Vacation rentals with outdoor seating in Winchcombe

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Top-rated outdoor seating rentals in Winchcombe

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Guest favorite

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

Sep 26 – Oct 3

G$20,867 GYD per night

Guest favorite

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.

Aug 22 – 29

G$22,781 GYD per night

Guest favorite

Loft in Temple Guiting

4.97 out of 5 average rating, 259 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

Jun 14 – 21

G$28,517 GYD per night

Guest favorite

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.

Oct 30 – Nov 6

G$32,906 GYD per night

Superhost

Cottage in Winchcombe

4.8 out of 5 average rating, 105 reviews

Idyllic cottage with direct Access to Cotswold Way

A rare opportunity to stay in a historic cottage. Nestled in an Area of Outstanding Natural Beauty, this 300-year-old and Grade II listed hideaway offers a peaceful, idyllic stay within a 15-minute drive from Cheltenham. It has a private garden with DIRECT ACCESS to the Cotswold Way! Great to cosy up on wet days, and even better to 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.

Aug 14 – 21

G$52,038 GYD per night

Guest favorite

Cottage in Stanley Pontlarge

4.99 out of 5 average rating, 159 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.

Dec 12 – 19

G$38,841 GYD per night

Guest favorite

Cottage in Bank Farm Barns

4.99 out of 5 average rating, 400 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

Feb 14 – 21

G$31,396 GYD per night

Guest favorite

Guest suite in Broadway

4.99 out of 5 average rating, 148 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.

Oct 3 – 10

G$25,355 GYD per night

Guest favorite

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

Jul 1 – 8

G$57,037 GYD per night

Guest favorite

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.

Oct 15 – 22

G$31,157 GYD per night

Guest favorite

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.

Jan 22 – 29

G$26,854 GYD per night

Guest favorite

Cottage in Winchcombe

4.92 out of 5 average rating, 424 reviews

Cotswold77 - Heart of the Cotswolds

Set in the heart of the Saxon village of Winchcombe a beautifully restored and luxuriously furnished Grade II listed cottage set over three floors with a pretty, sunny garden. Glorious countryside, Cotswold country pubs and a Michelin star restaurant all in walking distance. 6 miles from Cheltenham Racecourse and perfect for the Literature, Jazz and Science Festivals in Cheltenham. An Idyllic spot for exploring the Cotswolds!

Dec 2 – 9

G$66,150 GYD per night