
Family-friendly holiday rentals in Cheltenham
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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.

Elegant regency garden flat with parking
This property is located conveniently in the centre of Cheltenham Spa town, with one parking space. Available from 4pm check in. To 12 noon check out only. The location is very convenient for sight seeing and business trips alike. Two minutes walk to the town centre, restaurants and bars, but tucked away from noise. This property also benefits from spacious rooms and a secluded, private patio garden leading off of the master bedroom. The TV is connected by Wi-Fi to various apps and stations

Annexe in the foothills
Kick back and relax in this calm, stylish space. A newly created annex nestled in the foothills of Leckhampton Hill. 2 minute walk to an Area of Outstanding Natural Beauty and 15 minute walk from the Cotswold Way. This beautiful, bijou annexe is self contained, with private entrance and off road parking, in a quiet, residential cul de sac. Finished to a very high standard throughout with double bed, sofa, smart TV, shower room, and kitchen with workspace. 30 minute walk into Regency Cheltenham.

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).

Little Nook Cottage - Dog Friendly & Large Garden
Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

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.

Bright spacious private annex in a great location
Bright and spacious private recently built self-contained annex within a friendly family home. Ideal quiet location, close to town, local amenities, bars and restaurants. Close to Bath Road, bus stops, hospital and train station. Separate entrance with key safe entry. Small new kitchen area with hob, fridge, microwave and kettle. Lounge area has large comfy sofa and TV. Views into a large garden with own seating on the decking. Comfy bed, own bathroom with shower. Off road free parking.

The Best address in Montpellier, Cheltenham
This wonderfully spacious apartment is situated in the heart of fashionable Montpellier where you will find an incredible array of Independent shops and prestigious eateries such as The Ivy ,Giggling Squid , The Daffodil and the renowned Michelin starred Le Champignons Savage,a new find is Kibousushi located about 200 metres from the apartment ,a new find for us and an amazing Japanese restaurant ,but you have to book in advance . The home of horse racing is just a 20 minute walk .

7 Diamond Jubilee, Cheltenham
Diamond Jubilee is a unique fully electric property located in a quiet little mews street but a short walk to the bars, shops, and restaurants of the vibrant area of The Suffolks and Montpellier. Cheltenham has a thriving cultural scene and hosts numerous festivals throughout the year such as the jazz, food and drink, literature, and science. Undoubtedly, the highlight of the year is the annual racing festival, The Gold Cup at Cheltenham Racecourse. Newly renovated bathroom.

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 Regency basement flat with free parking
* Stylish, cosy and clean basement flat in a listed Regency townhouse * 5 minute walk to the heart of Cheltenham - The Prom * Great night’s sleep in a comfortable double bed * Living room with small dining table * Well-equipped kitchen * Separate bathroom with walk-in shower * Free wi-fi * Free parking right outside the flat * Sofa bed for 3rd guest if required (additional fee) * Ideal base for business/leisure, solo travellers or couples

The Garden retreat
The Garden room has its own front and back door, and access to a lovely south facing garden. It has a kitchenette and en suite. It has a very comfortable king-size bed. We are 10-15 minutes walk from the town centre and have views onto Cleeve Hill the highest point of the Cotwolds. There are good local pubs, a national award winning fish and chip shop and a supermarket all nearby. Perfectly situated for all Cheltenham festivals.
Popular amenities for Cheltenham family-friendly rentals
Family-friendly home rentals with a hot tub

Garden Annexe, Gloucester

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Chapel End
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Dovecote Cottage

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The Ndoro Carriage with use of A Natural Pool.

Deluxe Coach House at Bretforton Manor with pool

Cosy, rural apartment with breakfast hamper

Luxury Cosy Cottage with Garden

Cosy cottage with wonderful views and pool.
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $310 NZD | $309 NZD | $499 NZD | $333 NZD | $350 NZD | $354 NZD | $374 NZD | $376 NZD | $345 NZD | $338 NZD | $364 NZD | $348 NZD |
| 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 750 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 25,040 verified reviews to help you choose

Pet-friendly accommodation
Find 190 rentals that welcome pets

Rentals with dedicated workspaces
290 properties have a dedicated workspace

Wi-Fi availability
740 of Cheltenham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Silverstone Circuit
- Lower Mill Estate
- Cheltenham Racecourse
- West Midland Safari Park
- Cadbury World
- Sudeley Castle
- Ludlow Castle
- Waddesdon Manor
- Bath Abbey
- No. 1 Royal Crescent
- Coventry Cathedral
- Puzzlewood
- Shakespeare's Birthplace
- Bowood House and Gardens
- Hereford Cathedral
- Royal Shakespeare Theatre
- Dyrham Park
- Lacock Abbey
- Manor House Golf Club
- Painswick Golf Club




