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.

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.

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 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).

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, 180 reviews

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.

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 😁

4.95 out of 5 average rating, 112 reviews

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

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.

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.

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.

4.92 out of 5 average rating, 423 reviews

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, 245 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.

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.

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

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

4.89 out of 5 average rating, 113 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, 111 reviews

Traditional 6br farmhouse

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

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!

4.9 out of 5 average rating, 172 reviews

A spacious outdoor patio area is featured, furnished with a large dining table and several chairs. The brick structure showcases expansive glass doors that invite natural light, with a green lawn extending towards the unspoiled countryside beyond.

Farm stay in Kempley

Luxury accommodation in stunning setting sleeps 16

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

4.94 out of 5 average rating, 102 reviews

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

4.92 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

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

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)

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.

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

4.94 out of 5 average rating, 179 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 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

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.

Hyde Mill Cottage

4.97 out of 5 average rating, 103 reviews

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, 149 reviews

Condo in Chedworth, Cheltenham

Cosy, rural apartment with breakfast hamper

4.93 out of 5 average rating, 404 reviews

4.98 out of 5 average rating, 454 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

4.97 out of 5 average rating, 152 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