delightful barn conversion, adjacent to the owners' home, is a perfect holiday location. The property is situated just a few miles from the market town of Winchc...  …see more

7 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £52 /night

£359 - £865 / week

View

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

10 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £50 /night

£344 - £784 / week

View

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

7 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £39 /night

£271 - £567 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Situated in the thriving Cotswold town of Winchcombe, Barley Cottage is in the perfect location, on a main road, for exploring the Cotswolds, with a choice of pubs plus a well respected Michelin-starred restaurant just a few doors away. Leave the car behind to stroll...  …see more

13 Photos

House | 12 Bedrooms | sleeps 20

3 Nights min stay

Add to shortlist

from £3143 /night

£22000 / week

View

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