Holiday rentals with outdoor seating in Cheltenham

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Cheltenham

Guests agree: These Holiday Houses with Outdoor Seating 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 Henleaze
5 out of 5 average rating, 283 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.

Top Guest favourite
Cottage in Winchcombe
4.98 out of 5 average rating, 210 reviews

Little Nook Cottage - Dog Friendly & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Guest favourite
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 Henleaze
4.96 out of 5 average rating, 169 reviews

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.

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 Henleaze
4.99 out of 5 average rating, 183 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, 264 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
A spacious bed dressed in luxurious linens is accented by two large pillows. Bedside tables with lamps provide soft lighting, while a patterned blind offers privacy. The wooden beams overhead add warmth to the stylish and inviting bedroom environment.
Guesthouse in Withington
5 out of 5 average rating, 471 reviews

Stylish studio apartment with breakfast hamper.

Nestled in the Cotswold countryside, Pillars Loft offers a hideaway perfect for two, with stylish interiors, modern amenities and luxurious home comforts. Bordering the regency spa town of Cheltenham and the charming market town of Cirencester, Pillars is perfectly located for those looking to enjoy a spot of retail therapy, fine dining or festival scene that Cheltenham is renowned for while also catering for those looking for a peaceful rural retreat.

Top Guest favourite
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.
Home in Henleaze
4.96 out of 5 average rating, 140 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.

Guest favourite
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.
Condo in Henleaze
4.91 out of 5 average rating, 235 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.

Top Guest favourite
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.
Apartment in Henleaze
4.98 out of 5 average rating, 223 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.

Guest favourite
A charming flat entrance is showcased, with neatly arranged steps leading up to a black front door framed by white walls. Decorative plants are placed along the pathway, and wrought iron railings complement the classic architectural details of the building.
Apartment in Henleaze
4.8 out of 5 average rating, 293 reviews

Stylish 2 Bedroom apartment in central Cheltenham

A quirky two double bedroom flat based on a quiet, tree lined street. Also available for longer lets. Please get in touch! The flat is based in the centre of Cheltenham, in an ideal location to explore Cheltenham and the surrounding areas. A perfect base for Cheltenham festivals. Please note this apartment is in a very quiet, family friendly neighbourhood and is not suitable for parties.

Guest favourite
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.
Guesthouse in Gloucestershire
4.92 out of 5 average rating, 614 reviews

Cotswold lodge with amazing views and famous walks

Enjoying spectacular views this 2 bedroom, dog friendly lodge sits on the top of Leckhampton Hill, enjoying easy access to the famous ‘Cotswold Way’ walk and is a 5 minute drive from the town centre of regency Cheltenham. The Lodge also includes a 3.5m outdoor kitchen looking over The Malvern Hills. The kitchen includes a large built in BBQ, a pizza oven and sink.

Guest favourite
The modern kitchen features a spacious island with a wood countertop, complemented by grey cabinetry and stainless-steel appliances. Abundant natural light streams through overhead windows, illuminating the open layout. A wall-mounted TV is visible in the background, providing a focal point for the space.
Townhouse in Henleaze
4.86 out of 5 average rating, 286 reviews

Cheltenham Superb 2 Bed Townhouse, The Suffolks

Recently refurbished, Traditionally Modern Townhouse in the Suffolk’s area of Cheltenham ... an area often referred to as the Notting Hill of Cheltenham, with an eclectic mix of independent cafes, bars, restaurants and shops, all on your doorstep Virgin Media SuperFast Fibre Broadband throughout, ideal for streaming and home working purposes.

Popular amenities for Cheltenham outdoor seating rentals

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Quick stats about holiday rentals with outdoor seating in Cheltenham

  • Total holiday rentals

    Explore 380 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $60 AUD per night before taxes and fees

  • Verified guest reviews

    Over 20,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    370 of Cheltenham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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

Destinations to explore