Family-friendly holiday rentals in Cheltenham

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 out of 5 average rating, 315 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.

FamilyKitchenWalkability

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, 396 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 spacesHiking

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.

4.94 out of 5 average rating, 185 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.

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, 186 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).

FamilyIndoor spacesParking

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, 275 reviews

Townhouse luxury, central Grade 2 listed apartment

A newly refurbished space respecting the traditional building yet in a contemporary style. Light and airy with small outside courtyard area, and plenty of amenities to make your stay comfortable. Within walking distance of all that Cheltenham has to offer including the racecourse, fabulous restaurants and bars and beautiful parks. Also within striking distance of the stunning Cotswolds. The property is part of our family home yet is completely self contained for your enjoyment and privacy.

FamilyIndoor spacesSleep quality

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, 408 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.

FamilyIndoor spacesTV

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.

4.88 out of 5 average rating, 145 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.

KitchenFamilyAccess

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

KitchenIndoor spacesBathroom

4.97 out of 5 average rating, 204 reviews

A well-appointed bedroom features a king-size bed with a neutral-toned blanket adorned with geometric patterns. A wooden dresser and bedside table provide storage, while a circular mirror above the dresser enhances the sense of space. Soft lamps illuminate the room, creating a relaxed ambiance.

Tiny home in Cheltenham

Studio 77 Cheltenham

You will be very welcome to stay in our brand new and beautifully renovated compact and bijou tiny home which is in an easy walk of Cheltenham Town Centre and the Racecourse. We have created a gorgeous space to the rear of our family home that is completely self contained with its own entrance. Studio 77 comprises of a king size bed, kitchenette area, small seating arrangement and a good sized shower room. There is a small private patio area for guests to enjoy on a sunny evening.

KitchenIndoor spacesParks

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, 167 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.

FamilyKitchenBackyard

Guesthouse in Gloucestershire

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.

4.92 out of 5 average rating, 414 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.

FamilyKitchenCheck-in

A cozy living area features a gray sofa with patterned cushions, positioned beside a modern fireplace. A low coffee table holds fresh fruit, while bookshelves line the walls. Natural light enters through windows covered by blinds, enhancing the bright and inviting space.

4.97 out of 5 average rating, 242 reviews

Self-contained basement flat in regency home

Refurbished basement flat in grade 2 listed regency terraced house. Central Cheltenham location, walking distance to all local festivals, shopping, pubs and restaurants. Modern, light and spacious accommodation with private access and patio terrace via the bedroom. Good size bathroom with bath and walk-in shower. There is no separate kitchen but an area containing a fridge, microwave, kettle & toaster.

KitchenIndoor spacesOutdoor spaces

Popular amenities for Cheltenham family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 121 reviews

Chic Georgian Townhouse in Cheltenham

Indoor spacesKitchenQuiet

4.94 out of 5 average rating, 191 reviews

Home in Boddington

Boddington Mill

Indoor spacesFamilyPets

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.

4.92 out of 5 average rating, 197 reviews

Central penthouse with private hot tub and views

FamilyKitchenNearby

4.99 out of 5 average rating, 201 reviews

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 Thornbury

Lodge farm Woodland dome. Hot tub. luxury escape

Indoor spacesFamilyEV charging

A vase filled with a variety of colorful flowers is positioned in the foreground, near a bubbling hot tub. The background reveals a view of Cheltenham's skyline, with a church tower visible against a clear sky.

4.89 out of 5 average rating, 149 reviews

Town Centre Penthouse with Hot Tub 22

Indoor spacesKitchenGetting around

4.93 out of 5 average rating, 293 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

FamilyKitchenBarbecue

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, 107 reviews

Traditional 6br farmhouse

FamilyIndoor spacesValue

5 out of 5 average rating, 301 reviews

The cottage is set on a hillside, surrounded by lush greenery and trees. A gentle slope leads to the well-maintained garden, with ferns and native plants framing the stone structure. The sky is bright blue with scattered clouds, enhancing the peaceful rural setting.

Home in Amberley

Magical cottage set within a woodland glade

Indoor spacesKitchenTV

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.

4.91 out of 5 average rating, 681 reviews

Luxury Cotswold Lodge |Stunning View of Cheltenham

FamilyIndoor spacesCheckout

4.88 out of 5 average rating, 125 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.

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 207 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

FamilyKitchenSleep quality

4.93 out of 5 average rating, 163 reviews

A comfortable living space features a gray sofa paired with a rustic wooden bench. A stone fireplace with a wood-burning stove is framed by an elegant circular mirror, while warm lighting hangs from the ceiling, creating a cozy ambiance. A television stands on a wooden dresser nearby.

Home in Winchcombe

Beam House, Winchcombe, sleeps 6 + 2

Indoor spacesFamilyNearby

4.98 out of 5 average rating, 257 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

KitchenFamilyValue

A bright sleeping area features a spacious bed adorned with decorative pillows and soft towels. A sliding door opens to a courtyard, revealing a hot tub area framed by bamboo fencing, enhancing the peaceful ambiance of the room.

4.96 out of 5 average rating, 194 reviews

Town Centre Apartment with Hot Tub

FamilyIndoor spacesLayout

Guesthouse in Cleeve Hill

A well-lit two-story living area is shown, featuring a wooden staircase leading to a lofted bedroom. Large skylights above provide natural light. A built-in bookshelf and a television are visible on the lower level, alongside comfortable seating arranged for relaxation.

4.99 out of 5 average rating, 188 reviews

Chapel End

FamilyKitchenComfort

4.99 out of 5 average rating, 155 reviews

The exterior of the converted barn is showcased, featuring rustic red brick walls, a slate roof, and wooden doors. A gravel pathway leads to the entrance, surrounded by greenery and a garden area visible in the background. Skylights are positioned on the roof, allowing natural light.

Barn in Gloucestershire

Beautiful Barn in the Cotswolds

Indoor spacesFamilyBackyard

Family-friendly home rentals with a pool

Holiday home in Somerford Keynes

4.99 out of 5 average rating, 141 reviews

Own Island: Direct Lake Access, Activities, Spa

Indoor spacesFamilyNearby

Cottage in Somerford Keynes

The exterior of Aston Cottage showcases its charming Cotswold stone facade, accented by vibrant garden foliage. Two Juliet balconies provide scenic views. A well-maintained shared pool area is depicted, alongside a dining setup featuring fresh juices and breakfast items, highlighting inviting outdoor leisure.

4.88 out of 5 average rating, 149 reviews

Charming Stone Cotswold Cottage with Pool Access

Indoor spacesFamilyHeating

4.86 out of 5 average rating, 125 reviews

A tranquil scene shows the Dovecote cottage beside a serene lake. Lush greenery frames the water's edge, while flowering trees add a touch of color. The well-maintained garden leads to the cottage, creating a peaceful setting for relaxation.

Cottage in Kemerton

Dovecote Cottage

FamilyKitchenHeating

4.98 out of 5 average rating, 449 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

KitchenFamilyAccess

4.97 out of 5 average rating, 148 reviews

An open-plan space features a large dining table set for six, surrounded by wooden chairs. Natural light streams through expansive windows, providing views of the surrounding landscape. The mezzanine above contains a sofa, and textured stone walls add character to the area.

Home in Gloucestershire

Boundary Court Barn, Selsley common, Stroud

KitchenFamilyLayout

Shepherd’s hut in Lyneham

A cozy kitchenette is shown, featuring pale green cabinetry and open shelving. A bistro table with two chairs occupies one corner, while a comfortable sofa adjoins the space. Natural light filters through a window adorned with charming fabric treatment.

4.99 out of 5 average rating, 144 reviews

The Ndoro Carriage with use of A Natural Pool.

FamilyKitchenAccuracy

4.98 out of 5 average rating, 318 reviews

A tranquil garden scene is displayed, featuring a central pond with a fountain. Surrounding the pond are neatly trimmed hedges and vibrant purple flowers. Lush trees provide shade in the background, contributing to the serene atmosphere of the outdoor space.

Home in Bretforton

Deluxe Coach House at Bretforton Manor with pool

Indoor spacesKitchenParks