
Family-friendly holiday rentals in Cheltenham
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Cheltenham

Total holiday rentals
Explore 820 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 26,510 verified reviews to help you choose

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wifi availability
810 of Cheltenham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cheltenham rentals

4.9 Average rating
Cheltenham stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Cheltenham’s top spots include Cheltenham Racecourse, Pittville Park and Everyman Theatre
Top-rated family-friendly rentals in Cheltenham
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Charming Coach House, fab location, highly rated!
A beautifully converted 2-bedroom Coach House in the desirable Leckhampton district of Cheltenham offers stylish living with the added benefit of free on-street parking. Ideally situated near the fashionable Bath Road and just a short stroll from the lively Montpellier & Suffolk areas, guests can enjoy a vibrant atmosphere filled with bars, cafés, restaurants, and boutique shops. The interior boasts high-specification design, making it a perfect blend of comfort and elegance in a prime location.

Modern studio in the heart of Cheltenham
Enjoy your stay in this centrally located studio apartment on the top ( second ) floor. Ideally located for all the wonderful bars cafes and restaurants that Cheltenham has to offer, this easy living, modern studio apartment is on the doorstep to all the activity. You will see instructions for entry 48 hours before arrival. GL52 2SQ There is a secure side door for bike storage on ground floor. Cheltenham Racecourse is a 5 minute drive ( traffic dependent ) or a 30 minute walk from apartment.

Pittville Loft - 5* Free parking no cleaning fee
The hidden gem of hidden gems. Our beautiful apartment is nestled in a quiet private mews lane - close to all you need and want in central Cheltenham. Free Parking inc Pittville Loft is perfectly situated for couples, young families, small groups of friends and single people traveling for business or pleasure. Within easy walking distance to the festival sites and the racecourse. Quirky and unique, Pittville Loft combines all modern conveniences with stylish vintage style and industrial chic.

New Town Centre Studio Flat
Whatever you’re in Cheltenham for, this newly renovated self-contained studio flat is the perfect location for your stay. 5 minutes walk from the high street and from the fantastic bars and restaurants of Montpellier. Round the corner from the hospital and with the beautiful Sandford Park Gardens and Lido on the doorstep. The studio is the ideal bolthole with permit parking available, key pad entry, kitchen area, newly fitted bathroom, bedroom area and sofa (sofa bed for an additional fee).

Best located Flat in Cheltenham + Free Parking
Luxury, modern, 5* apartment in the heart of Montpellier, Cheltenham. Centrally located, just a minutes walk from Cheltenham’s prestigious shopping on The Promenade. Montpellier bustles with bars & restaurants including The Ivy and 131. The apartment is set back off Montpellier Street in The Courtyard so has more privacy. A huge benefit is the free of charge, private parking space. If you’re here for one of Cheltenham’s festivals Imperial Gardens and Montpellier Gardens are opposite the flat.

Charming boutique suite in Cheltenham town
Charming boutique style basement suite in Cheltenham Regency townhouse. Accommodation offers private lounge area, en-suite and bed annex. Adjoining tea and coffee facility with fridge and seating area included. Minutes from town centre with its many restaurants, theatres and shopping areas. All main festivals within walking distance, 20 mins to Racecourse, 10 mins to most others, Jazz, Science, Music, Cricket and Literature. Great access to the Cotswolds and the famous Cotswold Way.

Lodge farm Woodland dome. Hot tub. luxury escape
A luxurious dome nestled in private woodland and flower garden. An ideal romantic/ family stay near the Cotswolds. Enjoy the wildlife view from your king size bed, woodburning stove, additional heating and air conditioning. Relax on the private decking area, outdoor dining with a barbeque and firepit for toasting marshmallows amongst the trees. The mattresses can be brought down from the loft area for younger children. Rest, relax and reward yourself with the glamping stay with us!

Stylish, town centre apartment with free parking
Fantastic location for a city centre stay. Beautiful, regency apartment, with original Georgian features, spacious rooms and luxury interior. Town centre location, 5 minute walk to John Lewis. Also walking distance to Cheltenham Racecourse. The apartment is fully equipped with Wi-Fi, fully heated and powerful water pressure! There are two bedrooms, a fully equipped kitchen, one bathroom, one luxury en-suite, This is a perfect base from which to explore Cheltenham and the Cotswolds.

Cosy Cheltenham Hideaway
We love to welcome guests to our home and offer a large self-contained Lower Ground Floor 1 bed apartment, with its own front door, allowing guests to come and go as they please. The property has a kitchen dinner, with microwave for convenience. A large sitting room with 42” TV. There is also a log burner which guests are welcome to use. The bedroom has a new Hypnos mattress. Finally there is bathroom with walkin shower. There is also secure off-street parking on the drive

Beautiful Self-Contained Annexe in Cheltenham
A lovely, newly refurbished annexe, perfect for 1 or 2 guests within good distance to the town center. A cosy, fully functioning, self-contained home from home featuring a double bed, kitchenette, en suite bathroom, 32" TV, heated floor and radiator with a private entrance. Located a 30 minute walk from the town centre and the Brewery Quarter, which is full of restaurants and bars, 2 cinemas, Mr Mulligans Adventure Golf and Hollywood Bowl.

Stylish apartment in the heart of Cheltenham
A chic stylish one bedroom apartment in a Victorian townhouse in the centre of Cheltenham with FREE PARKING. Perfectly located to experience all Cheltenham has to offer. A short walking distance to festival locations and the most popular bars and restaurants in Montpellier, The Suffolks, Bath Road and the Promenade. The racecourse is a 25 minute walk or 10 minutes by road. An ideal base for those travelling for business or pleasure.

Luxury Refurbished 2 Bedroom Regency Apartment
Superbly Appointed Regency Apartment Situated Along A Tree Lined Road Close To Cheltenham Centre Where You Will Find A Plethora Of Amazing Shops & Restaurants. With Its Own Private Entrance This Luxury Apartment Has Been Refurbished To A High Standard Throughout & Offers Spacious & Comfortable Living. It Is Suitable For Up To 4 Guests, Couples, Families Or Corporate Stays.
Popular amenities for Cheltenham family-friendly rentals
Family-friendly home rentals with a hot tub

Riverside Cottage

Luxury Cabin with Hot-Tub & Cold Plunge!

Town Centre Penthouse with Hot Tub 22

Magical cottage set within a woodland glade

Foston's Ash Shepherd's Hut (Lawlessdown:blue hut)

Becketts Farm Shepherd’s hut

Luxury boutique holiday Cottage, 2 bed, 2 bathroom

Private, luxurious and cosy shepherd hut
Family- and pet-friendly home rentals

May Hill Woodlands Safari Tent

Cotswold lodge with amazing views and famous walks

The Organic Cotswolds Cowshed

Cottage luxe in The Cotwolds

Beautiful Barn in the Cotswolds

Large Period 2-Bed Apartment Close to Town

Beautiful & Vast Central Apartment Free Parking

Townhouse luxury, central Grade 2 listed apartment
Family-friendly home rentals with a pool

Dovecote Cottage

The Potting Shed, 5* ❤︎ Luxury escape Cirencester

Boundary Court Barn, Selsley common, Stroud

Deluxe Coach House at Bretforton Manor with pool

Cosy, rural apartment with breakfast hamper

Luxury Cosy Cottage with Garden

43 Clearwater - Lower Mill Estate + Pools + Spa

Self contained studio apartment
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $228 SGD | $227 SGD | $367 SGD | $244 SGD | $257 SGD | $260 SGD | $275 SGD | $276 SGD | $253 SGD | $269 SGD | $264 SGD | $289 SGD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 17°C | 15°C | 11°C | 7°C | 5°C |
Destinations to explore
- House rentals Cheltenham
- Smoking-friendly rentals Cheltenham
- Fitness-friendly rentals Cheltenham
- Bed and breakfasts Cheltenham
- Private suite rentals Cheltenham
- Rentals with outdoor seating Cheltenham
- Rentals with breakfast Cheltenham
- Flat rentals Cheltenham
- Rentals with a washing machine and dryer Cheltenham
- Serviced apartment rentals Cheltenham
- Rentals with a firepit Cheltenham
- Rentals with an EV charger Cheltenham
- Guest house rentals Cheltenham
- Cottage rentals Cheltenham
- Rentals with a patio Cheltenham
- Townhouse rentals Cheltenham
- Rentals with a fireplace Cheltenham
- Rentals with lake access Cheltenham
- Apartment rentals Cheltenham
- Villa rentals Cheltenham
- Cabin rentals Cheltenham
- Pet-friendly rentals Cheltenham
- Rentals with a hot tub Cheltenham
- Family-friendly rentals Gloucestershire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Utilita Arena Birmingham
- Cheltenham Racecourse
- Silverstone Circuit
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- West Midland Safari Park
- Cadbury World
- Bath Abbey
- Sudeley Castle
- Ludlow Castle
- Waddesdon Manor
- National Exhibition Centre
- No. 1 Royal Crescent
- Puzzlewood
- Coventry Cathedral
- University of Warwick
- Eastnor Castle
- Longleat Safari Park
- Shakespeare's Birthplace
- Dyrham Park
- Hereford Cathedral




