
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 $39 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.

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.

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.

Modern Studio Apt close to village pub & bus stop
A modern and deceptively spacious studio apartment with its own entrance less than 2 minute walk from a lively village pub, and a 2 minute walk to a main bus route into Cheltenham. All mod cons including, high speed wireless internet, 55 inch 4K TV with Freesat, PS4, underfloor heating, double bed, sofa (can be turned into another bed. Please request extra bedding if required), well appointed kitchen, with toaster, microwave and coffee machine. Bathroom with toilet, sink and electric shower.

The Garden House in Kingsholm, Gloucester
The Garden House is a lovely single room annex with independent access, en-suite bathroom and shower. Light, cosy, and simply furnished, set in the garden of a residential home near the centre of Gloucester, it's a quiet space to relax or work. Driveway parking available. A two-minute walk to the famous Kingsholm rugby stadium and food shops, ten minutes to city centre, bus and train stations, cathedral, Quays shopping outlet, restaurants and historic docks. Easy bus route to Cheltenham.

Townhouse luxury, central Grade 2 listed apartment
A newly refurbished space respecting the traditional building yet in a contemporary style. Light and airy with small outside courtyard area, and plenty of amenities to make your stay comfortable. Within walking distance of all that Cheltenham has to offer including the racecourse, fabulous restaurants and bars and beautiful parks. Also within striking distance of the stunning Cotswolds. The property is part of our family home yet is completely self contained for your enjoyment and privacy.

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.

Luxury spacious Two Bedroom Apartment, Montpellier
A luxurious spacious apartment is on the main street of Montpellier. It is quiet, being away from main roads, but in just a few steps downstairs you are on the lovely shopping street with galleries, cafes, restaurants and bars. A short stroll to the parks and shops in the centre of Cheltenham it is an ideal place to explore this lovely Cotswold town. The apartment is beautifully fitted with 2 bedrooms and 2 bathrooms. There is an allocated parking space at the back of the apartment

Studio 77 Cheltenham
You will be very welcome to stay in our brand new and beautifully renovated compact and bijou tiny home which is in an easy walk of Cheltenham Town Centre and the Racecourse. We have created a gorgeous space to the rear of our family home that is completely self contained with its own entrance. Studio 77 comprises of a king size bed, kitchenette area, small seating arrangement and a good sized shower room. There is a small private patio area for guests to enjoy on a sunny evening.

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.

Central Cosy Terraced Victorian 2 Bedroom Cottage
Enjoy easy access to everything from this perfectly located cottage. Set in the heart of Cheltenham, the property is ideally located to access all the Town has to offer. Within walking distance of the Town Centre, The Suffolks, Montpellier and Bath Road this is perfectly situated for shopping, dining and exploring. A perfect base for business guests or those wishing to explore Cheltenham and The Cotswolds.
Popular amenities for Cheltenham family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Cabin with Hot-Tub & Cold Plunge!

Central penthouse with private hot tub and views

Lodge farm Woodland dome. Hot tub. luxury escape

Town Centre Penthouse with Hot Tub 22

Rural, character 2 bed cottage and hot tub

Traditional 6br farmhouse

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

Becketts Farm Shepherd’s hut
Family- and pet-friendly home rentals

Cotswold lodge with amazing views and famous walks

Prestbury Village Annexe.

Fantastic isolation Cotswolds hideaway Cleeve Hill

The Stables - Luxury Central Cheltenham Bolthole

Cottage luxe in The Cotwolds

Modern 4 Bedroom 4 Bathroom Home in Cheltenham

Chapel End

Beautiful Barn in the Cotswolds
Family-friendly home rentals with a pool

Charming Stone Cotswold Cottage with Pool Access

Cotswolds, Private Pool. Celebrations & Gatherings

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

Cotswolds Cottage, Heated Pool, Tithe Barn Views

Lower Mill Estate - 43 Clearwater + Pools + Lakes
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $260 SGD | $251 SGD | $376 SGD | $248 SGD | $261 SGD | $264 SGD | $279 SGD | $281 SGD | $257 SGD | $273 SGD | $268 SGD | $294 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
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- Rentals with a hot tub Cheltenham
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- Rentals with a firepit Cheltenham
- Family-friendly rentals Gloucestershire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Silverstone Circuit
- Cotswolds AONB
- University of Oxford
- National Exhibition Centre
- Blenheim Palace
- Longleat Safari Park
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Highclere Castle
- Cheltenham Racecourse
- West Midland Safari Park
- University of Warwick
- Utilita Arena Birmingham
- Cadbury World
- Ludlow Castle
- Cotswold Wildlife Park
- Bath Abbey
- Coventry Building Society Arena
- Sudeley Castle
- Puzzlewood
- University of Birmingham
- Waddesdon Manor
- No. 1 Royal Crescent
- Bicester Village





