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, 278 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
A spacious bedroom is presented with a large bed adorned with soft bedding, accented by two bedside lamps. A cozy chair is positioned nearby, and a patterned rug spans the floor, adding warmth. Fresh towels are neatly arranged for convenience.
Condo in Henleaze
5 out of 5 average rating, 113 reviews

Luxury spacious Apartment central Cheltenham

Festival Lodge is now a firm favourite spacious luxury basement apartment in a beautiful large Grade II listed Regency Home. Situated in a brilliant location in central Cheltenham (Montpellier), less than 2 minutes walk from restaurants, wine bars, boutique shops, parks and Cheltenham Festival events. Also walkable to the Cheltenham Race course and station. Our luxury welcome pack includes wine, complimentary tea, coffee, milk, eggs and bread, breakfast cereal and jam. Secure offroad parking.

Top Guest favourite
The living area features a cozy seating arrangement with a neutral-toned sofa and decorative cushions. A natural woven pendant light hangs above, illuminating the space. A rustic coffee table sits on textured flooring, accompanied by warm tones and a charming wreath adorning the entrance.
Cottage in Winchcombe
4.98 out of 5 average rating, 203 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
4.94 out of 5 average rating, 166 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, 180 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, 260 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
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, 138 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.

Top 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
4.92 out of 5 average rating, 233 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
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, 157 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.

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, 611 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, 282 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.

Top Guest favourite
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.
Guesthouse in Cleeve Hill
4.99 out of 5 average rating, 127 reviews

Chapel End

Set on Cleeve Hill, this converted chapel is a unique and peaceful getaway. Located on the Cotswold Way, it is ideal for walkers, is dog friendly and has fabulous views. Next door is the Rising Sun pub and it is a short walk to Cleeve Hill Golf Club. It is also perfect for horse-racing enthusiasts with the Cheltenham Racecourse close by.

Popular amenities for Cheltenham outdoor seating rentals

When is the best time to visit Cheltenham?

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Avg. price$266 NZD$273 NZD$403 NZD$287 NZD$301 NZD$308 NZD$308 NZD$316 NZD$302 NZD$277 NZD$287 NZD$299 NZD
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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 $69 NZD 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