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.

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Top guest favourite
An open-plan living area features a wooden dining table with six chairs and a cozy seating arrangement. A large sofa faces a coffee table, while plants add a touch of greenery. Natural light fills the space through large windows, enhancing the inviting atmosphere.
Home in Gloucestershire
5 out of 5 average rating, 297 reviews

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.

Superhost
A modern kitchen space features sleek white cabinets and an integrated oven. A wooden countertop provides an inviting area for meal preparation, while stainless steel appliances complement the clean design. Natural light enters through a nearby window, enhancing the bright and functional atmosphere.
Apartment in Gloucestershire
4.87 out of 5 average rating, 383 reviews

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.

Top guest favourite
An open-plan living space features a striking loft with a glass design above a cozy seating area. A patterned sofa and a coffee table sit on a red rug. A staircase leads to the loft, while the kitchen area is visible in the background.
Apartment in Gloucestershire
4.95 out of 5 average rating, 161 reviews

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.

Guest favourite
A self-contained studio flat features a spacious bed with colorful bedding and freshly folded towels placed on top. A cozy sofa complements the room, with a large window allowing natural light to fill the space. A small alcove with a mirror is positioned nearby.
Flat in Gloucestershire
4.84 out of 5 average rating, 148 reviews

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).

Guest favourite
A modern living area features a cozy grey sofa adorned with soft pink cushions, complemented by a comfy armchair with a decorative throw. A round mirror is positioned on the wall, while framed artwork adds a touch of sophistication. Warm lighting extends across the space.
Flat in Gloucestershire
4.92 out of 5 average rating, 210 reviews

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.

Top guest favourite
A cozy sleeping area features a wooden bed with soft bedding, accented by light-colored walls. A bathroom with a glass shower is visible through an open door, showcasing modern fixtures and a clean aesthetic.
Apartment in Gloucestershire
4.98 out of 5 average rating, 135 reviews

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.

Top guest favourite
A domed structure, partially covered in greenery, is visible surrounded by trees in a private woodland setting. A hot tub sits prominently in the foreground, with a wooden deck and outdoor seating area adjacent to the dome, inviting relaxation in nature.
Dome in Milbury Heath
4.99 out of 5 average rating, 189 reviews

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!

Superhost
A cozy living area features a deep red sofa adorned with patterned cushions, positioned against light grey walls. A reflective mirror hangs above a traditional fireplace. A soft area rug covers the floor, complemented by a warm table lamp casting a gentle glow.
Apartment in Gloucestershire
4.88 out of 5 average rating, 134 reviews

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.

Top guest favourite
A large, pale yellow building is featured with a grand entrance and multiple windows. A flowering tree with pink blossoms is visible in the foreground, surrounded by a gravel pathway and well-maintained greenery, enhancing the inviting exterior of the property.
Apartment in Gloucestershire
4.95 out of 5 average rating, 149 reviews

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

Guest favourite
The exterior features a newly refurbished annexe with a clean, modern design. A stone pathway leads to a private entrance, surrounded by gravel and paving. A small area of artificial grass and a garden shed are visible, providing a welcoming outdoor space.
Guest house in Gloucestershire
4.91 out of 5 average rating, 395 reviews

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.

Guest favourite
A comfortable bedroom is highlighted by a spacious bed with a light-grey headboard. Decorative pillows add texture. Two bedside lamps provide soft illumination. Artwork featuring a tree and Cheltenham-themed prints adorn the walls, contributing to a cozy and inviting ambiance.
Apartment in Gloucestershire
4.91 out of 5 average rating, 240 reviews

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.

Top guest favourite
The lounge area features two comfortable sofas, one adorned with bright orange cushions. A small coffee table holds a collection of magazines. A decorative fireplace serves as a focal point, and a muted art piece hangs above it, contributing to a cozy ambiance.
Serviced apartment in Cheltenham
4.97 out of 5 average rating, 100 reviews

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

When is the best time to visit Cheltenham?

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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
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