Family-friendly vacation 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.

%{current} / %{total}1 / 1
Top guest favorite
The exterior of a charming brick building is displayed, featuring a symmetrical design with large windows framed in white. A subtle front door with a circular window is central, flanked by neatly arranged planters and greenery, creating a welcoming presence.
Apartment in Henleaze
4.98 out of 5 average rating, 204 reviews

Beautiful basement flat. Leckhampton, Cheltenham

Beautiful self contained basement flat with own entrance. Open plan living area with pull down ‘Murphy bed’ (please ask when booking if you would like to use this bed as it requires host assembly). Full kitchen-dishwasher,oven,microwave & washing machine. Bedroom with wardrobe, dressing table and king size bed- can be separated into 2 singles on request at time of booking. Wet room with shower. Shampoo,conditioner,shower gel and towels provided. Tea,coffee,milk and breakfast items provided.

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.
Condo in Henleaze
4.88 out of 5 average rating, 352 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 favorite
A vibrant seating area features a colorful chaise lounge adorned with various fabrics. Natural light enters through two windows, illuminating a small dining table and two chairs. A plant adds a touch of greenery in the corner, enhancing the inviting atmosphere.
Apartment in Henleaze
4.92 out of 5 average rating, 173 reviews

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

Top guest favorite
The entrance to the Garden House is framed by a sturdy tree and vibrant potted plants, showcasing colorful flowers. A wooden table and shelf stand beside the door, enhancing the welcoming appearance of this independent annex.
Tiny home in Gloucestershire
4.93 out of 5 average rating, 727 reviews

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.

Guest favorite
A private garden studio is shown alongside a manicured garden, featuring a stone pathway lined with soft grass. Contemporary wooden fencing provides privacy, while a small tree adds a natural touch. Seating areas with chairs are visible, inviting outdoor relaxation.
Guest suite in Henleaze
4.89 out of 5 average rating, 122 reviews

Detached Garden Room in Cheltenham

Beautiful private garden studio, perfect for a couple for the races or weekend in Cheltenham or the Cotswolds. Continental breakfast included on the first day. Enjoy visiting one of the famous Cheltenham festivals. Private entrance with parking, patio, table & chairs. Opposite a great pub. 3.2 miles/9mins from Cheltenham racecourse. The hosts are very welcoming & are on hand to help with restaurant or bar recommendations. There’s so much to see & do in Cheltenham & the surroundings area.

Top guest favorite
A spacious sitting area features a light-colored sofa and a wooden coffee table on a patterned rug. Glass doors open to a private patio with outdoor seating, surrounded by greenery. An original marble fireplace adds character to the room, and a television is positioned beside a wooden media unit.
Apartment in Henleaze
5 out of 5 average rating, 123 reviews

Rosebank - Spacious apartment in Montpellier.

Welcome to Rosebank, a self-contained basement apartment with a spacious, homely and creative vibe. The bedroom has a king size sleigh bed. There is a private entrance at the front and access at the back to your own south facing courtyard. Where possible a free guest parking permit can be arranged. Montpellier is a vibrant and chic area with excellent restaurants, bars & boutique shops. Easy access to the outstanding cotswold countryside makes it the perfect location for holidays or work.

Top guest favorite
A bright studio space is furnished with a wooden bed draped in white linens and a teal throw. A cozy sofa is positioned beside a TV, with a small kitchenette featuring modern amenities. Natural light illuminates the area through large windows that overlook a garden.
Guest suite in Henleaze
4.99 out of 5 average rating, 152 reviews

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.

Top guest favorite
The kitchen area features a light marble countertop with a sink, complemented by modern pendant lighting. In the background, a cozy living room is visible, furnished with a dark sofa and colorful cushions, highlighted by natural light from large windows.
Apartment in Henleaze
4.93 out of 5 average rating, 321 reviews

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 .

Top guest favorite
An open-plan living and dining area is showcased, featuring a large dining table with red chairs. A patterned area rug lies on the floor, while a comfortable seating arrangement is visible in the background. Soft lighting is provided by pendant fixtures above the table.
Home in Henleaze
4.95 out of 5 average rating, 133 reviews

Charming house in the centre of town.

A centrally located charming house. Just a short walk from the trendy Montpellier area and High Street it’s perfect for a city break. The house has a spacious open plan living/dining area with separate kitchen, two spacious bedrooms, bathroom and courtyard garden. There is a comfy fold down king size Murphy bed in the living room. Included in your booking is a parking permit for one vehicle. Additional parking permit available for a small fee.

Top guest favorite
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.
Guesthouse in Henleaze
4.91 out of 5 average rating, 358 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.

Top guest favorite
A bright bedroom features a comfortable double bed with decorative cushions arranged on top. Two neatly rolled towels are placed on the bed. A wooden bedside table with a lamp stands next to the bed, while floral wallpaper and a decorative mirror enhance the space.
Apartment in Henleaze
4.92 out of 5 average rating, 299 reviews

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

Guest favorite
A bright sleeping area features a spacious bed dressed in white linens, accented by decorative pillows. A nightstand with a lamp is positioned beside the bed. Large windows allow natural light to stream in, with sheer curtains partially obscuring the view.
Condo in Henleaze
4.94 out of 5 average rating, 124 reviews

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

When is the best time to visit Cheltenham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,422 GYDG$37,213 GYDG$60,210 GYDG$40,140 GYDG$42,231 GYDG$42,649 GYDG$41,185 GYDG$42,231 GYDG$40,767 GYDG$41,394 GYDG$43,903 GYDG$42,022 GYD
Avg. temp5°C5°C7°C9°C12°C15°C18°C17°C15°C11°C7°C5°C

Quick stats about vacation rentals that are family-friendly in Cheltenham

  • Total vacation rentals

    Explore 750 vacation rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham vacation rentals start at G$6,272 GYD per night before taxes and fees

  • Verified guest reviews

    Over 25,040 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 190 rentals that welcome pets

  • Rentals with dedicated workspaces

    290 properties have a dedicated workspace

  • Wi-Fi availability

    740 of Cheltenham vacation rentals include wi-fi 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