Family-friendly vacation 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, 317 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.

FamilyIndoor spacesGetting around

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.

FamilyKitchenComfort

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, 188 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).

KitchenFamilyNearby

4.94 out of 5 average rating, 179 reviews

Home in Painswick

Breathtaking Cotswolds Restored Chapel Valley View

Step into a rare and remarkable stay at ‘The Old Church’, a lovingly restored & renovated 1820s chapel nestled on the hillside in the idyllic Cotswolds village of Sheepscombe. This enchanting property blends timeless character & period charm with a relaxing contemporary feel. A truly unique picturesque countryside escape. Located in a tranquil woodland setting on the edge of Blackstable Nature Reserve with scenic valley walks, a rustic village setting, a playground & lovely pub down the lane.

KitchenIndoor spacesView

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, 279 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.

KitchenFamilyLaundry

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, 409 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.

Indoor spacesFamilyValue

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, 100 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.

FamilyKitchenWifi

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.

Indoor spacesFamilyDecor

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.

Indoor spacesKitchenBathroom

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, 169 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.

KitchenFamilyDecor

4.94 out of 5 average rating, 173 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

Gorgeous converted stables located in the heart of Cheltenham originally belonging to a Georgian Villa, this is the ideal place to stay for a long weekend or mid week break in the Cotswolds. Perfectly located within walking distance of the bars and restaurants of the Suffolk's and Montpellier, and all that Cheltenham has to offer, be that one of the many the festivals or of course the races .

Indoor spacesFamilyAccuracy

A spacious living area is depicted, featuring a cozy white sofa adorned with dark cushions. A wooden coffee table sits in front, showcasing magazines. Natural light floods the room through a large arched window, offering views of greenery outside, complemented by soft wall lights.

4.97 out of 5 average rating, 151 reviews

Regency apartment in the centre of Cheltenham.

Beautiful newly refurbished ground floor flat within a large regency town house in Clarence Square situated in walking distance to Cheltenham town centre and the famous Cheltenham Racecourse. The flat has one bedroom, wet room, large kitchen and living space. Free on street parking is available on request, we will need your registration number prior to your arrival to book this.

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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 spacesFamilyOutdoor spaces

4.94 out of 5 average rating, 193 reviews

Home in Boddington

Boddington Mill

FamilyIndoor spacesAccuracy

4.89 out of 5 average rating, 361 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!

FamilyKitchenDecor

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

FamilyKitchenLong stay

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 spacesKitchenHospitality

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

KitchenIndoor spacesAccess

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 spacesPets

4.97 out of 5 average rating, 289 reviews

A private patio area features a round wooden table with four folding chairs, surrounded by colorful flowers. A wood-fired hot tub is visible nearby, overlooking a scenic view of lush hills and greenery, under a bright sky with scattered clouds.

Cottage in Mitcheldean

Romantic Idyllic Nuthatch Cottage with Hot Tub

KitchenIndoor spacesBreakfast

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

Indoor spacesFamilyWalkability

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 spacesParking

4.94 out of 5 average rating, 210 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

FamilyIndoor spacesDecor

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, 99 reviews

New for Cheltenham Festival

Indoor spacesFamilyBackyard

4.98 out of 5 average rating, 258 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

KitchenIndoor spacesGetting around

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

KitchenIndoor spacesValue

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

Indoor spacesFamilyAccess

Bungalow in Gloucestershire

A bright living area features a grey sofa and armchair, with a coordinating ottoman in the center. Natural light floods through large windows that overlook the private garden. A dining table for four sits nearby, and a TV unit offers entertainment options.

5 out of 5 average rating, 104 reviews

Cosy dog friendly self contained Annexe

KitchenIndoor spacesCheckout

Family-friendly home rentals with a pool

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

FamilyKitchenQuiet

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

KitchenIndoor spacesValue

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

FamilyKitchenShared spaces

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

Indoor spacesFamilyOutdoor spaces

4.98 out of 5 average rating, 320 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

FamilyIndoor spacesLaundry

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.

Indoor spacesFamilyHeating

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, 100 reviews

Hyde Mill Cottage

FamilyKitchenNearby