Family-friendly holiday rentals in Cheltenham

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.

4.98 out of 5 average rating, 236 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.

Indoor spacesKitchenOutdoor spaces

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.

5.0 out of 5 average rating, 323 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.

FamilyIndoor spacesAmenities

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.

4.87 out of 5 average rating, 404 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.

FamilyIndoor spacesComfort

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.

4.85 out of 5 average rating, 200 reviews

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).

KitchenFamilyCheck-in

The exterior of a large Regency villa is presented, showcasing its elegant white façade and grand entrance steps. Lush greenery surrounds the building, with trees and well-kept shrubs enhancing the tranquil setting. A private parking area is visible in the foreground.

4.92 out of 5 average rating, 390 reviews

Stunning flat with swimming pool, garden, 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.

FamilyIndoor spacesCondition

A cozy living room is presented with light-colored furnishings. A plush sofa complements the wooden coffee table, while a flat-screen TV sits to one side. The room is illuminated by natural light from the window, adorned with soft drapes, and features a decorative fireplace.

4.95 out of 5 average rating, 419 reviews

MontpellierCourtyard Apt,parking for 1 car.Sleeps4

Our courtyard apartment is set right in the heart of beautiful Regency Montpellier. Home to countless restaurants, bars and boutiques, there is something for everyone. Located directly behind the vibrant Suffolk Parade, with its eclectic mix of Independent shops, galleries and bars. It's a 2 minute walk to Montpellier Gardens, home of some of the Festivals that Cheltenham is renowned for. Imminently approaching is The Food & Drink Festival, followed by The Jazz Festival in early July.

KitchenIndoor spacesCheck-in

Guest suite in Cheltenham

The interior of the annexe showcases two single beds dressed in a patterned bedspread. A compact kitchen area is visible, equipped with essential appliances. A small dining space is positioned near a window, which allows natural light to illuminate the room. A wall-mounted TV is also present.

Self contained Annexe in quiet area

Come and enjoy a stay in a quiet cul de sac 5/10 min walk from Cheltenham train station, 5 min drive from M5/GCHQ- within walking distance of Cheltenham Town center and Montpellier. Newly built self contained annexe with private entrance within our family home. Modern kitchen and ensuite with multiple bed configurations to suit up to 2 guests. Free parking around the cul de sac and WiFi included. Extensive knowledge of the local area, if we can be of any assistance do let us know 😁

KitchenIndoor spacesLocation

4.95 out of 5 average rating, 112 reviews

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.

4.87 out of 5 average rating, 149 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.

Indoor spacesFamilyNearby

A spacious sitting room featuring a fireplace and a large mirror reflecting natural light. Elegant furnishings include a comfortable sofa, a coffee table, and a decorative chandelier overhead. A wooden desk and chair provide a functional workspace, complemented by gentle tones and soft textures throughout.

4.98 out of 5 average rating, 120 reviews

Georgian townhouse in famous Suffolks area

A unique opportunity to stay in a beautiful Grade 2 listed Georgian townhouse in the famous Suffolks area of central Cheltenham with four bedrooms and six beds. Easy walking distance to all amenities, bistros and restaurants (5 min), Montpellier, the Promenade shops and Bath Road (10 min), racecourse (40 min), Cricket festival (5 min) and Literature, Jazz, Music and Science festivals (5 min). Perfect for Race Week, and a great base for touring the Cotswolds. Free parking nearby

Indoor spacesFamilySleep quality

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.

4.94 out of 5 average rating, 175 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

Indoor spacesKitchenOutdoor spaces

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.

4.95 out of 5 average rating, 176 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.

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4.99 out of 5 average rating, 578 reviews

Beautiful Two Bedroom Apartment

A spacious, 1000 sq ft / 92 sqm, two double bedroom apartment, taking up the entire lower ground floor of a beautiful Grade II listed Villa in central Cheltenham. Self contained, it has its own entrance, two bedrooms, a separate kitchen, separate sitting room, and bathroom with shower. It also has super fast 150mb wifi broadband.

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Popular amenities for Cheltenham family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 199 reviews

Home in Boddington

Boddington Mill

FamilyKitchenEV charging

A bright living area showcases a neutral-toned sofa, complemented by decorative pillows. A coffee table adorned with a floral arrangement sits in front of a ornate fireplace, flanked by elegant lamps. Mirrors with arches reflect natural light, enhancing the room's serene ambiance.

4.73 out of 5 average rating, 124 reviews

Chic Georgian Townhouse in Cheltenham

KitchenFamilyAmenities

A private hot tub is situated on a rooftop terrace, surrounded by a neatly arranged seating area. The tub invites relaxation while offering panoramic views of Cheltenham's skyline and spires under a cloudy sky.

4.93 out of 5 average rating, 200 reviews

Central penthouse with private hot tub and views

KitchenFamilyAmenities

4.89 out of 5 average rating, 113 reviews

Stunning Five Bed Detached Home with Hot Tub

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The traditional farmhouse is depicted from the exterior, showcasing its stone façade and distinctive architecture. A well-maintained garden is visible in the foreground, while the blue sky and scattered clouds complement the overall setting.

4.85 out of 5 average rating, 111 reviews

Traditional 6br farmhouse

KitchenIndoor spacesQuiet

4.96 out of 5 average rating, 180 reviews

A charming stone cottage stands proudly under a clear blue sky, featuring a symmetrical facade with white-framed windows. A neatly landscaped garden with low hedges and shrubs frames the entrance, while a path leads to the front door.

Home in Winchcombe

Luxury Cotswolds Cottage with Hot Tub

KitchenIndoor spacesAccess

4.9 out of 5 average rating, 378 reviews

A modern cabin exterior is illuminated by soft lighting, complemented by wooden paneling for a rustic touch. A private heated hot tub is visible nearby, surrounded by a peaceful garden. The image also features a rustic barrel, adding character to the outdoor space.

Cabin in Cheltenham

Luxury Cabin with Hot-Tub & Cold Plunge!

FamilyIndoor spacesHiking

4.93 out of 5 average rating, 304 reviews

The exterior of a charming cottage is featured, showcasing a combination of modern and traditional elements. Black timber beams contrast with whitewashed walls. A gravel pathway leads to the entrance, framed by potted plants. A fenced area is visible to the right, adding to the property's privacy.

Cottage in Ashleworth

Rural, character 2 bed cottage and hot tub

FamilyIndoor spacesGetting around

Family- and pet-friendly home rentals

Guesthouse in Gloucestershire

The lodge is viewed from a wooden gate, framed by trees. The structure features large glass windows, revealing a bright and open design. Rolling hills can be seen in the distance under a clear blue sky.

Luxury Cotswold Lodge |Stunning View of Cheltenham

Indoor spacesFamilyValue

4.92 out of 5 average rating, 695 reviews

The reception room features high ceilings and two large sash windows that provide natural light. A stylish sofa bed and a vibrant armchair are arranged around a flat screen TV. A decorative fireplace adds character, complemented by plants and tasteful wall art.

4.9 out of 5 average rating, 260 reviews

Clarence Square Penthouse

Indoor spacesFamilyNearby

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.

4.93 out of 5 average rating, 195 reviews

Pittville Loft - 5* Free parking no cleaning fee

FamilyKitchenComfort

A seating area is furnished with a dark grey sofa and wooden coffee table, positioned on a patterned rug. Four dining chairs surround a wooden dining table. Light streams through two windows, complemented by burgundy curtains. A wall-mounted television is installed above the decorative media unit.

4.96 out of 5 average rating, 290 reviews

Montrose Lodge Regency Apartment, free parking(x2)

FamilyIndoor spacesValue

4.87 out of 5 average rating, 136 reviews

A pathway lined with lush greenery leads to a charming dwelling partially hidden by trees and bushes. The gravel drive is framed by manicured hedges, creating a serene entrance. Natural light filters through the foliage, highlighting the tranquil setting of the home.

Guesthouse in Cheltenham

Prestbury Village Annex.

Indoor spacesKitchenSleep quality

A dining area is shown with a round table surrounded by two wooden chairs and a bench. A vintage blue refrigerator stands nearby. Natural light fills the space through a large window, revealing a staircase outside. A bowl and wine glasses are placed on the table, enhancing the inviting setting.

4.98 out of 5 average rating, 281 reviews

Townhouse luxury, central Grade 2 listed apartment

Indoor spacesFamilyWalkability

4.98 out of 5 average rating, 275 reviews

The exterior of Wycke Cottage features charming stone walls adorned with lush green vines. Multiple windows allow natural light to fill the space, while potted plants in various sizes enhance the entrance. A clear blue sky creates a serene backdrop.

Home in Painswick

Cottage luxe in The Cotwolds

KitchenIndoor spacesComfort

4.94 out of 5 average rating, 215 reviews

An open plan master bedroom is illuminated by natural light from large windows. A free-standing roll-top bath sits beside the bed, accompanied by a potted plant. Exposed wooden beams add character, while tasteful wall art complements the tranquil decor.

Cottage in Prestbury

Luxury Thatched Cotswold Cottage, amazing location

Indoor spacesKitchenGetting around

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 175 reviews

A large swimming pool is surrounded by a stone patio, featuring four sun loungers and an umbrella for shade. The serene setting includes a wall of greenery and views of the Georgian Manor House in the background, illuminated by bright sunlight.

Home in Bredon

Cotswolds Cottage, Heated Pool, Tithe Barn Views

Indoor spacesKitchenAccuracy

Cottage in Somerford Keynes

The cottage's spacious sundeck features an outdoor dining setup with a table and chairs, alongside a charcoal BBQ. French doors lead inside, illuminating the space as the sun sets over the lush greenery. A simple umbrella provides shade, enhancing the outdoor experience.

Cornerstone Cottage a/c LowerMillEstate Cotswolds

FamilyKitchenAccess

4.93 out of 5 average rating, 149 reviews

Condo in Chedworth, Cheltenham

Cosy, rural apartment with breakfast hamper

KitchenIndoor spacesWalkability

4.93 out of 5 average rating, 404 reviews

Cottage in Stow-on-the-Wold

A charming stone cottage with a steeply pitched roof is framed by lush greenery. The exterior features multiple windows that allow natural light, and a wooden gate leads into a pebbled driveway. The grassy area surrounds the cottage, accentuating its tranquil setting.

Hyde Mill Cottage

KitchenIndoor spacesLayout

4.97 out of 5 average rating, 103 reviews

Cottage in Little Comberton

An indoor swimming pool is featured under arched windows, allowing natural light to illuminate the space. Comfortable seating is arranged alongside the pool, and the tranquil water reflects the elegant architecture of the room.

Well Furlong Cotswold Cottage, pool & hot tub

Indoor spacesFamilyLocation

4.94 out of 5 average rating, 102 reviews

4.98 out of 5 average rating, 455 reviews

A spacious bedroom features original lime-washed oak beams and Cotswold stone walls. A king-sized bed dressed with elegant linens is complemented by two bedside tables with matching lamps. A conservation window allows natural light and offers a view of the outside garden.

Cottage in Cirencester

The Potting Shed, 5* ❤︎ Luxury escape Cirencester

FamilyKitchenOutdoor spaces

4.94 out of 5 average rating, 141 reviews

Home in Somerford Keynes

Lakeside/Hot Tub/Jetty/Pools/Spa/Lower Mill Estate

Indoor spacesFamilyCheck-in