Villas and Holiday homes in Cheltenham

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Cheltenham holiday homes
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402 Villa rentals in Cheltenham

Handpicked Holiday Houses with a Swimming Pool in Cheltenham

Enjoy a swim whenever you like, as these holiday homes in Cheltenham feature excellent on-site pool facilities.

Stunning Country House With A Swimming Pool, Hot Tub And Sauna In The Cotswolds - Keepers House - Cheltenham
Cheltenham
07/08 – 09/08
£2693/nighttotal: Â£5386 (2 )

Stunning Country House With A Swimming Pool, Hot Tub And Sauna In The Cotswolds - Keepers House

4 3
cottage , Cranham
Keepers House, a four-bedroom holiday home near Cranham and Birdlip in Gloucestershire, offers easy access to the Cotswolds Area of Outstanding Natural Beauty.
This pet-friendly property sleeps nine, boasting a heated swimming pool (additional charge Oct-Feb), extensive grounds with a pool house and outdoor games, a 16-seater dining room, cinema room with log burner, and modern amenities including a Smart TV and Sonos speaker.
The Landers - Cheltenham
9.1 31 reviews
Cheltenham
26/10 – 29/10
£679/nighttotal: Â£2037 (3 )

The Landers

5 10
house , Cheltenham
The Landers is a spacious house located in Cheltenham, just a short drive from Kingsholm Stadium and Gloucester Cathedral. This property has received excellent ratings for its location, cleanliness, and overall experience.
The house offers 5 bedrooms and 2 bathrooms, spanning 274 square metres, comfortably accommodating up to 10 guests. Guests can enjoy a private pool, a jacuzzi, a terrace, a garden, and a fully equipped kitchen, making it an ideal choice for families or groups looking for a relaxing and enjoyable stay.
Finest Retreats - Arc Painswick - Cheltenham
9.9 38 reviews
Cheltenham
07/08 – 09/08
£3623/nighttotal: Â£7246 (2 )

Finest Retreats - Arc Painswick

9 3
house , Painswick
ARC Painswick is a large holiday home located in the picturesque town of Painswick, just 11km from Kingsholm Stadium and 34km from Cotswold Water Park. The property has received excellent ratings for user experience, location, and cleanliness.
This spacious 9-bedroom, 10-bathroom property spans 600 square metres and provides plenty of space for large groups or families. Guests can enjoy a range of amenities, including a swimming pool, terrace, garden, spa, bar, and concierge service, as well as activities such as darts, cycling, and hiking in the surrounding area.
600 M² House ∙ 9 Bedrooms ∙ 24 Guests - Cheltenham
9.8 25 reviews
Cheltenham
07/08 – 09/08
£3623/nighttotal: Â£7246 (2 )

600 M² House ∙ 9 Bedrooms ∙ 24 Guests

9 3
house , Painswick
This nine-bedroom house is located in Painswick, a picturesque village in the Cotswolds, just a short distance from the town centre and within easy reach of Painswick Beacon.
The 600 square metre property features a private swimming pool, a fully equipped kitchen, and a spacious garden, ideal for large families or groups of friends looking for a relaxing retreat in the Cotswolds.

Best family friendly Cheltenham villas and holiday home

Among the 402 accommodations in Cheltenham, here are the 4 best family friendly villas and holiday homes

Charming Historic Cotswold Cottage In Central Winchcombe - Cheltenham
9.5 120 reviews
Cheltenham
07/08 – 09/08
£392/nighttotal: Â£784 (2 )

Charming Historic Cotswold Cottage In Central Winchcombe

2 3
house , Winchcombe
This charming 19th-century Cotswold cottage is located in Winchcombe, a picturesque town in the Cotswolds, just 15 miles from Gloucester's Kingsholm Stadium and 23 miles from Stratford-upon-Avon's Royal Shakespeare Theatre. The property enjoys excellent ratings for its location, cleanliness, and overall experience.
The cottage features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Enjoy modern amenities like a dishwasher, washing machine, and free Wi-Fi, and explore the beautiful Cotswolds by bike, fishing in nearby rivers, or visiting local attractions like Sudeley Castle and the Cotswold Way National Trail.
Spring House - Cheltenham
Cheltenham
26/10 – 29/10
£791/nighttotal: Â£2373 (3 )

Spring House

6 10
house , Brimpsfield
Spring House, situated in Brimpsfield, Gloucestershire, is 16km from Kingsholm Stadium and 24km from the Cotswold Water Park.
This six-bedroom property boasts 373 square metres of living space, offering a spacious layout with two living rooms, four bathrooms, and sleeps up to 21 guests, complete with a fully equipped kitchen, private patio, garden, parking, and Wi-Fi.
Elysian Heights - Five Bedroom Villa, Sleeps 10 - Cheltenham
Cheltenham
26/06 – 28/06
£1877/nighttotal: Â£3754 (2 )

Elysian Heights - Five Bedroom Villa, Sleeps 10

5 2
house , Cheltenham
Elysian Heights, a 5-bedroom detached house in Leckhampton Hill, Gloucestershire, offers panoramic Cotswolds views and is located approximately 2.5 kilometers from Cheltenham's cultural attractions including the Cheltenham Town Hall and Statue of Edward Wilson, with Cineworld Cheltenham and Cleeve Hill Golf Club within easy reach.
This family-friendly property accommodates up to 10 guests and features a cinema room, hot tub, indoor sauna, a garden with a children's playground and outdoor kitchen, plus parking for six cars.
Stylish 3-bed Gloucester House With Free Driveway Parking For 2 Cars - Cheltenham
8.4 5 reviews
Cheltenham
07/08 – 09/08
£278/nighttotal: Â£556 (2 )

Stylish 3-bed Gloucester House With Free Driveway Parking For 2 Cars

3 3
house , Gloucester
This Gloucestershire house, situated 2.4km from Kingsholm Stadium and 2.7km from Gloucester Cathedral, offers easy access to Gloucester's attractions and the Cotswold Water Park (38.6km away).
The 75 square metre property sleeps eight guests in three bedrooms with three bathrooms, boasting a fully equipped kitchen, private parking, and a garden; perfect for families or groups exploring Gloucestershire.

Frequently asked questions about villa rentals in Cheltenham

Destinations nearby

Best Cheltenham villas and holiday homes with parking

Stylish Two Bed Cheltenham Retreat With Hot Tub - Cheltenham
Cheltenham
18/07 – 20/07
£244/nighttotal: Â£488 (2 )

Stylish Two Bed Cheltenham Retreat With Hot Tub

2 2
house , Cheltenham
This Cheltenham property is located 12.7 kilometres from Kingsholm Stadium, 12.7 kilometres from Sudeley Castle and 14.6 kilometres from Gloucester Cathedral.
This 2-bedroom cottage accommodates up to 7 guests and features a private hot tub, a fully equipped kitchen with a dishwasher, and free WiFi, with cycling opportunities nearby and a garden for relaxation.
Homely Regency Style House In The Heart Of Cheltenham - Cheltenham
9.9 15 reviews
Cheltenham
27/08 – 30/08
£270/nighttotal: Â£810 (3 )

Homely Regency Style House In The Heart Of Cheltenham

3 4
house , Cheltenham
This detached property in Cheltenham is located 15 kilometres from Kingsholm Stadium and 30.5 kilometres from Cotswold Water Park, offering a private entrance and a terrace.
This 116 square meter house accommodates up to 11 guests with three bedrooms, two bathrooms, a fully equipped kitchen, and complimentary WiFi, plus private parking.
Racecourse House 5br 3ba With Parking - Cheltenham
Cheltenham
06/08 – 08/08
£498/nighttotal: Â£996 (2 )

Racecourse House 5br 3ba With Parking

1 4
house , Cheltenham
This five-bedroom, three-bathroom property in Cheltenham offers proximity to the Racecourse and is situated within 12 kilometres of Sudeley Castle, Gloucester Cathedral, and Kingsholm Stadium.
This spacious accommodation provides complimentary WiFi, private parking, and a fully equipped kitchen, making it ideal for groups of up to 19 guests seeking a comfortable stay with easy access to local attractions.
Ivy Cottage, 1 Bedroom, Cheltenham City Centre By Mystayinn - Cheltenham
8.7 3 reviews
Cheltenham
21/07 – 24/07
£167/nighttotal: Â£501 (3 )

Ivy Cottage, 1 Bedroom, Cheltenham City Centre By Mystayinn

1 2
house , Cheltenham
This flat is located in Cheltenham City Centre, offering easy access to local amenities and attractions, with Gloucester Cathedral 12.4 kilometres away and Sudeley Castle 13.8 kilometres distant.
This 60 square metre property features one bedroom, two bathrooms, a kitchen equipped with a fridge, microwave, and dishwasher, and accommodates up to seven guests, with complimentary WiFi and private parking available.

Neighborhoods and points of interest in Cheltenham

Best Cheltenham villas and holiday homes with a garden

Cottage ∙ 3 Bedrooms ∙ 8 Guests - Cheltenham
Cheltenham
11/09 – 13/09
£250/nighttotal: Â£500 (2 )

Cottage ∙ 3 Bedrooms ∙ 8 Guests

3 6
cottage
This charming cottage is located on the edge of Cheltenham, within walking distance of the university grounds, pubs, and the town centre. The suburban setting provides a peaceful retreat while still being close to the action.
The cottage comfortably sleeps 8 guests in 4 bedrooms, making it ideal for families or groups of friends. It includes a well-equipped kitchen with a dishwasher, a private garden with a decking area and barbecue, and free Wi-Fi.
Self Contained Annex Adjoining A Family Home. - Cheltenham
9.9 92 reviews
Cheltenham
03/07 – 04/07
£89/nightfor 1 night

Self Contained Annex Adjoining A Family Home.

1 2
house , Gloucestershire
This self-contained one-bedroom annex near Cheltenham, Gloucestershire, is situated 2.4 kilometres from the M5 motorway and a 10-minute drive from Cheltenham town centre.
The property offers off-road parking, a private patio, secure bike storage (ideal for National Cycle Route 41 users), and sleeps two guests in a double bed, with a kitchenette and en-suite bathroom.
Vibrant 4br I 2 Bath I Entire Home I Ctr Cheltenham I Short And Long Term Stays I Relocations - Cheltenham
9.7 8 reviews
Cheltenham
11/09 – 18/09
£452/nighttotal: Â£3164 (7 )

Vibrant 4br I 2 Bath I Entire Home I Ctr Cheltenham I Short And Long Term Stays I Relocations

4 2
house , Cheltenham
This recently renovated four-bedroom house is located in Cheltenham, 13.6 kilometres from Kingsholm Stadium and 13.7 kilometres from Gloucester Cathedral.
This spacious 110 square metre property accommodates up to 15 guests with a fully equipped kitchen, free WiFi, and a terrace, offering a convenient base for exploring attractions such as Sudeley Castle, located 13 kilometres away.
Cheltenham-2 Bedroom Home-sleeps 6-parking-work Or Leisure - Cheltenham
8.5 45 reviews
Cheltenham
06/09 – 09/09
£334/nighttotal: Â£1002 (3 )

Cheltenham-2 Bedroom Home-sleeps 6-parking-work Or Leisure

2 2
house , Cheltenham
This Cheltenham house, situated approximately 13.8 kilometres from Kingsholm Stadium and 14.5 kilometres from Sudeley Castle, offers convenient access to local attractions.
The 93 square metre property sleeps up to six guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, private garden, free parking, and WiFi; a washing machine and baby safety gate are also provided.
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