House holiday rentals in Cheltenham

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Top-rated house rentals in Cheltenham

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
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
5 out of 5 average rating, 297 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.

Guest favourite
Home in Boddington
4.95 out of 5 average rating, 181 reviews

Boddington Mill

Boddington Mill is a stunning countryside retreat in the heart of the Cotswolds, steeped in history and rural charm. The building retains industrial mill parts which intersect multiple levels for a unique and generous living space. Its south-facing garden includes outside dining, wood-fired hot tub, and large lawn, home to wildlife and fruit-bearing trees. Inside, the three king sized bedrooms feature luxury bedding beneath vaulted, oak-beamed ceilings and period windows. Sky TV, Sonos speakers.

Guest favourite
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.
Home in Cheltenham
4.79 out of 5 average rating, 135 reviews

Hermitage Cottage

Out Serviced Ltd is proud to present Hermitage Cottage. A cosy house located just off the vibrant and famous Bath Road. The property comprises a living area, a kitchen/diner, bathroom with shower over bath, a ground floor bedroom with a king size bed, a double bedroom and a small single room. There is also a small courtyard with seating for some outdoor space. Parking is free 'on street' parking on Hermitage Street or surrounding roads. There is also a pay and display car park on Bath Terrace

Guest favourite
A well-appointed bedroom features a spacious bed dressed in crisp white linens, accompanied by a textured grey throw. Two windows allow natural light to illuminate the room, while a minimalistic chair and a mirrored wardrobe enhance the sense of space.
Home in Cheltenham
4.86 out of 5 average rating, 105 reviews

5 Bed House, Sleeps 8, parking, brilliant location

Cheltenham Town Centre 5 Bedroom House with Courtyard Garden. Ideally located next to the Brewery Quarter in the town centre, within easy walking distance to the racecourse, our modern, well equipped functional property is ideal for families or groups looking to explore Cheltenham. There are 5 bedrooms (not 4 and a sofa bed!) with 3 double (1 with en suite) and 2 single bedrooms - 5 bedrooms in total - sleeping up to 8 people. Parking on site for 1 small/medium car/paid carpark 3 minute walk.

Guest favourite
Home in Painswick
4.94 out of 5 average rating, 161 reviews

Peaceful Cotswolds Chapel Breathtaking 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.

Top guest favourite
Home in Cheltenham
4.97 out of 5 average rating, 100 reviews

Self contained Annex in Montpellier with parking

The Annex is completely Self-Contained with Stylish Interior, unique architecturally designed property in the heart of the Suffolks. This is a vibrant area with excellent restaurants, bars and boutique shops, ideal for Cheltenham's festivals. Access is via private courtyard. Downstairs is open plan, living area with TV, kitchen, breakfast bar, dining and John Lewis sofa bed comfortable for extra two guests to sleep. Upstairs is a large bedroom with king size bed and en-suite shower room.

Top guest favourite
The exterior of the larch clad Annexe features modern vertical wood paneling. Large glass doors lead into the entrance, framed by two planters with lush green grass. A gravel path provides access, highlighting the contemporary architecture amid a clear blue sky.
Home in Cirencester
4.98 out of 5 average rating, 251 reviews

Larch clad architect designed contemporary annexe.

Relax at this unique and tranquil getaway in the beautiful South Cotswolds. The Annexe is a separate dwelling next to an architecturally award winning contemporary house located in a quiet village. The larch clad property has an industrial, boho meets the Cotswold vibe with its own private wild flower garden, perfect for alfresco dining. Excellent location for walking, running and cycling. Close to the beautiful town of Cirencester, idyllic picturesque villages and gastro pubs galore!

Top guest favourite
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.
Home in Cheltenham
4.97 out of 5 average rating, 112 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

Top guest favourite
The charming Cotswold stone cottage is framed by lush greenery and colorful flowers. A gravel pathway leads to the entrance, flanked by a small pond. The property features a symmetrical facade, with multiple gabled roofs and large windows reflecting natural light.
Home in Coberley
4.93 out of 5 average rating, 326 reviews

Beautiful Cotswold Stone Cottage

Situated close to the Cotswold Way and the Gloucestershire Way footpaths, Close Cottage (the earliest building in Coberley circa 1550) really is in the heart of the Cotswold Hills. The self contained property comprises: two double bedrooms, fully equipped kitchen, shower room and a cosy lounge with wood burner. The traditional Cotswold stone cottage overlooks picturesque countryside and is situated within ten minutes drive from the beautiful and popular spa town of Cheltenham.

Top guest favourite
The exterior of the property features a charming brick facade, complemented by multiple windows that allow natural light to fill the interior. A covered entrance leads to the home, while wooden storage units provide practical outdoor space on the side.
Home in Cheltenham
4.98 out of 5 average rating, 198 reviews

7 Diamond Jubilee, Cheltenham

Diamond Jubilee is a unique fully electric property located in a quiet little mews street but a short walk to the bars, shops, and restaurants of the vibrant area of The Suffolks and Montpellier. Cheltenham has a thriving cultural scene and hosts numerous festivals throughout the year such as the jazz, food and drink, literature, and science. Undoubtedly, the highlight of the year is the annual racing festival, The Gold Cup at Cheltenham Racecourse. Newly renovated bathroom.

Top guest favourite
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
5 out of 5 average rating, 281 reviews

Magical cottage set within a woodland glade

Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

Top guest favourite
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
4.98 out of 5 average rating, 199 reviews

Cottage luxe in The Cotwolds

Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Popular amenities for house rentals in Cheltenham

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Quick stats about house rentals in Cheltenham

  • Total holiday rentals

    Explore 820 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 20,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    480 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wifi availability

    810 of Cheltenham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cheltenham rentals

  • 4.9 Average rating

    Cheltenham stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Cheltenham’s top spots include Cheltenham Racecourse, Pittville Park and Everyman Theatre

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