Family-friendly holiday rentals in Cheltenham

4.93 out of 5 average rating, 557 reviews

A wide view of rolling green hills displays a tranquil landscape. A small pond is nestled among lush foliage, surrounded by paths cutting through the greenery. Trees are scattered throughout the scene, contributing to the natural beauty of the area.

Cottage in Winchcombe

The Bothy cottage in the Cotswolds

The Bothy is a conversion of a 17th Century Cotswold stone stable and a 20th Century kennel building. On the ground floor is the living room with a beautiful wood burning stove, a fully equipped kitchen, a comfortable double bedroom and a modern shower room. Whilst upstairs, which is accessed from a narrow oak staircase, you can find the twin bedroom. The living room has been fitted to retain all its original features and is furnished in period style. I have included many Georgian and Victorian pieces and have also included a large settee and two arm chairs, dining table and chairs for 4, corner cupboard and a dash of the 21st Century with a Sky television. The Bothy is beautifully situated in the Postlip Coombe on the leeward side of the Cotswolds highest hill and yet only minutes from Winchcombe, a classic Cotswold "wool" town, renowned for its excellent shops, restaurants and architecture.

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, 233 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.

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, 320 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.

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.

4.84 out of 5 average rating, 195 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).

Guest suite in Cheltenham

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.

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.

4.99 out of 5 average rating, 178 reviews

The living room features a prominent chandelier and an original fireplace, accented by a large mirror above it. A cozy leather sofa and a patterned rug complement the space, which includes a large dining table set for six. Tall windows with original shutters allow natural light to fill the room.

4.93 out of 5 average rating, 101 reviews

21A Montpellier Terrace: Location and Luxury

21A, the upper maisonette at 21 Montpellier Terrace has been described by guests as the perfect location in Cheltenham. Barely 100 yards from The IVY and Montpellier restaurants and across from Montpellier gardens. Built in 1835, 21A has gorgeous period features combined with a luxurious remodel. High quality furniture, bathrooms and and TV's in every bedroom. Sorry but this home is not suitable for children. Please contact me before booking if you would like to book with children.

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, 417 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.

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, 147 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.

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

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, 174 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

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, 171 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.

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.

Popular amenities for Cheltenham family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 197 reviews

Home in Boddington

Boddington Mill

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, 198 reviews

Central penthouse with private hot tub and views

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.

4.9 out of 5 average rating, 154 reviews

Town Centre Penthouse with Hot Tub 22

4.89 out of 5 average rating, 111 reviews

Stunning Five Bed Detached Home with Hot Tub

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, 110 reviews

Traditional 6br farmhouse

4.96 out of 5 average rating, 175 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

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, 123 reviews

Chic Georgian Townhouse in Cheltenham

5.0 out of 5 average rating, 193 reviews

The exterior of a Georgian house features a white facade with large windows and a welcoming entrance. A paved pathway leads to the front door, flanked by vibrant flower beds filled with blooming roses and other colorful plants, enhancing the serene ambiance.

Home in Tewkesbury

Attractive Period House with breath-taking views

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

4.91 out of 5 average rating, 688 reviews

4.87 out of 5 average rating, 133 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.

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, 188 reviews

Pittville Loft - 5* Free parking no cleaning fee

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

A living area features a comfortable blue sofa adorned with patterned pillows. A wooden coffee table sits in the center, complemented by a potted orchid. A dining space with bar stools and wall art is visible in the background, along with natural light entering through large windows.

4.98 out of 5 average rating, 104 reviews

New for Cheltenham Festival

4.94 out of 5 average rating, 176 reviews

The entrance to the stables features a modern grey door with a welcoming sign. A brick pathway leads to the entrance, flanked by wooden support beams and lush greenery, creating an inviting approach to the accommodation.

Cottage in Cheltenham

The Stables - Luxury Central Cheltenham Bolthole

A serene bedroom features a spacious bed with neutral-toned bedding and decorative cushions. Artwork adorns the wall above the bed. A large mirror reflects the room's decor. Natural light filters through the window, while a desk and stylish chair occupy one corner.

4.78 out of 5 average rating, 160 reviews

Hermitage Cottage

4.98 out of 5 average rating, 271 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

Family-friendly home rentals with a pool

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.

4.91 out of 5 average rating, 388 reviews

Stunning flat with swimming pool, garden, parking

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

4.93 out of 5 average rating, 146 reviews

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

Condo in Chedworth, Cheltenham

Cosy, rural apartment with breakfast hamper

4.93 out of 5 average rating, 398 reviews

4.97 out of 5 average rating, 149 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

4.89 out of 5 average rating, 177 reviews

Home in Somerford Keynes

43 Clearwater - family gatherings + pools + lakes

Cottage in Somerford Keynes

The exterior of the cottage showcases a unique round tower with a thatched roof, surrounded by lush greenery. Soft evening light casts gentle shadows on the textured stone walls, enhancing the natural setting. The property is framed by trees and greenery, providing a serene atmosphere.

Riverbank House (spa, lakes, tennis & more)

4.93 out of 5 average rating, 193 reviews