Best Holiday rentals and Airbnb offers in Cheltenham
9.0 12 reviews
Cheltenham
27/06 – 04/07
SG$262/nighttotal: SG$1834 (7 )
Contractor Friendly 3bed House Cheltenham
3 2
house , Cheltenham
This three-bedroom apartment is located in Cheltenham, just 13.7 kilometres from Kingsholm Stadium and 13.3 kilometres from Sudeley Castle. The surrounding area offers a peaceful and relaxing atmosphere, perfect for a family getaway. The property spans 127 square metres and comfortably accommodates up to six guests. It features a fully equipped kitchen, a private garden, free Wi-Fi, and a washing machine, ensuring a comfortable and convenient stay.
10 207 reviews
Cheltenham
30/06 – 03/07
SG$238/nighttotal: SG$714 (3 )
7 Diamond Jubilee, Cheltenham
1 2
apartment , Gloucestershire
Diamond Jubilee, a fully electric self-catering apartment in Cheltenham's Suffolks area, offers easy access to Montpellier's shops and restaurants, and is within walking distance of Cheltenham's many festivals. This recently renovated coach house features an open-plan layout over two levels, a king-size bedroom, a glass-walled en-suite shower room, and on-site parking (unsuitable for large vehicles), accommodating up to two guests.
9.7 28 reviews
Cheltenham
21/08 – 23/08
SG$386/nighttotal: SG$772 (2 )
King's Cottage, Cheltenham
3 4
apartment , Charlton Kings
King's Cottage is situated in Charlton Kings, a short walk from the Royal pub and a 2 km drive from the town of Cheltenham. The cottage, a former bakery dating back to 1830, sleeps 6 guests and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher.
8.4 8 reviews
Cheltenham
02/07 – 05/07
SG$322/nighttotal: SG$966 (3 )
Hermitage Cottage
3 3
house , Gloucestershire
Hermitage Cottage, a Gloucestershire holiday home, is conveniently located near Sudeley Castle (14.6 km), Kingsholm Stadium (14.2 km), and the Cotswold Water Park (32.2 km), offering easy access to these and other Gloucestershire attractions. This two-bedroom property boasts 50 square metres of floor space, including a fully equipped kitchen, private parking with an EV charging point, and sleeps up to seven guests; towels and bed linen are provided.
10 43 reviews
Cheltenham
30/06 – 03/07
SG$252/nighttotal: SG$756 (3 )
Town Centre Stay With Cozy Balcony Retreat
1 2
apartment , Gloucestershire
This Cheltenham apartment, ideally located within walking distance of Cheltenham's shops, restaurants, and parks, offers a central Gloucestershire base for exploring the area. The one-bedroom, two-bathroom flat sleeps four guests and boasts a fully equipped kitchen, a large balcony, and a 50" TV; nearby activities include exploring Pittville Park or visiting the Cheltenham Art Gallery & Museum.
9.7 386 reviews
Cheltenham
11/01 – 12/01
SG$141/nightfor 1 night
Modern Studio In The Heart Of Cheltenham
1 2
studio , Gloucestershire
This Cheltenham studio flat offers a central location, a 30-minute walk or 4.8-kilometre drive from Cheltenham Racecourse and close to numerous bars, cafes, and restaurants. The ground-floor apartment features secure bike storage, sleeps two guests, includes a fridge and microwave, and benefits from excellent user, location, and cleanliness ratings.
Cheltenham
02/07 – 05/07
SG$245/nighttotal: SG$735 (3 )
Stylish 2-bed Home Close To Cheltenham Town Centre
2 3
apartment , Cheltenham
This beautifully restored Victorian flat is located a short stroll from Cheltenham town centre, offering easy access to Cheltenham Town Hall and the Holst Birthplace Museum. This two-bedroom apartment accommodates four guests and features a private garden, a four-piece bathroom with a roll-top bath, and is equipped with a Smart TV, espresso coffee maker, and air fryer.
9.7 15 reviews
Cheltenham
30/06 – 03/07
SG$189/nighttotal: SG$567 (3 )
‘Tivoli’ Stylish Apartment In Suffolks Cheltenham
1 2
apartment , Gloucestershire
This Cheltenham apartment, situated in the Suffolks area, is a short walk from Montpellier Gardens and the town centre. The ground-floor flat offers a spacious open-plan kitchen and lounge, one king-size bedroom (convertible to twin), a bathroom with shower, and sleeps two guests; nearby attractions include the Cheltenham Racecourse and numerous restaurants and bars.
9.6 339 reviews
Cheltenham
28/06 – 29/06
SG$169/nightfor 1 night
2 Double Bedroom Flat In The Heart Of Cheltenham
1 2
apartment , Gloucestershire
This Cheltenham flat is ideally located in the heart of the town, just a minute's walk from the main shopping area and the Everyman Theatre, and a five-minute walk from various festival venues. It has consistently received excellent ratings for its cleanliness, location, and overall experience. The flat has two bedrooms and can comfortably accommodate four guests. It features a well-equipped kitchen with a fridge and microwave oven, allowing you to prepare your own meals.
9.7 22 reviews
Cheltenham
26/06 – 28/06
SG$268/nighttotal: SG$536 (2 )
1a Vernon Court Town Centre Parking Off High St
1 4
apartment , Cheltenham
1A Vernon Court, a Cheltenham house, is situated 0.05km from Cheltenham High Street, overlooking Sandford Park and the River Chelt. This single-storey property sleeps four in two bedrooms (one king, one twin convertible to king), offering a living room, dining area, fully equipped kitchen with dishwasher, garden, parking, and excellent guest reviews.
9.6 5 reviews
Cheltenham
21/08 – 23/08
SG$408/nighttotal: SG$816 (2 )
Cheltenham Town House - Sleeps 8 - Central
1 4
house , Gloucestershire
This three-bedroom, two-bathroom flat is located on Bath Road in Cheltenham, placing it within a 5-10 minute walk of Montpelier, the Promenade, and Cheltenham town centre, with Montpellier Gardens hosting the Food & Drink and Jazz Festivals nearby, and the racecourse a short taxi ride away. This property offers accommodation for up to eight guests across three floors, featuring an open-plan kitchen and dining area, a separate living room with a sofa bed, and a secure garden with a garden room suitable for pets, all equipped with internet access.
9.8 116 reviews
Cheltenham
21/08 – 23/08
SG$518/nighttotal: SG$1036 (2 )
En Ville-maison-vue Ville-salle De Bain Privée
1 4
apartment , Gloucestershire
This modern Gloucestershire house, near Cheltenham town centre, offers a quiet, private location at the end of a cul-de-sac, convenient for exploring Cheltenham's cultural attractions and shops. The three-bedroom, two-bathroom property sleeps six, features an open-plan kitchen/diner, a separate lounge with a Smart TV, allocated parking, and complimentary Wi-Fi; additional housekeeping services are available for shorter stays.
Best family friendly Cheltenham holiday rentals
Among the 1491 accommodations in Cheltenham, here are the 4 best family friendly rentals
Cheltenham
26/06 – 28/06
SG$469/nighttotal: SG$938 (2 )
Cosy Cotswolds House
3 4
cottage , Cheltenham
This charming cottage is located just 4km from Cheltenham Town Hall and the Holst Birthplace Museum, making it a great base for exploring the town and surrounding countryside. The cottage is situated near the river, offering a peaceful and picturesque setting. This 4-bedroom property comfortably sleeps 8 guests and includes a fully equipped kitchen with a dishwasher, a garden with a barbecue, and parking. The cottage also offers internet access and heating, ensuring a comfortable and convenient stay.
9.9 68 reviews
Cheltenham
21/07 – 24/07
SG$273/nighttotal: SG$819 (3 )
Prestige-maison-salle De Bain Privée-vue Sur Rue
1 2
apartment , Gloucestershire
This Gloucestershire self-catering house is located on a quiet lane in the Suffolks and Montpellier district, a desirable area of Cheltenham. This two-bedroom retreat offers an open-plan kitchen, lounge, and dining area, a private patio, and sleeps up to four guests, with all linens, towels and toiletries provided.
10 1 review
Cheltenham
02/07 – 05/07
SG$863/nighttotal: SG$2589 (3 )
Historic & Stylish Cottage
4 3
house , Charlton Kings
Historic & Stylish Cottage is a family-friendly house in Charlton Kings, Gloucestershire, located 16km from Kingsholm Stadium and 32km from Cotswold Water Park. This 116 square metre property sleeps 13 guests in four bedrooms and two bathrooms, boasting a terrace, garden, parking, and access to a tennis court, concierge service, and nearby cycling routes; a paid airport shuttle to Bristol Airport (85km) is available.
9.4 3 reviews
Cheltenham
11/12 – 31/12
SG$395/nighttotal: SG$7900 (20 )
Cosy Peaceful Self Contained Home In Montpellier
2 3
apartment , Cheltenham
This Montpellier mews house in Cheltenham offers self-contained accommodation on a quiet lane, a short walk from Cheltenham's best bars and restaurants. The two-bedroom apartment sleeps six, featuring two en-suite shower rooms, a fully equipped kitchen with dishwasher, complimentary Wi-Fi, and allocated parking.
Best Cheltenham holiday rentals with parking
9.6 174 reviews
Cheltenham
21/08 – 23/08
SG$680/nighttotal: SG$1360 (2 )
Cambray Apartment
3 3
apartment , Cheltenham
This Cheltenham apartment, ideally located for exploring Gloucestershire, is approximately 14 kilometres from Kingsholm Stadium, 13.7 kilometres from Sudeley Castle, and 15.3 kilometres from Gloucester Cathedral. This three-bedroom, two-bathroom dwelling boasts a 9 square metre floor area, sleeps up to 11 guests, includes a jacuzzi, private hot tub, garden, parking, and offers laundry services.
9.8 5 reviews
Cheltenham
11/07 – 12/07
SG$512/nightfor 1 night
New, Luxury Apartment In Town Centre
2 2
apartment , Cheltenham
This new, luxury flat offers central Cheltenham accommodation, placing you within easy reach of shops and restaurants, with private on-site parking and complimentary high-speed WiFi. This well-appointed apartment sleeps up to seven guests across two bedrooms and features two bathrooms, a fully equipped kitchen with an oven and microwave, and a non-smoking environment.
9.7 15 reviews
Cheltenham
21/07 – 24/07
SG$239/nighttotal: SG$717 (3 )
Cosy 2-bed Apartment In Tivoli
2 2
apartment , Gloucestershire
Cosy 2-Bed Apartment in Tivoli is situated in Cheltenham, 12.4km from Kingsholm Stadium and conveniently located for exploring the town. This 74 square metre flat offers one bedroom, one bathroom, sleeps up to 11 guests, and includes free parking, Wi-Fi, a terrace, garden, and a fully equipped kitchen.
9.6 138 reviews
Cheltenham
21/07 – 24/07
SG$188/nighttotal: SG$564 (3 )
Cheltenham Studio Apartment
1 2
studio , Cheltenham
This studio apartment in Cheltenham is conveniently located within easy reach of attractions such as Weston Park, Cotswold Water Park and Coughton Court, making it an ideal base for exploring the Cotswolds. The property has consistently received excellent ratings for its cleanliness, location and overall experience. The self-catering studio apartment is perfect for couples, offering a comfortable and convenient space with a floor area of 25 square metres. Guests can enjoy a private patio, free Wi-Fi, a fully equipped kitchen with a fridge, freezer and microwave oven, as well as a garden and parking.
Frequently asked questions about holiday rentals in Cheltenham
What are the top family-friendly attractions in Cheltenham?
The Cheltenham Museum and Art Gallery is a great option for all ages. The town also has a fantastic outdoor play area at the Pittville Park, and the nearby Cotswold Farm Park is a favourite for animal lovers.
What are the best Airbnb and vacation rentals in Cheltenham?
When is the best time to book a vacation rental in Cheltenham?
Booking in advance is always a good idea, especially during peak season, which runs from late spring to early autumn. For the best deals, consider visiting during the shoulder seasons, like April or October.
What events or festivals should visitors check out in and around Cheltenham?
The Cheltenham Jazz Festival in April is a big draw, and the Cheltenham Literature Festival in October attracts writers and readers from all over. You could also check out the Cotswold Show in July for a taste of rural life.
What are the best vacation rentals with a pool in Cheltenham?
What are the best budget-friendly activities in Cheltenham?
A walk along the Promenade is always free and offers stunning views. You can also visit the free exhibits at the Cheltenham Museum and Art Gallery, or take a picnic to the Pittville Park.
What are the best rentals for families and kids in Cheltenham?
What are the best restaurants with local dishes in Cheltenham?
The Tavern is a popular spot for traditional pub grub, while The Wheatsheaf offers a more upscale dining experience with a focus on local ingredients. For a taste of the Cotswolds, try the Cotswold House Hotel.
What are the best rentals or Airbnbs with a jacuzzi in Cheltenham?
What are the best walking or cycling routes in Cheltenham?
The Cotswold Way National Trail passes through Cheltenham, offering stunning views of the countryside. For a shorter cycle, try the route along the towpath of the Gloucester and Sharpness Canal.
Are there pet-friendly attractions in Cheltenham?
Many of the parks and gardens in Cheltenham are dog-friendly, including the Pittville Park and the Montpellier Gardens. Several pubs and restaurants also welcome dogs.
What are the benefits of choosing a vacation rental in Cheltenham?
Vacation rentals often offer more space and privacy than a hotel room, and they can be a great option for families or groups. They can also be more affordable, especially for longer stays.
What are the top sports attractions and facilities in Cheltenham?
Cheltenham is famous for its horse racing, with the Cheltenham Racecourse hosting major events like the Cheltenham Festival. The town also has a number of other sporting facilities, including the Cheltenham Town Football Club and the Cheltenham Leisure Centre.
Destinations nearby
Best Cheltenham holiday rentals with a balcony
8.7 7 reviews
Cheltenham
07/08 – 09/08
SG$326/nighttotal: SG$652 (2 )
Montpellier At Regency 24
1 3
apartment , Cheltenham
This Montpellier flat at Regency 24 in Cheltenham is located 14.3 kilometres from Kingsholm Stadium and 12.7 kilometres from Sudeley Castle, offering convenient access to local attractions. This 50 square meter apartment accommodates up to seven guests and features a private balcony, complimentary private parking, free WiFi, and a fully equipped kitchen, with check-out between 08:00 and 10:00 AM.
8.7 3 reviews
Cheltenham
27/10 – 31/10
SG$154/nighttotal: SG$616 (4 )
One Bedroom House Free Parking
1 2
apartment , Gloucestershire
This one-bedroom flat in Cheltenham offers convenient access to local attractions, situated 12.87 kilometres from Sudeley Castle and 14.32 kilometres from Kingsholm Stadium. Guests can enjoy complimentary private parking, free Wi-Fi, a fully equipped kitchen, and terrace access, with a maximum capacity of three people and a check-out time of 11:00 AM.
9.7 3 reviews
Cheltenham
21/08 – 23/08
SG$955/nighttotal: SG$1910 (2 )
Comfortable & Contemporary 5-bed 3 Bathroom Home
5 4
house , Gloucestershire
This Gloucestershire holiday home is situated 14.6km from Kingsholm Stadium and 12km from Sudeley Castle, offering convenient access to Cotswold Water Park and Coughton Court. This five-bedroom, three-bathroom property boasts 167 square metres of living space, sleeps up to 14 guests, includes a fully equipped kitchen, private garden, free Wi-Fi, parking, and on-site table tennis.
9.1 20 reviews
Cheltenham
11/01 – 12/01
SG$423/nightfor 1 night
Entire 3-bed House Near Cheltenham Racecourse And Town
3 2
apartment , Gloucestershire
This Gloucestershire apartment is ideally located near Cheltenham Racecourse and town centre, approximately 16 kilometres from Kingsholm Stadium and 37 kilometres from Cotswold Water Park. This three-bedroom property boasts 82 square metres of living space, including a private garden, terrace, parking, and modern kitchen with dishwasher, comfortably accommodating up to 11 guests with excellent user ratings.
Best Cheltenham holiday rentals with air conditioning
9.0 2 reviews
Cheltenham
21/08 – 23/08
SG$654/nighttotal: SG$1308 (2 )
Stylish Converted Bakery In Central Cheltenham
1 4
apartment , Gloucestershire
This converted bakery, The Old Bakery, is centrally located in Cheltenham, Gloucestershire, offering 1 kilometer access to the town's amenities and attractions. This characterful apartment accommodates up to six guests across three bedrooms and features a fully equipped kitchen, a bath and shower, and is pet-friendly, with free on-street parking available.
Cheltenham
02/07 – 05/07
SG$374/nighttotal: SG$1122 (3 )
The Cobblestone Townhouse By Fortuna Property Portfolio
3 3
apartment , Cheltenham
This 3-bedroom, 2.5-bathroom flat in Cheltenham offers prime access to local attractions, being a 548-meter walk from Cheltenham Spa station, a 9-minute walk from the Cheltenham Art Gallery and Museum, and a 5-minute drive from Cheltenham Racecourse. With 147 square meters of floor area, this accommodation comfortably sleeps eight guests and includes air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher, and on-site parking.
10 3 reviews
Cheltenham
15/08 – 29/08
SG$345/nighttotal: SG$4830 (14 )
Contemporary 2-bed 2-bath Home With Parking
2 1
house , Gloucestershire
This contemporary 2-bedroom, 2-bathroom residence is located in Cheltenham, 11.9 kilometres from Sudeley Castle and 14.9 kilometres from Kingsholm Stadium. This 102 square meter dwelling offers accommodation for up to 7 guests, featuring a fully equipped kitchen with a dishwasher and microwave, free WiFi, and a private patio with outdoor dining, with a washing machine available for longer stays.
9.6 223 reviews
Cheltenham
27/10 – 31/10
SG$256/nighttotal: SG$1024 (4 )
Luxurious 1 Bed Detached Home With Gated Parking
1 2
house , Cheltenham
This charming house is situated in Pittville Circus Road, Cheltenham, within easy reach of Weston Park, Cotswold Water Park, and Coughton Court. The property has received excellent ratings for location, cleanliness, and user experience. The house features one bedroom and one bathroom, providing comfortable accommodation for two guests. Amenities include a terrace, a garden, parking, and a fully equipped kitchen with a fridge and microwave oven, ensuring a pleasant stay.