Holiday rentals in Winchcombe

Guest suite in Winchcombe

4.91 out of 5 average rating, 195 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

4.93 out of 5 average rating, 144 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

4.84 out of 5 average rating, 192 reviews

Penny Cottage – Cozy 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.

4.93 out of 5 average rating, 127 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.

4.98 out of 5 average rating, 151 reviews

Little Nook Cottage - Dog Friendly & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

4.95 out of 5 average rating, 103 reviews

Cosy Cotswold Cottage in the centre of Winchcombe

Vineyard street is an unrivaled position in Winchcombe, a unique town in all it has to offer, where visitors are welcomed and quickly feel like locals and get to enjoy a real part of Cotswolds Life. No. 5 is a traditional cosy cottage, decorated and furnished to a high standard to ensure our guests comfort and needs. We are local owners and are on hand with any questions and to offer recommendations to make the most of your visit. Secure garden, dogs are very welcome, also allowed in pubs

Superhost

4.88 out of 5 average rating, 225 reviews

The Bolt Hole: King Bed, Log Burner, Dog Friendly

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

Guest house in Winchcombe

4.95 out of 5 average rating, 338 reviews

Charming ‘mini cottage’ bedroom and shower room

A pretty and private little Cotswold stone bakehouse converted to a bedroom and shower room with beautiful Cotswold views set in rolling farmland on edge of historic hamlet of Hailes. We are right on the Cotswold Way and an ideal stop off after the first leg or walk the myriad of footpaths around us straight from the door. Within easy access of Cheltenham racecourse and the lovely villages of the Cotswolds, the many country pubs or a visit to the amazing Giffords Circus.

Superhost

4.83 out of 5 average rating, 135 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.

4.92 out of 5 average rating, 509 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!

5 out of 5 average rating, 128 reviews

Home in Winchcombe

'Fifteen off the Green'- 1 Bedroom Cotswolds Home

Nestled on a close next to a peaceful tree-strewn lawn lies ‘Fifteen off the Green’. This fun and unique one bedroom home offers its guests the perfect balance of luxury and design whilst adding all creature comforts to make you feel right at home. Newly refurbished and designed with couples in mind, this home has everything you could need to cook up a storm or just to relax and unwind after a busy day exploring the Cotswolds.

4.96 out of 5 average rating, 248 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 for the winter. 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.

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Other great holiday rentals in Winchcombe

4.96 out of 5 average rating, 49 reviews

Character cottage with parking & enclosed garden

JuliaRating, 5 stars2 weeks ago

Teasel Cottage was an absolutely wonderful home base for our trip to the Cotswolds! In addition to the perfect location and furnishings of the home, Tishy provided plenty of helpful information to enhance our stay. Everything felt so cozy and matched the quintessential cottage feel we were looking for. The garden in the back was lovely as well. Highly recommend!

4.94 out of 5 average rating, 35 reviews

Cosy 2 Bedroom Cotswold Cottage with Large Garden

NeilRating, 5 stars2 months ago

A lovely place to stay in a beautiful location. Winchcombe is such a lovely village in a stunning part of the world and the cottage is a wonderful base to explore it. Cosy, well equipped with everything you need and with a very helpful, friendly and responsive host.Lovely.

4.86 out of 5 average rating, 29 reviews

Cosy Cotswold Cottage; Woodburner, Office, Parking

ThomasRating, 5 stars1 month ago

My partner, our 10 week old son and I had a great weekend stay here. The cottage is lovely - very clean and cosy and had everything we needed. Winchcombe is a nice town, the white heart serves very nice food and there are lots of nice country walks to do

Superhost

Flat in Winchcombe

4.63 out of 5 average rating, 75 reviews

Dawn Run, Studio Appartment.

KylieRating, 5 stars1 month ago

Pleasant stay at Helen's place, it had everything we needed. Lot's of very scenic walks to explore locally. Some really lovely restaurants e.g Winchcombe Indian Restaurant and The pheasant at Toddington.

4.94 out of 5 average rating, 80 reviews

Apartment in Winchcombe

The flat over the pub!

KateRating, 5 stars2 days ago

A delightful spot on the edge of the Cotwolds overlooking the Severn Valley, with the steam train going past! The accommodation is charming, secluded and well equipped. A simple and delicious breakfast of yoghurt and granola is provided, with tea and coffee making facilities. Good food is on hand at the Royal Oak next door or in Winchcombe 5 minutes drive away - with plenty of delightful walks over Gretton Hill into Winchcombe - approximately 30 minutes. Lots of other lovely, longer walks with pubs placed strategically along the way. This is a wonderful get-away for those seeking relief from the rush and bustle.

5 out of 5 average rating, 4 reviews

Cosy Cottage in the Cotswolds; Woodburner+Sleeps 4

SimonRating, 5 stars2 weeks ago

Lovely cottage. Super clean and with everything you need for an enjoyable stay. All really well thought out. Good sized rooms and a nice garden too. All in a lovely, quiet location very near to all the shops and pubs etc. Ideal for walkers or families looking to relax. Rebecca was an excellent host and super responsive. Highly recommend. We would happily stay here again.

Guest house in Cleeve Hill

5 out of 5 average rating, 75 reviews

Chapel End

NancyRating, 5 stars2 days ago

I've stayed in a lot of Airbnbs but this one really stands out. This is an incredibly spacious and beautiful property that looks even better than the photos – everything felt so nice and luxurious, from the kitchen with lovely gadgets and crockery to the bed sheets, the soaps provided, and even croissants left thoughtfully for us. It was perfect for me, my partner, our baby and dog – the enclosed courtyard was fab for us and the conservatory was great for enjoying the heavy rain that passed over us. Cleeve Hill is 30 seconds up the road and a stunning walk. There's food over the road at the pub (Greene King) and a massive Sainsburys about 12 mins drive. All in all, perfect. Hugely recommended!!