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, 234 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, 321 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 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.

A spacious bedroom is highlighted by a large, comfortable bed with a soft, white duvet. Two windows allow natural light to fill the room, and rolled towels are neatly arranged on the bed. A wooden dresser and a small rug complete the inviting space.

4.9 out of 5 average rating, 100 reviews

Central 2 Bed Apt | Free Parking | No Cleaning Fee

Modern, large 2 bedroom town centre apartment set in an exclusive gated development with allocated parking for 1 small car (up to mid-size SUV - no vans or long vehicles). Secure access and fibre broadband. Step-free entry using lift. Early check-in may be possible. Not child safe but welcome at own risk. Sorry, no pets due to building rules. This is my home, not a full-time rental, meaning you get to enjoy comforts like good showers and quality furnishings. Please respect my personal effects.

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).

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, 102 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, 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.

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, 148 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

The entrance of a historical building showcases a bright yellow door flanked by decorative wrought iron balconies. Potted plants are positioned on either side of the entrance, complementing the stone facade. Steps lead to the front door, framed by classic wrought iron fencing.

4.95 out of 5 average rating, 169 reviews

Regency flat, private courtyard, free parking

A beautiful recently renovated Regency flat in a grade II* building. We are 5 minutes walk to the city centre and 25 minutes to the Racecourse. The flat has its own front door and private courtyard. Virgin VIP package and high speed broadband plus Sky & BT Sports. One kingsize bed with soft linen sheets, plus one sofa bed for additional guests (book for 3 if you want the sofa bed). Well equipped kitchen. Separate shower room (off living room). Free parking nearby. Nest heating.

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, 174 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 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.

4.92 out of 5 average rating, 335 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

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

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

4.94 out of 5 average rating, 198 reviews

Home in Boddington

Boddington Mill

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

4.96 out of 5 average rating, 176 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

4.89 out of 5 average rating, 111 reviews

Stunning Five Bed Detached Home with Hot Tub

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

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

4.93 out of 5 average rating, 320 reviews

Home in South Cerney

Grebe Lodge | Cotswold Lakehouse & Hot Tub, Kayaks

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, 692 reviews

Luxury Cotswold Lodge |Stunning View of Cheltenham

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, 191 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

4.98 out of 5 average rating, 273 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

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, 106 reviews

New for Cheltenham Festival

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, 259 reviews

Clarence Square Penthouse

4.87 out of 5 average rating, 135 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.

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

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.

4.92 out of 5 average rating, 390 reviews

Stunning flat with swimming pool, garden, parking

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

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.

4.97 out of 5 average rating, 101 reviews

Hyde Mill Cottage

Condo in Chedworth, Cheltenham

4.93 out of 5 average rating, 401 reviews

Cosy, rural apartment with breakfast hamper

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.

4.93 out of 5 average rating, 147 reviews

Cornerstone Cottage a/c LowerMillEstate Cotswolds

4.94 out of 5 average rating, 158 reviews

A lakeside home is showcased, featuring large glass windows that offer a view of the water. The exterior is well-lit, reflecting a modern design with a spacious deck. The nearby water reflects the building, contributing to a serene and peaceful environment.

Home in Somerford Keynes

Goosewing - Cotswolds, Lakes, Family, Pools, Spa

4.97 out of 5 average rating, 150 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