Cottage vacation rentals in Winchcombe

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Top-rated cottage rentals in Winchcombe

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Guest favorite

Cottage in Cheltenham

4.91 out of 5 average rating, 448 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.

Guest favorite

Cottage in Winchcombe

4.94 out of 5 average rating, 101 reviews

Thimble Cottage. Winchcombe

Charming 200 year old Cotswold stone Cottage with oak beams and log burner. Situated in the heart of the ancient Saxon town of Winchcombe. Two lovely bedrooms, one with king size bed and the second with two single beds. Fully furnished to a high standard with an attractive long garden and patio seating area. Close to all amenities, pubs, restaurants and local produce shops i.e bakers, butchers and delicatessen. Sudeley Castle and grounds are a short walk from the cottage. Pet friendly No smoking

Guest favorite

Cottage in Winchcombe

4.83 out of 5 average rating, 183 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.

Guest favorite

Cottage in Alstone

4.95 out of 5 average rating, 110 reviews

Country cottage in a Cotswold village

Woodpecker Cottage is a 1 bed barn style cottage in the grounds of a 17th Century farmhouse with countryside views. Within easy reach of Broadway, Winchcombe, Stow-on-the-Wold, Chipping Campden & Cheltenham, it is an ideal base for those wanting to explore the Cotswold towns & villages. Ideally located for Cheltenham Racecourse, Sudeley Castle & the Bugatti Prescott Hill Climb. For keen walkers it’s on the Winchcombe Way with plenty of other local footpaths, Cleave Hill & Bredon Hill nearby.

Guest favorite

Cottage in Winchcombe

4.93 out of 5 average rating, 114 reviews

The Feathered Nest an idyllic Cotswolds escape.

The Feathered Nest is a delightful Cotswolds escape at any time of year. Vineyard Street is a picture postcard street in the heart of the Anglo-Saxon town of Winchcombe in the North Cotswolds. Paul and Amanda have lovingly restored this former wool cottage into a boutique two bedroom cottage with all the modern fixtures and fittings required by our discerning guests. The property has a stunning private courtyard garden which is a perfect retreat to listen to the bells of St Peter's at sundown.

Guest favorite

Cottage in Bank Farm Barns

4.99 out of 5 average rating, 464 reviews

Stunning Dog Friendly Barn , Summerhouse / Paddock

“Hare Barn” is self contained original barn conversion dating back to 1860. 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 our 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

Superhost

Cottage in Winchcombe

4.88 out of 5 average rating, 208 reviews

Chic Cottage, King Bed, Log Burner, Dog Friendly

The Bolt Hole is a beautiful, refurbished, dog-friendly 🐶 Cotswold stone cottage with King bed - Late check-out 11 am + NO cleaning or Airbnb fees - Log burner and New Kitchen w/ dishwasher + Washing Machine - Super Comfortable UK King-Size bed - Fantastic walks from the doorstep - En-suite bathroom with large shower 🚿+ roll-top bath 🛀 - Smart TV - Cot and highchair 👶 Nestled in the heart of stunning Winchcombe; steps away from delightful restaurants, cafes, and historic Sudeley Castle.

Guest favorite

Cottage in Stanley Pontlarge

4.99 out of 5 average rating, 202 reviews

Stunning Cotswold cottage, log burner, Winchcombe

Gorgeous romantic Cotswold cottage with direct access to walks. One well behaved dog is welcome or enquire. 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.

Superhost

Cottage in Winchcombe

4.85 out of 5 average rating, 485 reviews

Apple Tree Cottage, 2 bedroom (double & king beds)

Apple Tree Cottage is a charming Cotswold stone cottage, located right in the heart of Winchcombe with country pubs and shops just a stone's throw from the front door. Located on the most photographed street in the ancient Anglo-Saxon town of Winchcombe. We provide complimentary welcome pack including my homemade plum jam plus our family's delicious Organic Gin+tonic! The cottage living room ceiling is quite low (as is traditional) so taller guests may wish to factor this into their stay

Guest favorite

Cottage in Broadway

5 out of 5 average rating, 122 reviews

Hobleys Cottage Stanton Nr Broadway

Hobleys Cottage is positioned on the edge of the historic village of Stanton which is widely regarded as one of the most picturesque in the Cotswolds. Recently refurbished the luxury accommodation is light and spacious with a well-equipped kitchen, open plan dining and sitting room. Wake up to stunning views over the adjoining pasture fields; a relaxing setting and a perfect base from which to explore the Cotswalds. The village pub The Mount Inn is within walking distance.

Superhost

Cottage in Winchcombe

4.83 out of 5 average rating, 118 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.

Superhost

Cottage in Winchcombe

4.84 out of 5 average rating, 128 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.