Villas and Holiday homes in Cheltenham

402 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Cheltenham villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

402 Villa rentals in Cheltenham

Best Cheltenham villas and holiday homes with a pool

Among the 402 accommodations in Cheltenham, here are the 4 best villas and holiday homes with a pool

Stunning Country House With A Swimming Pool, Hot Tub And Sauna In The Cotswolds - Keepers House - Cheltenham
Cheltenham
07/08 – 09/08
SG$4639/nighttotal: SG$9278 (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.
Finest Retreats - The Half-arc Of Painswick - Cheltenham
9.9 38 reviews
Cheltenham
07/08 – 09/08
SG$6240/nighttotal: SG$12480 (2 )

Finest Retreats - The Half-arc Of 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.
Luxury Cabin With Hot-tub & Cold Plunge! - Cheltenham
8.6 54 reviews
Cheltenham
17/07 – 31/07
SG$265/nighttotal: SG$3710 (14 )

Luxury Cabin With Hot-tub & Cold Plunge!

1 1
cabin , Cheltenham
This luxury cabin with a hot tub is located 45km from Coughton Court in Cheltenham, close to Kingsholm Stadium (14km) and Cotswold Water Park (35km). The accommodation has received excellent user ratings for cleanliness and location, making it a great choice for travellers seeking a comfortable and convenient stay.
The cabin offers 24 square meters of space and can accommodate up to 2 guests. You'll find a fully equipped kitchen, a private terrace, and a hot tub, perfect for relaxing after exploring the area.
The Landers - Cheltenham
9.1 31 reviews
Cheltenham
26/10 – 29/10
SG$1170/nighttotal: SG$3510 (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.

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

Spring House - Cheltenham
Cheltenham
26/10 – 29/10
SG$1362/nighttotal: SG$4086 (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.
Sandford House - Townhouse In Regency Cheltenham, Sleeps 8 - Cheltenham
Cheltenham
27/07 – 02/08
SG$717/nighttotal: SG$4302 (6 )

Sandford House - Townhouse In Regency Cheltenham, Sleeps 8

4 1
cottage , Cheltenham
Sandford House, a spacious 160 square meter cottage in Cheltenham, is centrally located within the Regency spa town, offering easy access to attractions such as Cineworld Cheltenham and Parabola Arts Centre.
This family-friendly property accommodates eight guests with four bedrooms, four bathrooms, a well-equipped kitchen featuring a dishwasher, and a south-facing garden with seating, ideal for al fresco dining and BBQs.
* Huge Wow Factor Central Cheltenham Abode * - Cheltenham
9.9 354 reviews
Cheltenham
27/07 – 02/08
SG$249/nighttotal: SG$1494 (6 )

* Huge Wow Factor Central Cheltenham Abode *

1 1
house , Gloucestershire
This stylish red-brick house is perfectly situated in the heart of Cheltenham, just a short walk from the town's shops, cafes, bars, and restaurants. It has received excellent ratings for location, cleanliness, and overall user experience.
The property offers two double bedrooms, both with king-size beds, and additional sleeping arrangements in the living area, accommodating up to eight guests. The house also provides permit parking, a modern open-plan kitchen/living/dining area with a pool table, and all bedding and towels are included.
Rosebay Gardens, Cheltenham - Delightful, Charming And Very Spacious 4br Retreat - Cheltenham
10 3 reviews
Cheltenham
27/08 – 30/08
SG$385/nighttotal: SG$1155 (3 )

Rosebay Gardens, Cheltenham - Delightful, Charming And Very Spacious 4br Retreat

4 2
house , Golden Valley
Rosebay Gardens is a 4-bedroom house in Golden Valley, located 11.9 kilometres from Kingsholm Stadium and 12.1 kilometres from Gloucester Cathedral.
This property offers accommodation for 13 guests with 2 bathrooms, a fully equipped kitchen, free WiFi, and private parking, plus a terrace for outdoor relaxation.

Frequently asked questions about villa rentals in Cheltenham

  • What are the must-see attractions in Cheltenham?

    Cheltenham has a lot to offer! You can't miss the beautiful architecture of the Montpellier district, a stroll through the Pittville Park, or a visit to the Cheltenham Art Gallery & Museum. The Everyman Theatre is also a must-see for theatre lovers.
  • What are the best villa rentals in Cheltenham?

    Among the villa rentals in Cheltenham, Tewkesbury Town House, Cotswold77 - Heart Of The Cotswolds and Apple Tree Cottage - 2 Bedroom (Double & King Beds) are the most popular ones.

  • What indoor activities for families are available in Cheltenham on rainy days?

    On a rainy day, head to the 'The Wilson' museum. It's a fantastic place for families with exhibits on natural history and local culture. The 'The Brewery Quarter' also has a cinema and bowling alley, perfect for a family day out.
  • What are the best villa rentals with a pool in Cheltenham?

  • What are the best activities in Cheltenham?

    Cheltenham has something for everyone. For those who enjoy the outdoors, a walk along the Cotswold Way is a must. If you prefer something more cultural, the Cheltenham Jazz Festival is a highlight of the year. For a day of shopping, the Montpellier district is the place to be.
  • What are the best villa rentals with a jacuzzi in Cheltenham?

  • What are the advantages of renting a house or a villa in Cheltenham

    Renting a house or villa gives you more space and privacy compared to a hotel. You can cook your own meals, relax in your own garden, and enjoy a more independent experience. There are some lovely properties in the Montpellier and Leckhampton areas.
  • What are the best villa rentals for families and kids in Cheltenham?

  • What food festivals or culinary events take place in and around Cheltenham?

    The Cheltenham Food & Drink Festival is a big event in the town, showcasing local produce and regional cuisine. You can also check out the 'Taste of Cheltenham' event, which brings together food and drink from across the region.
  • What are the best pet friendly villa rentals in Cheltenham?

  • What exclusive experiences are available when visiting Cheltenham?

    For a unique experience, you can enjoy a private tour of the Cheltenham Racecourse, home to the Cheltenham Festival. You can also visit the 'The Holst Birthplace Museum' for a glimpse into the life of the famous composer.
  • What are the best villa rentals with parking in Cheltenham?

  • Which part of Cheltenham would be ideal for a villa rental?

    The Montpellier and Leckhampton areas are popular choices for villa rentals. They offer a mix of quiet residential streets and easy access to the town centre and local amenities.

Destinations nearby

Best Cheltenham villas and holiday homes with parking

The Mitre, Cheltenham, Stylish, Sleeps 8, Parking, Central - Cheltenham
9.7 8 reviews
Cheltenham
30/12 – 01/01
SG$1108/nighttotal: SG$2216 (2 )

The Mitre, Cheltenham, Stylish, Sleeps 8, Parking, Central

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.
Brookbank Close By Signature Stays - Central - Parking - Racecourse - Cheltenham
8.3 3 reviews
Cheltenham
15/08 – 21/08
SG$380/nighttotal: SG$2280 (6 )

Brookbank Close By Signature Stays - Central - Parking - Racecourse

4 1
house , Cheltenham
New Brookbank House, a recently renovated holiday home in Cheltenham, is situated 13.5 km from Kingsholm Stadium and offers easy access to the Cotswolds Water Park (34 km away).
This spacious four-bedroom, three-bathroom property boasts 125 square metres of living space, sleeps up to 15 guests, and includes free Wi-Fi, private parking, and a fully equipped kitchen.
Two Double Bedrooms Guest Annexe With Ev Charging - Cheltenham
9.9 121 reviews
Cheltenham
21/07 – 24/07
SG$254/nighttotal: SG$762 (3 )

Two Double Bedrooms Guest Annexe With Ev Charging

1 2
house , Gloucestershire
This Cheltenham guest annexe is situated less than 100 metres from Cheltenham Race Course and a 10-minute walk (approximately 0.8 km) from Cheltenham town centre, offering easy access to shops, restaurants, and attractions.
This self-contained property boasts two double bedrooms, accommodating up to four guests, and includes a fully equipped kitchen, garden, fitness centre, secure parking, EV charging (surcharge applies), and bike storage; access to laundry facilities and a home gym is also available (subject to availability).
Stunning Townhouse With Large Garden - Sleeps 8! - Cheltenham
8.9 31 reviews
Cheltenham
27/08 – 30/08
SG$601/nighttotal: SG$1803 (3 )

Stunning Townhouse With Large Garden - Sleeps 8!

3 4
house , Cheltenham
This 3-bedroom house is situated in Cheltenham, just 800 metres from the University of Gloucestershire and 1.4 kilometres from Cheltenham Town Hall. It has received excellent ratings for location, cleanliness, and user experience.
The property offers 200 square metres of space and comfortably accommodates up to 8 guests. It features a fully equipped kitchen, a private terrace, a large garden, and free Wi-Fi, making it perfect for a relaxing and enjoyable stay.

Best Cheltenham villas and holiday homes with a garden

Self Contained Annex Adjoining A Family Home. - Cheltenham
9.9 92 reviews
Cheltenham
03/07 – 04/07
SG$153/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.
Spacious 3-bed Period Home Near Bath Road - Cheltenham
10 1 review
Cheltenham
15/08 – 29/08
SG$353/nighttotal: SG$4942 (14 )

Spacious 3-bed Period Home Near Bath Road

3 1
house , Cheltenham
This 3-bedroom period property in Cheltenham is located 8.3 kilometres from Gloucester Cathedral and 8.5 kilometres from Kingsholm Stadium, with further attractions such as Cotswold Water Park 19 kilometres away.
This 83 square meter house offers accommodation for up to 11 guests, featuring a fully equipped kitchen with a dishwasher and microwave, a garden, and complimentary WiFi.
Pinewood Walk By Signature Stays - Parking - Townhouse - Cheltenham
10 1 review
Cheltenham
11/09 – 13/09
SG$622/nighttotal: SG$1244 (2 )

Pinewood Walk By Signature Stays - Parking - Townhouse

4 6
house , Gloucestershire
This Gloucestershire holiday home, situated 10.5km from Kingsholm Stadium and 11.6km from Gloucester Cathedral, offers easy access to Gloucestershire's attractions.
The 110 square metre property boasts four bedrooms, three bathrooms, sleeps seventeen guests, includes a fully equipped kitchen, private garden, tennis court, free Wi-Fi and parking, and is suitable for families and groups.
Woodland Cabin | Cotswold Way | Logs & Dogs! - Cheltenham
10 56 reviews
Cheltenham
10/07 – 11/07
SG$350/nightfor 1 night

Woodland Cabin | Cotswold Way | Logs & Dogs!

1 2
cabin , Shurdington
This Shurdington studio offers direct access to the Cotswold Way for hiking and is an 8-minute drive from Cheltenham's Montpellier and Promenade areas, situated on a quiet road with a unique historical atmosphere from its past as a 1970s Prog Rock band's creative hub.
This dog-friendly apartment sleeps four guests and features a fitted kitchen with a gas hob and air fryer, private patio with a log burner, and access to adjoining woodland, with excellent WiFi provided.
©2026 cozycozy.com