Cottage vacation rentals in Winchcombe

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Top-rated cottage rentals in Winchcombe

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Guest favorite

Cottage in Cheltenham

4.9 out of 5 average rating, 417 reviews

The Bothy cottage in the Cotswolds

The Bothy is a conversion of a 17th Century Cotswold stone stable and a 20th Century kennel building. On the ground floor is the living room with a beautiful wood burning stove, a fully equipped kitchen, a comfortable double bedroom and a modern shower room. Whilst upstairs, which is accessed from a narrow oak staircase, you can find the twin bedroom. The living room has been fitted to retain all its original features and is furnished in period style. I have included many Georgian and Victorian pieces and have also included a large settee and two arm chairs, dining table and chairs for 4, corner cupboard and a dash of the 21st Century with a Sky television. The Bothy is beautifully situated in the Postlip Coombe on the leeward side of the Cotswolds highest hill and yet only minutes from Winchcombe, a classic Cotswold "wool" town, renowned for its excellent shops, restaurants and architecture.

Feb 28 – Mar 7

R2,377 ZAR per night

Guest favorite

Cottage in Winchcombe

4.84 out of 5 average rating, 159 reviews

Penny Cottage - Cosy Cotswold cottage

Penny Cottage is in the heart of the former Saxon town of Winchcombe. It is a traditional Cotswold cottage with a working inglenook fireplace. It is on the Cotswold Way and has access to miles of country walks. Sudeley Castle, the resting place of the only Queen of England to be buried outside a royal palace, is within walking distance. A variety of pubs and restaurants can all be found within a 5 minute walk. The town also boasts a variety of independent shops, and two small supermarkets.

Apr 2 – 9

R2,421 ZAR per night

Guest favorite

Cottage in Badsey

4.98 out of 5 average rating, 233 reviews

Letterbox Cottage in Badsey

Quietly tucked away down the end of Old Post Office Lane. Letterbox Cottage can be found down a private gravel drive. Recently renovated but still has the charm of a old cottage, with an opened planned living space, this 2 bedroom cottage is perfectly located within easy reach of some of the Cotswold's prettiest villages and towns. Within easy reach of both Broadway and Chipping Campden and only 30 minutes from Stratford Upon Avon. Home from home experience awaits. A well behaved dog is welcome

Nov 18 – 25

R2,192 ZAR per night

Guest favorite

Cottage in Ashton under Hill

4.88 out of 5 average rating, 171 reviews

Character thatch cottage in a fantastic location.

Located at the foot of Bredon Hill with easy access to Cheltenham, Stratford upon Avon and the Cotswolds. No.1 The Cottages is a 16th Century Thatch beautifully restored and furnished in its owners unique, quirky and comfy style. The galley kitchen is fully equipped, the flagstoned lounge is complete with a log burner and the main bedroom has a kings size bed and feather everything!. The second bedroom is perfect for a little one and there's even a mini library full of books, games and DVDs.

Oct 18 – 25

R2,195 ZAR per night

Guest favorite

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.

Feb 17 – 24

R3,516 ZAR per night

Guest favorite

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

Jan 10 – 17

R2,682 ZAR per night

Guest favorite

Cottage in Winchcombe

4.89 out of 5 average rating, 188 reviews

Luxurious Escape: Charming Dog-Friendly Cottage

Welcome to The Bolt Hole, a unique, Cotswold stone cottage, in the centre of stunning, Winchcombe close to restaurants, cafes and historic Sudeley Castle. - Romantic bedroom & super comfortable Hypnos king-size mattress - 400+ thread-count cotton bed linen - En-suite bathroom: large shower and roll-top bath - Wall-mounted Smart TV - Dog friendly - Romantic log burner - Large refurbished kitchen - Cot available Complimentary late check out of 11am and no cleaning fees

Nov 6 – 13

R5,275 ZAR 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

R5,073 ZAR 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 12 – 19

R2,828 ZAR 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.

Jun 23 – 30

R4,028 ZAR per night

Guest favorite

Cottage in Winchcombe

4.92 out of 5 average rating, 425 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

R6,004 ZAR per night

Guest favorite

Cottage in Winchcombe

4.97 out of 5 average rating, 222 reviews

No61 - Cosy Cotswold Cottage in Winchcombe

No61 sleeps 3 adults plus an infant in a cot and is situated on a quaint residential road just outside the Cotswold town of Winchcombe. The cottage has private parking, two comfy bedrooms and a wood burning stove. The flower filled garden has a suntrap decking area for the summer with table and chairs. No61 is a 5 minute walk from a selection of restaurants, pubs and coffee shops.

Nov 19 – 26

R2,452 ZAR per night