Family-friendly holiday rentals in Cheltenham

5 out of 5 average rating, 304 reviews

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.

Home in Cheltenham

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, 386 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.

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, 174 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.

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, 169 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.

4.99 out of 5 average rating, 165 reviews

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.

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, 367 reviews

Stunning Regency Retreat; pool, garden and 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.

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, 383 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.

4.96 out of 5 average rating, 191 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.

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, 262 reviews

Montrose Lodge Regency Apartment, free parking(x2)

A beautifully refurbished Regency-style apartment in a superb central location. With permit street parking included for 2 vehicles within zone 1, extended parking times are available on request. The accommodation has been renovated to a high standard, featuring high ceilings, elegant period detailing, and a spacious, light-filled interior. Just a short walk to Montpellier and the Imperial Gardens, the perfect base to explore wonderful Cheltenham and all it has to offer.

Guest house 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.

4.91 out of 5 average rating, 402 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.

A comfortable bedroom is highlighted by a spacious bed with a light-grey headboard. Decorative pillows add texture. Two bedside lamps provide soft illumination. Artwork featuring a tree and Cheltenham-themed prints adorn the walls, contributing to a cozy and inviting ambiance.

4.91 out of 5 average rating, 248 reviews

Stylish apartment in the heart of Cheltenham

A chic stylish one bedroom apartment in a Victorian townhouse in the centre of Cheltenham with FREE PARKING. Perfectly located to experience all Cheltenham has to offer. A short walking distance to festival locations and the most popular bars and restaurants in Montpellier, The Suffolks, Bath Road and the Promenade. The racecourse is a 25 minute walk or 10 minutes by road. An ideal base for those travelling for business or pleasure.

4.94 out of 5 average rating, 189 reviews

A cozy bedroom features a spacious bed with a gray headboard, complemented by a quilted bedspread and plaid throw pillows. Decorated walls showcase framed artworks, and natural light enters through a nearby window, which is adorned with a fabric blind.

Home in Cheltenham

Central Cosy Terraced Victorian 2 Bedroom Cottage

Enjoy easy access to everything from this perfectly located cottage. Set in the heart of Cheltenham, the property is ideally located to access all the Town has to offer. Within walking distance of the Town Centre, The Suffolks, Montpellier and Bath Road this is perfectly situated for shopping, dining and exploring. A perfect base for business guests or those wishing to explore Cheltenham and The Cotswolds.

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 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

4.9 out of 5 average rating, 331 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!

4.99 out of 5 average rating, 193 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

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, 144 reviews

Town Centre Penthouse with Hot Tub 22

4.96 out of 5 average rating, 138 reviews

The exterior of a cozy pod is displayed, featuring a welcoming entrance with double doors. A wooden deck leads to the main door, complemented by outdoor seating and a barbecue. Surrounding greenery enhances the natural setting, providing an inviting atmosphere.

Cabin in Whitfield

Cosy Bluebell Pod - Eastwood Glamping

4.93 out of 5 average rating, 286 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

5 out of 5 average rating, 288 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

Shepherd’s hut in The Camp

A cozy interior showcases a spacious bed with ample pillows, adjacent to a small table and chairs. A woven rug adds texture to the wooden floor. Natural light enters through two windows adorned with green blinds, while decorative elements, including a basket and vibrant flowers, enhance the inviting atmosphere.

4.84 out of 5 average rating, 239 reviews

Foston's Ash Shepherd's Hut (Lawlessdown:blue hut)

Family- and pet-friendly home rentals

Guest house 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.

4.92 out of 5 average rating, 657 reviews

Cotswold lodge with amazing views and famous walks

Guest house in Cheltenham

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.

4.93 out of 5 average rating, 109 reviews

Prestbury Village Annex.

4.94 out of 5 average rating, 202 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

4.93 out of 5 average rating, 169 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 charming wooden building is visible, featuring a steeply pitched roof and multiple gabled windows. Two vehicles are parked in front on a gravel driveway, framed by a natural stone wall and lush greenery in the background.

5 out of 5 average rating, 138 reviews

Stunning Apartment located on the Cotswold Way

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, 186 reviews

Town Centre Apartment with Hot Tub

Guest house 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, 169 reviews

Chapel End

4.99 out of 5 average rating, 147 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

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 146 reviews

Home in Nailsworth

40% off June Weekends. Private Heated Pool.

4.98 out of 5 average rating, 440 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

4.84 out of 5 average rating, 100 reviews

A private hot tub with gently bubbling water is positioned next to a cozy corner sofa covered with soft cushions. A small table is placed in front of the seating area. The surrounding decking features a serene setting with lush greenery and a partly cloudy sky.

Chalet in South Cerney

Burford Hot tub Lodge, Free Hoburne Passes

4.94 out of 5 average rating, 126 reviews

Home in Somerford Keynes

Lakeside | Hot Tub | Pools & Spa | Lower Mill E

4.98 out of 5 average rating, 140 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

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, 135 reviews

The Ndoro Carriage with use of A Natural Pool.

4.98 out of 5 average rating, 312 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