Holiday rentals with outdoor seating in Winchcombe

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Top-rated rentals with outdoor seating in Winchcombe

Guests agree: these rentals 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, 122 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

9–16 Oct

£80 per night

Guest favourite

Shepherd’s hut in Winchcombe

4.96 out of 5 average rating, 440 reviews

Idyllic, Cotswold Views, En suite, TV/Wi-Fi

Scandinavian styled, ensuite, luxury Shepherd's Hut set in peaceful private countryside. Bright & open aspect with extensive hillside views. Perfectly located in an Area of Outstanding Natural Beauty, The Cotswolds. Local & National Walking Trails on the doorstep. Picturesque 20/25 minute walk or cycle (hire one of our e-bikes!) to medieval Winchcombe; home to the fascinating & majestic Sudeley Castle. You’ll also find many unique, independent shops, excellent restaurants, superb cafés & pubs.

5–12 Jun

£84 per night

Guest favourite

Home in Woodmancote

4.98 out of 5 average rating, 126 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.

10–17 Dec

£127 per night

Guest favourite

Loft in Temple Guiting

4.97 out of 5 average rating, 260 reviews

Hectors Loft Spacious Cotswold Hideaway

Wonderful peaceful space for 2. Your own drive and entrance to off road parking adjacent to the Loft, Outside patio and garden. Great local pubs and walk to cafe in the near by village of Guiting Power. Airy, bright living space with separate bedroom and bathroom. Country walks, quiet pub lunches, discover many interesting places - Bourton on the Water, Broadway, Chipping Campden, Stow on the Wold, Stratford upon Avon, Moreton in Marsh. All within 30 minutes travelling by car. 300mb wifi

28 Jun – 5 Jul

£115 per night

Guest favourite

Cottage in Stanley Pontlarge

4.99 out of 5 average rating, 160 reviews

Stunning Cotswold cottage, log burner, Winchcombe

Gorgeous romantic Cotswold cottage with direct access to walks. Up to 2 well behaved dogs welcome. The Old Mill House is a luxury retreat in Stanley Pontlarge, 2 miles to Winchcombe, 5 miles Cheltenham Racecourse, 9 miles central Cheltenham. Living room with TV and logburner, bedroom with kingsize bed, kitchen with microwave, dishwasher, induction hob, oven Nespresso machine, Smeg fridge/freezer. Shower room. Neal's Yard toiletries. Fast broadband. EV charging. Muddy paw pet washer.

25 Feb – 4 Mar

£149 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.

23–30 Oct

£116 per night

Guest favourite

Cottage in Bank Farm Barns

4.99 out of 5 average rating, 404 reviews

Idyllic Dog Friendly Barn , Summerhouse / Paddock

“Hare Barn” is self contained original barn conversion We offer guests on B & B basis the perfect place to relax and unwind. Many character features including romantic bedroom, private patio and access to my paddock offering spectacular views towards Bredon Hill and countryside. Use of The Stables Summerhouse with sheltered seating., BBQ, Firepit & Fridge. Extensive network of footpaths perfect for dog lovers and ramblers, leading direct from barn. Up to 3 dogs stay free

10–17 Jan

£114 per night

Guest favourite

Guest suite in Broadway

4.99 out of 5 average rating, 150 reviews

Cosy countryside studio with log burner stove

The Studio at Hoo Lodge provides cosy accommodation for two in the tranquil village of Laverton, near Broadway Double French doors to front Exposed beam ceiling & stone end wall Log burner, SMART TV & leather sofa Iron double bed & king-size duvet Kitchen diner area, gas cooker, fridge, kettle & toaster Shower room with dual shower head Linens, towels & logs included. Patio with teak table & chairs Ideal location for exploring, walking, running & biking or just relaxing.

11–18 Feb

£98 per night

Guest favourite

Cottage in Winchcombe

4.92 out of 5 average rating, 228 reviews

No. 15 North Street, Cotswolds cottage

Rustic 200 year old Cotswolds cottage, lovingly restored into the ultimate countryside retreat- pet friendly, huge inglenook fireplace, roll top bath, private courtyard garden and a stones throw from the local pub... No.15 is perfectly positioned in the heart of Winchcombe, surrounded by independent shops and award winning pubs and restaurants. Just a short stroll from Sudeley Castle and the Cotswolds Way, this cosy cottage is the perfect place to escape the every day

1–8 Jul

£219 per night

Guest favourite

Cottage in Winchcombe

4.84 out of 5 average rating, 105 reviews

Barley Cottage

A character filled centrally-located cottage sure to enable a relaxing stay in our picturesque Cotswold town. An indoor log burner keeps the place cosy, and a small patio with garden to the rear of the cottage allows for outdoor dining during the summer. Cook for yourselves in the fully equipped kitchen or eat out at the many eateries in town right on the doorstep. A fully refurbished bathroom with walk in shower and sofa bed that can sleep 2 are also at your leisure.

10–17 Sept

£123 per night

Superhost

Cottage in Winchcombe

4.8 out of 5 average rating, 107 reviews

Idyllic cottage with direct Access to Cotswold Way

17th-century gem: original features, tranquil stream, and a private picturesque garden with DIRECT ACCESS to the Cotswold Way! Stay in a historic cottage. Nestled in an AONB, this Grade II listed hideaway offers a peaceful, idyllic stay within a 15-minute drive from Cheltenham. Great to cosy up on wet days, explore the area, or enjoy our garden on a sunny day. Perfect for romantic getaways, nature lovers or people who want to escape the humdrum of everyday life.

23–30 Jun

£175 per night

Guest favourite

Guest house 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.

25 Nov – 2 Dec

£105 per night