
Family-friendly holiday rentals in Cheltenham
Find and book unique family-friendly homes on Airbnb
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.

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).

Stunning Regency Retreat; pool, garden and parking
A peaceful and spacious 1200 sqft two bed apartment taking up the entire top floor of our eight bedroomed Regency Villa, on one of central Cheltenham's finest residential roads. Perfectly situated and providing the best of both worlds : a short stroll, 0.8 miles, to the shops, bars and restaurants of Cheltenham, combined with a relaxing private garden and heated swimming pool. The Cotswold Way, for walking trails, is close by. A great base for girls weekends, families, and couples.

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.

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.

Montrose Lodge Regency Apartment, free parking(x2)
A beautifully refurbished Regency-style apartment in a superb central location. With permit street parking included for 2 vehicles within zone 1, extended parking times are available on request. The accommodation has been renovated to a high standard, featuring high ceilings, elegant period detailing, and a spacious, light-filled interior. Just a short walk to Montpellier and the Imperial Gardens, the perfect base to explore wonderful Cheltenham and all it has to offer.

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.

Two Double Bedrooms Guest Annexe with EV Charging
A 2 Bedroom guest annexe within 100 yards of Cheltenham Race Course and within a 10 minute walk to the Town Centre. This property is tucked in the grounds of the main house and offers secure gated parking. The accommodation comprises open plan living space with fantastic views of Cleeve Hill and two double bedrooms. Use of laundry facilities and home gym if required (Subject to Availability). EV Charging available (separate charge).

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.

Entire quiet flat town centre - Free parking
First floor refurbished flat accessible with lift, ideally situated a few steps away from the High Street and all commodities pubs restaurants shops. Very quiet flat days and nights (facing backyard). Modern and stylish kitchen with dining area. Sleeping arrangements: -Double bed with built-in wardrobes. -Living room with best quality convertible sofa. Free Wifi, large TV in the living room and bedroom with Netflix & Prime.
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

Magical cottage set within a woodland glade

Romantic Idyllic Nuthatch Cottage with Hot Tub

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

Cotswold lodge with amazing views and famous walks

Luxury Thatched Cotswold Cottage, amazing location

Luxury Barn conversion Cotswold’s with Sauna/Spa

The Stables - Luxury Central Cheltenham Bolthole

Cottage luxe in The Cotwolds

Town Centre Apartment with Hot Tub

Chapel End

Cotswold Farm Hideaway; Whitehall& Willow Cottages
Family-friendly home rentals with a pool

40% off in June. Private Heated Pool.

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

Stylish Cotswolds Retreat w/ Heated Pool, Sleeps 8

Cotswolds Cottage, Heated Pool, Tithe Barn Views

Hayloft Cottage - hot tub & indoor swimming pool
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $257 SGD | $248 SGD | $372 SGD | $245 SGD | $258 SGD | $260 SGD | $276 SGD | $277 SGD | $254 SGD | $269 SGD | $264 SGD | $290 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 |
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
Destinations to explore
- House rentals Cheltenham
- Smoking-friendly rentals Cheltenham
- Private suite rentals Cheltenham
- Rentals with an EV charger Cheltenham
- Rentals with a washing machine and dryer Cheltenham
- Cottage rentals Cheltenham
- Flat rentals Cheltenham
- Guest house rentals Cheltenham
- Bed and breakfasts Cheltenham
- Serviced apartment rentals Cheltenham
- Rentals with a firepit Cheltenham
- Townhouse rentals Cheltenham
- Pet-friendly rentals Cheltenham
- Rentals with breakfast Cheltenham
- Rentals with lake access Cheltenham
- Fitness-friendly rentals Cheltenham
- Cabin rentals Cheltenham
- Apartment rentals Cheltenham
- Rentals with a patio Cheltenham
- Rentals with a hot tub Cheltenham
- Rentals with outdoor seating Cheltenham
- Villa rentals Cheltenham
- Rentals with a fireplace Cheltenham
- Family-friendly rentals Gloucestershire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Utilita Arena Birmingham
- Lower Mill Estate
- Silverstone Circuit
- Highclere Castle
- Cheltenham Racecourse
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- West Midland Safari Park
- Cadbury World
- Bath Abbey
- Ludlow Castle
- University of Warwick
- Sudeley Castle
- Waddesdon Manor
- No. 1 Royal Crescent
- Puzzlewood
- National Exhibition Centre
- Coventry Cathedral
- Mendip Hills
- Coventry Building Society Arena
- Eastnor Castle
- The International Convention Centre





