Vacation rentals with outdoor seating 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, 287 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.

4.96 out of 5 average rating, 159 reviews

Regency Apartment | Free Parking | Walk to Town

Ideally located within walking distance of Cheltenham town centre and the racecourse, this recently refurbished apartment offers a comfortable private living space within a large Regency house. Perfect for couples, the apartment sleeps 2, with space for up to 4 using additional single beds if required. Please contact us before booking if you would like the single beds prepared. I co-host with my son Patrick, husband John and daughter Rachel, and we’re always happy to help during your stay.

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.

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

The entrance of a historical building showcases a bright yellow door flanked by decorative wrought iron balconies. Potted plants are positioned on either side of the entrance, complementing the stone facade. Steps lead to the front door, framed by classic wrought iron fencing.

4.95 out of 5 average rating, 161 reviews

Regency flat, private courtyard, free parking

A beautiful recently renovated Regency flat in a grade II* building. We are 5 minutes walk to the city centre and 25 minutes to the Racecourse. The flat has its own front door and private courtyard. Virgin VIP package and high speed broadband plus Sky & BT Sports. One kingsize bed with soft linen sheets, plus one sofa bed for additional guests (book for 3 if you want the sofa bed). Well equipped kitchen. Separate shower room (off living room). Free parking nearby. Nest heating.

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.

4.96 out of 5 average rating, 146 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.

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, 239 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.

4.98 out of 5 average rating, 228 reviews

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 Cheltenham

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.

Vacation home in Cheltenham

The spacious open-plan living area features a comfortable gray sectional sofa with decorative pillows and a textured throw. A minimalist coffee table sits in front, accompanied by a stylish armchair. The modern kitchen is visible in the background, showcasing a clean and functional design.

4.94 out of 5 average rating, 220 reviews

* SUPERB CENTRAL CHELTENHAM ABODE *

Stylish and central redbrick house with 2 double bedrooms (both with king beds) one with en-suite, second shower room, large open plan kitchen/living/dinning room and permit parking. Easy walking distance to all that Cheltenham has to offer such as boutique shops, coffee shops, bars and restaurants. Perfect base for corporate clients and guests wishing to explore Cheltenham and the Cotswolds.

4.8 out of 5 average rating, 297 reviews

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 Cheltenham

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.

4.97 out of 5 average rating, 100 reviews

The lounge area features two comfortable sofas, one adorned with bright orange cushions. A small coffee table holds a collection of magazines. A decorative fireplace serves as a focal point, and a muted art piece hangs above it, contributing to a cozy ambiance.

Apartment in Cheltenham

Luxury Refurbished 2 Bedroom Regency Apartment

Superbly Appointed Regency Apartment Situated Along A Tree Lined Road Close To Cheltenham Centre Where You Will Find A Plethora Of Amazing Shops & Restaurants. With Its Own Private Entrance This Luxury Apartment Has Been Refurbished To A High Standard Throughout & Offers Spacious & Comfortable Living. It Is Suitable For Up To 4 Guests, Couples, Families Or Corporate Stays.

5 out of 5 average rating, 298 reviews

A stone cottage is positioned among trees and greenery, featuring a well-maintained exterior. Sunlight filters through the branches, highlighting the natural surroundings. A gravel path leads to the entrance, creating an inviting transition from the landscape to the home.

Cottage in Withington

Boutique 1 bedroom Cotswold Cottage

Kick back and relax in this beautiful location. A stylish stone cottage in the heart of the Coln Valley, arguably the prettiest part of the Cotswolds. The cottage is set within the 16 acres of land belonging to the main house. The perfect place for scenic walks and romantic nights in. A peaceful retreat, just 20 minutes drive from both Cirencester and Cheltenham.

4.99 out of 5 average rating, 145 reviews

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 Southam

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A spacious dining area features a long wooden table surrounded by benches, complemented by potted plants. Bright lighting enhances the modern decor, which includes a decorative wall display and a mirror. An open kitchen area with bar stools is visible in the background.

4.99 out of 5 average rating, 125 reviews

Stunning house sleeps 14, parking, walk to town.

An elegant dining room features a round wooden table surrounded by six intricately designed chairs with a wrought iron finish. Richly colored walls are complemented by patterned drapes and a decorative chandelier, creating a distinctive and inviting atmosphere.

4.93 out of 5 average rating, 209 reviews

Cotswolds - Cheltenham, whole house large garden

5 out of 5 average rating, 274 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

4.94 out of 5 average rating, 154 reviews

Home in Painswick

Peaceful Cotswolds Chapel Breathtaking Valley View

4.97 out of 5 average rating, 156 reviews

The open-plan kitchen and living area features a light wooden floor and a contemporary design. A spacious kitchen island is complemented by a dining table, while a comfortable seating area includes a two-seater sofa adorned with an orange cushion. Large windows allow natural light to fill the space.

Home in Cirencester

*NEW* Wardall's Cottage - Central Location!

A stone building is shown with a private entrance featuring a white gate. A small window is visible at the top, illuminating the structure. The roof is lined with antennas, and a cloud-filled sky provides a soft backdrop.

4.99 out of 5 average rating, 177 reviews

Detached Cotswold Stone Coach House

4.91 out of 5 average rating, 165 reviews

Luxury Detached Home with AC and Gated Parking

4.98 out of 5 average rating, 405 reviews

A modern barn exterior features a slate roof and large glass doors that open to a patio area, surrounded by well-maintained greenery. Potted plants and chairs are positioned outside, inviting relaxation in the scenic, tranquil setting.

Home in Sherborne

A Perfect Cotswold Getaway in Peaceful location

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 121 reviews

A private garden space features lush green grass bordered by roses and plants. A wooden gate labeled 'Secret Garden' opens to a cozy dining area with a table and four chairs, set against a backdrop of trees and a stylish shed.

Apartment in Broadway

Cotswolds Place - stylish design in ❤️ of Broadway

4.93 out of 5 average rating, 198 reviews

A spacious living room is highlighted by deep green walls paired with a high ceiling. Two comfortable leather sofas surround a wooden coffee table, while soft light is provided by elegant chandeliers. The kitchen area features cream cabinetry and art pieces adorn the walls, adding character.

Apartment in Gloucester

Grand regency apartment with park views nr Docks

Apartment in Weston-sub-Edge

A bright kitchen area is complemented by a dining table with two chairs, positioned beside a shelving unit filled with books. The kitchen features modern appliances, and a spacious layout leads to a cozy double bedroom visible in the background, framed by soft natural light.

4.97 out of 5 average rating, 760 reviews

The Quart

4.91 out of 5 average rating, 243 reviews

A cozy sitting room features a wooden beam ceiling and a central open fire. A comfortable sofa and armchairs are decorated with colorful cushions. A rustic wooden coffee table is placed in front of the seating area, and artwork adorns the walls, enhancing the room's inviting ambiance.

Apartment in Broadway

The Old Post Office, Central Broadway with Garden

Apartment in Great Malvern

The Victorian house is nestled within a mature garden, featuring a light-colored exterior and elegant sash windows. A pathway leads to the entrance, which is framed by greenery and flower beds, inviting guests into a serene outdoor space.

4.96 out of 5 average rating, 524 reviews

Garden Flat right on Malvern Hills

4.95 out of 5 average rating, 192 reviews

A small balcony table is set with two glasses of orange juice and a plate of croissants, accompanied by two patterned chairs. The view displays a peaceful landscape with grazing horses beyond the railing, framed by trees under a clear blue sky.

Apartment in Saintbury

A Beautiful luxury two bedroom Hayloft

4.99 out of 5 average rating, 123 reviews

A modern lounge area features a comfortable blue sofa adorned with decorative cushions. Soft lighting is provided by a standing lamp beside the sofa, and a small side table complements the space. Large double doors open to a private walled garden, enhancing the room's brightness.

Apartment in Tetbury

The Hideaway - With Large Courtyard Garden

4.92 out of 5 average rating, 705 reviews

A tranquil outdoor area features raised garden beds with plants, bordered by gravel pathways. A cozy seating arrangement is visible near the entrance of a rounded structure, which includes large windows. Surrounding greenery adds to the peaceful countryside setting.

Apartment in Horsley

Gatewillow Garden Room

Condo rentals with outdoor seating

4.97 out of 5 average rating, 323 reviews

The historic stone exterior features a castle-like design with arched windows and a decorative entrance. A landscaped garden surrounds the building, showcasing vibrant flowers and a small pond. A stone path leads to a wooden bridge, enhancing the tranquil outdoor setting.

Condo in Stroud

Private apartment in stunning historic house

4.98 out of 5 average rating, 147 reviews

A charming stone annex is set amidst a lush garden, featuring well-manicured grass and low shrubs. A small, outdoor seating area with green furniture invites relaxation, while the warm stone facade is complemented by several windows allowing natural light. The peaceful surroundings enhance the tranquil setting.

Condo in Ashton Keynes

The Annex

Condo in Bourton-on-the-Water

A bright studio space features a king-sized bed adorned with a vibrant orange throw and decorative pillows. Alongside, a cozy sofa and a rattan chair provide comfortable seating. Natural light filters through the angled ceiling, enhancing the airy feel of the room.

4.97 out of 5 average rating, 342 reviews

Stylish studio apartment in Bourton on the Water

4.98 out of 5 average rating, 175 reviews

A dining table is set for two on a sun terrace, featuring dishes, glasses, and decorative flowers. A warm sunset casts a golden glow over the scene, enhancing the peaceful ambiance. Scenic views of the surrounding nature are visible in the background.

Condo in West Malvern

Malvern hillside apartment with spectacular views.

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.

4.88 out of 5 average rating, 135 reviews

Town Centre Penthouse with Hot Tub 22

4.98 out of 5 average rating, 104 reviews

A spacious studio layout features a comfortable double bed next to a cozy sectional sofa. Soft lighting from a table lamp and large window brightens the room, while a kitchenette with modern amenities is visible in the background. A striped rug adds texture to the wooden floor.

Condo in Shurdington

Modern Studio Apt close to village pub & bus stop

4.95 out of 5 average rating, 114 reviews

A stone annex is depicted beside a gravel path leading up a steep, grassy slope. A large tree provides shade, while the clear blue sky adds brightness to the scene. The entrance door is prominently featured, framed by natural stone walls.

Condo in Southam

Self-contained annex on Cleeve Hill Common.

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.