Holiday Rentals in Cheltenham

1491 available vacation rental offers

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

Best Holiday rentals and Airbnb offers in Cheltenham

Best family friendly Cheltenham holiday rentals

Among the 1491 accommodations in Cheltenham, here are the 4 best family friendly rentals

Peaceful 3-bed Home In Tivoli - Cheltenham
8.0 1 review
Cheltenham
01/07 – 04/07
SG$347/nighttotal: SG$1041 (3 )

Peaceful 3-bed Home In Tivoli

3 2
apartment , Gloucestershire
This Cheltenham holiday home, ideally located for exploring Gloucestershire, is approximately 8km from Gloucester Docks and Gloucester Quays, offering easy access to attractions such as Walks With Hawks and Barnwood Arboretum & Park.
The self-catering apartment sleeps six guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen, private balcony, and on-site laundry facilities; nearby activities include exploring the city's attractions or enjoying the surrounding nature.
Charming Two Bedroom Apartment In Fairview - Cheltenham
8.0 1 review
Cheltenham
04/09 – 04/10
SG$229/nighttotal: SG$6870 (30 )

Charming Two Bedroom Apartment In Fairview

2 3
apartment , Gloucestershire
This Cheltenham apartment, near Cheltenham Racecourse, offers convenient access to Gloucester Docks and Gloucester Quays, and is a short distance from Elmore Court.
The two-bedroom flat sleeps four, includes a fully equipped kitchen with dishwasher and washing machine, a private balcony, and on-site parking.
The Mitre, Cheltenham, Stylish, Sleeps 8, Parking, Central - Cheltenham
9.7 8 reviews
Cheltenham
28/06 – 29/06
SG$872/nightfor 1 night

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.
69 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Cheltenham
Cheltenham
06/08 – 08/08
SG$282/nighttotal: SG$564 (2 )

69 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment
This Cheltenham apartment is centrally located, a 0.8km walk from Regent Arcade shopping centre and a short stroll from the Everyman and Playhouse theatres.
The 68 square metre flat offers three bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen, parking, and a balcony; high-speed broadband is provided.

Best Cheltenham holiday rentals with parking

Central Cheltenham, Regency 1st Floor Apartment With Parking, Cavalier Suite - Sleeps 6 - Cheltenham
8.8 43 reviews
Cheltenham
06/08 – 08/08
SG$421/nighttotal: SG$842 (2 )

Central Cheltenham, Regency 1st Floor Apartment With Parking, Cavalier Suite - Sleeps 6

2 4
apartment , Cheltenham
The Cavalier Suite is a Regency apartment in central Cheltenham, just 7.7 kilometres from Sudeley Castle and within easy walking distance of the town's shops, restaurants, and attractions. Guests consistently rate it highly for its cleanliness, location, and overall experience.
This two-bedroom apartment spans 55 square metres and comfortably accommodates up to six guests. The Cavalier Suite offers a fully equipped kitchen, free parking, garden views, free Wi-Fi, and a comfortable living space with a flat-screen TV.
Stylish 2-bed Home Close To Cheltenham Town Centre - Cheltenham
Cheltenham
02/07 – 05/07
SG$304/nighttotal: SG$912 (3 )

Stylish 2-bed Home Close To Cheltenham Town Centre

1 3
house , Cheltenham
This 2-bedroom dwelling is situated close to Cheltenham Town Centre.
This 93 square meter house offers a family-friendly stay with a garden, parking, and a kitchen equipped with a fridge and microwave, plus free Wi-Fi.
Thornton House Luxury Accommodation In The Town Centre With Private Parking - Cheltenham
9.8 100 reviews
Cheltenham
20/08 – 21/08
SG$315/nightfor 1 night

Thornton House Luxury Accommodation In The Town Centre With Private Parking

1 4
apartment , Cheltenham
This recently renovated Cheltenham town centre flat offers free private parking, a significant advantage given limited availability, and is conveniently located 12.7km from Sudeley Castle and 13.7km from Kingsholm Stadium.
The 70 square metre self-catering apartment features one bedroom, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with dishwasher, a private terrace with city views, and free Wi-Fi.
Eclectic 1bd In The Heart Of Cheltenham! - Cheltenham
9.1 12 reviews
Cheltenham
15/08 – 29/08
SG$227/nighttotal: SG$3178 (14 )

Eclectic 1bd In The Heart Of Cheltenham!

1 1
apartment , Cheltenham
This Cheltenham apartment enjoys a central location, conveniently situated 13km from Kingsholm Stadium and approximately 14km from both Sudeley Castle and Gloucester Cathedral.
The 18 square metre self-catering flat features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen with fridge, microwave, and washing machine, plus free Wi-Fi.

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?

    Portland Apartments, Strozzi Palace Suites By Mansley and Tewkesbury Town House are the most popular Airbnb and vacation rentals in Cheltenham among travelers.

  • 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 are the most popular Airbnbs in Cheltenham?

    Among the Airbnbs in Cheltenham, Tewkesbury Town House, Mike's Flat 5 and Cotswold77 - Heart Of The Cotswolds are the most popular ones.

  • 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

Pittville Lawn - By Luxury Apartments - Cheltenham
10 1 review
Cheltenham
11/09 – 18/09
SG$279/nighttotal: SG$1953 (7 )

Pittville Lawn - By Luxury Apartments

1 2
apartment , Gloucestershire
Pittville Lawn apartment is situated in Gloucestershire, close to Cheltenham, 12km from Sudeley Castle and within a 14km radius of Kingsholm Stadium.
This one-bedroom flat offers 70 square metres of space, sleeping up to three guests, and boasts a private terrace with garden views, a fully equipped kitchen including a dishwasher, free Wi-Fi and private parking.
Homely Regency Style House In The Heart Of Cheltenham - Cheltenham
9.9 15 reviews
Cheltenham
06/07 – 08/07
SG$419/nighttotal: SG$838 (2 )

Homely Regency Style House In The Heart Of Cheltenham

3 2
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.
Luxury Woodland Stay - Private Walks - Just Refurbished - Cheltenham
10 4 reviews
Cheltenham
21/08 – 23/08
SG$490/nighttotal: SG$980 (2 )

Luxury Woodland Stay - Private Walks - Just Refurbished

2 4
apartment , Cheltenham
This recently refurbished two-bedroom flat in Cheltenham offers a tranquil woodland setting, located 14.16 kilometres from Lydiard Park, 14.16 kilometres from Gloucester Cathedral, and 13.99 kilometres from Kingsholm Stadium.
This 38 square metre accommodation sleeps up to 13 guests and features two living rooms, a fully equipped kitchen, complimentary WiFi, free private parking, and a garden with a terrace.
Historic & Stylish Cottage - Cheltenham
10 1 review
Cheltenham
11/01 – 12/01
SG$863/nightfor 1 night

Historic & Stylish Cottage

4 2
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.

Best Cheltenham holiday rentals with air conditioning

Racing Accommodation On Course - Cheltenham
Cheltenham
01/08 – 31/07
SG$2245/nighttotal: SG$817180 (364 )

Racing Accommodation On Course

1 1
apartment , Southam
This family-friendly guesthouse is situated within Southam's racecourse, offering convenient access to the course's facilities and attractions.
The five-bedroom property boasts three bathrooms, sleeps up to twelve guests, and includes a kitchen, parking, and air conditioning, alongside a spacious yard with ducks.
Prestige-maison-salle De Bain Privée-vue Ville-hom - Cheltenham
10 39 reviews
Cheltenham
21/08 – 23/08
SG$2238/nighttotal: SG$4476 (2 )

Prestige-maison-salle De Bain Privée-vue Ville-hom

1 3
apartment , Gloucestershire
This exceptional Cheltenham property, close to the Cotswolds Area of Outstanding Natural Beauty, offers easy access to picturesque villages and landscapes.
Sleeping up to 12 guests in six bedrooms and three bathrooms, this six-bedroom house boasts a spacious open-plan kitchen, lounge, and dining area, a landscaped garden with private gym and sauna, and private parking for at least four cars.
Comfy Modern Home, Entire Flat, King Size Bed - Cheltenham
9.7 18 reviews
Cheltenham
01/08 – 02/08
SG$193/nightfor 1 night

Comfy Modern Home, Entire Flat, King Size Bed

1 2
apartment , Gloucestershire
This one-bedroom flat is ideally situated in a peaceful area of Gloucestershire, close to local attractions and amenities. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The flat comfortably accommodates up to four guests with a king-size bed in the bedroom and a sofa bed in the open plan kitchen and living area. Guests can enjoy modern appliances, free parking, and a peaceful retreat after a day of exploring Gloucestershire.
Winchcombe Cottage With Breathtaking Views - Cheltenham
Cheltenham
07/08 – 09/08
SG$597/nighttotal: SG$1194 (2 )

Winchcombe Cottage With Breathtaking Views

1 3
apartment , Winchcombe
This Cheltenham flat offers countryside views and is situated near the Cotswold Way, Sudeley Castle, and Winchcombe's cultural attractions, placing you 1.5 kilometers from Winchcombe's centre.
This one-bedroom flat accommodates up to five guests and features air conditioning, Wi-Fi, a private garden, and parking, with direct access to walking routes ideal for exploring the Cotswolds.
©2026 cozycozy.com