Vacation rentals with outdoor seating in Tewkesbury Borough

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Top-rated accommodations with outdoor seating in Tewkesbury Borough

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Guest suite in Winchcombe

4.93 out of 5 average rating, 121 reviews

The Annex Self contained suite on a working farm

A self-contained annex on a working farm in the beautiful Cotswold town of Winchcombe. Sitting above the medieval town, the room has spectacular views of the surrounding cotswold hills. Situated 10 minutes walk from the centre of town with lots of pubs, shops and restaurants. Right on the Winchcombe Way and close to the Cotswold Way its ideal for walkers. Secure cycle storage is also available. Broadway, Stow-on-the Wold, Bourton-on-the -Water Cheltenham, Stratford and Oxford are all drivable

Oct. 5 – 12

$138 CAD per night

Guest favourite

Shepherd’s hut in Winchcombe

4.97 out of 5 average rating, 127 reviews

Stunning Cotswold Views, Idyllic, En suite TV/WiFi

Scandinavian styled, ensuite, luxury Shepherd's Hut set in idyllic private countryside. Extensive hillside views. Perfectly located in an Area of Outstanding Natural Beauty (AONB) in The Cotswolds. National Walking Trails on the doorstep. Picturesque walk or e-bike to medieval Winchcombe; home to the fascinating & majestic Sudeley Castle, many interesting shops, excellent restaurants, superb cafés & pubs. Just one other beautiful Shepherd’s Hut is also available & both can be booked together.

Aug. 31 – Sep. 7

$162 CAD per night

Guest favourite

Home in Boddington

4.98 out of 5 average rating, 100 reviews

Stunning Victorian Mill, 3 BDR

Oriri presents Boddington Mill, a stunning countryside retreat steeped in history and rural charm. Multiple levels intersect the original mill parts for a generous and sociable living space. A south-facing garden includes alfresco dining, wood-fired hot tub, and large lawn, home to fruit-bearing trees and wildlife. Bedrooms feature luxury bedding; vaulted, oak-beamed ceilings; and period windows. Guests will enjoy fine comforts, modern media, and a kitchen fit for the highest culinary ambitions.

Jan. 30 – Feb. 6

$901 CAD per night

Guest favourite

Barn in Bushley

4.95 out of 5 average rating, 193 reviews

Courtyard at Hither Ham House, Stunning retreat

Welcome to the Courtyard at Hither Ham House, a stunning little hideaway. Relax in the King size Bed and enjoy the peaceful setting on offer, it has a fully equipped Kitchen with Breakfast bar and the sofa bed can accommodate one extra person. Private entrance and parking on site don't forget to bring your rackets as free use of the Tennis Court is available. Highspeed internet is included and enjoy an alfresco drink outside. Easy access for Cotswolds, Cheltenham, Tewksbury and Upton upon Severn

Sep. 5 – 12

$119 CAD per night

Guest favourite

Home in Woodmancote

4.98 out of 5 average rating, 125 reviews

The Cotswold Holiday Home.

Innisfree was built in 1907 from local Cotswold stone, recently extended and renovated to a high standard with modern contemporary fittings making for a very warm and comfortable holiday home. Bedrooms have been fitted with new beds for flexible accommodation of singles and superking size doubles. A single child’s bed and travel cot may be added to the master suite. A double garage provides parking for two cars. The house has large enclosed gardens with outside furniture and BBQ fireplace.

Jun. 5 – 12

$218 CAD per night

Guest favourite

Guesthouse in Leigh

4.92 out of 5 average rating, 155 reviews

Cosy countryside retreat.

The Nest is a self contained detached annexe set in the peaceful Gloucestershire village of The Leigh. The property has been newly refurbished and is available for up to 2 people with access to a secluded garden space within our lovely orchard surroundings. The property has easy access and ample parking. Located within easy reach of Cheltenham, Tewkesbury, Gloucester, The Malverns, Cotswolds and M5, the accommodation is in a perfect position for exploring all that the area has to offer.

Oct. 8 – 15

$156 CAD per night

Guest favourite

Home in England

4.94 out of 5 average rating, 249 reviews

Cotswold Garden Accomodation near Racecourse/Univ

Home from home , self contained, modern airy accomodation close to Cheltenham. The park & ride bus is 500m from us provides easy travel into the town centre and direct to Cheltenham Railway Station, or leave your car in our parking space . A great base to explore the Cotswolds with all the bars and restaurants of the Regency town close by. Stretch your legs in the beautiful Pittville Park and Pump rooms about ten minutes stroll from, perfect base for cycling and walking in the Cotswolds.

Jul. 5 – 12

$144 CAD per night

Guest favourite

Home in Gloucestershire

4.98 out of 5 average rating, 109 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.

Dec. 3 – 10

$167 CAD per night

Guest favourite

Guesthouse in Withington

4.99 out of 5 average rating, 257 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.

Dec. 4 – 11

$180 CAD per night

Guest favourite

Condo in Gloucestershire

4.97 out of 5 average rating, 149 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.

Feb. 19 – 26

$147 CAD per night

Guest favourite

Apartment in Gloucestershire

4.97 out of 5 average rating, 170 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.

Jun. 5 – 12

$139 CAD per night

Guest favourite

Apartment in Gloucestershire

4.88 out of 5 average rating, 234 reviews

Luxury garden flat in the heart of Cheltenham

A beautifully decorated, centrally located garden apartment within a traditional Regency townhouse. Perfect for couples, small families or groups of friends to explore the Cotswolds or attend the various Cheltenham festivals. Private off-road parking, cosy furnishings and a 5 minute walk to Montpellier and the Promenade make the Garden Flat a convenient and comfortable stay

May 16 – 23

$182 CAD per night