Family-friendly vacation 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.

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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, 365 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 well-appointed studio space features a double bed adorned with yellow and teal cushions, complemented by a cozy sofa. Natural light filters through frosted glass doors, leading to the outdoor area. Soft grey walls and wooden flooring enhance the room's tranquil atmosphere.
Guest suite in Henleaze
4.88 out of 5 average rating, 101 reviews

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.

Top guest favorite
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.
Apartment in Henleaze
4.86 out of 5 average rating, 117 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 favorite
A colorful armchair with patchwork fabric is positioned beside a slender lamp, creating a cozy reading nook. A tall window allows natural light to illuminate the space, complemented by light sheer curtains. A small side table and decorative elements add charm to the inviting room.
Apartment in Henleaze
4.88 out of 5 average rating, 190 reviews

Stunning Regency flat with parking town centre

This Beautiful Regency 1 bed apartment with 1 parking spot (available from 4pm check in to 12 noon check out please) is suitable for adults only. House is situated within walking distance of Cheltenham racecourse, all shops, parks, restaurants and theatres. It has been recently been refurbished . Lovely new carpets and furniture throughout…. Sitting room, kitchen are on one floor with a fabulous double bedroom and a lovely luxury bathroom with shower and large bath tub on the top floor.

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, 751 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.

Top 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, 126 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, 133 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, 157 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.

Guest favorite
A modern living room features a comfortable white leather sectional sofa, facing a large wall-mounted television. A sleek coffee table is placed on a soft black rug, complemented by a stylish floor lamp. Natural light streams in through large windows, framed with patterned curtains.
Condo in Henleaze
4.91 out of 5 average rating, 160 reviews

Beautiful & Vast Central Apartment Free Parking

Welcome to my spacious apartment within Montpellier! This exceptional ground floor living space offers a comfortable and inviting atmosphere, providing you with the perfect place to call home. Located in a desirable neighborhood, this apartment is conveniently situated close to a variety of dining, shopping, and entertainment options. With easy access to major transportation routes, you'll have no trouble exploring the surrounding area and beyond

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, 376 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
4.93 out of 5 average rating, 307 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 spacious room features a comfortable king-size bed covered with a textured yellow quilt. A kitchenette is visible in the background, alongside a wooden table. Natural light enters from a nearby window, illuminating the simple decor, which includes a dresser and casual seating.
Guest suite in Henleaze
4.88 out of 5 average rating, 372 reviews

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

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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 ﺩ.ﺇ110 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

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