Holiday houses in Winchcombe

Guest suite in Winchcombe

4.91 out of 5 average rating, 198 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, 146 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, 193 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, 128 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, 153 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!

4.91 out of 5 average rating, 120 reviews

Beam House, Winchcombe, sleeps 6 + 2

We don't just offer you somewhere to sleep; at Beam House you can indulge in all the Cotswolds and Cheltenham have to offer knowing you can return to a uniquely styled period house in Winchombe's historic Gloucester Street. Expect soft cotton linens, a wood burning stove, Farrow and Ball paint, exposed beams and stone and oak floors. We offer a unique and stylish retreat ideal for relaxing and exploring. We can host 6 (1 king, 2 double) plus 2 (a sofa bed is available in the drawing room).

4.94 out of 5 average rating, 105 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

4.88 out of 5 average rating, 227 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.

4.95 out of 5 average rating, 339 reviews

Guesthouse in Winchcombe

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.

4.83 out of 5 average rating, 136 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, 511 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, 129 reviews

'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.

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Other great holiday rentals in Winchcombe

4.92 out of 5 average rating, 26 reviews

Period 2 bed cottage with garden and amazing views

SallyRating, 5 stars1 week ago

Amanda's cottage is beautiful. The most outstanding feature is the garden. The table and chairs at the end of the garden looked out over green fields and felt so private and peaceful. The whole area was lovely with countryside walks really near to the cottage and pubs within n walking distance.

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

4.8 out of 5 average rating, 82 reviews

Castle in Winchcombe

Castle Gatehouse, Tower at Sudeley Castle

EmilyRating, 5 stars1 week ago

Wonderful place in a great location. walkable to all restaurants and the towns core. walkable up to the castle. Everything was clean, nicely decorated and fairly new. the heating was a little hard to figure out. Not necessary but would be nice to have a TV in the rooms. The patio was lovely to sit and watch all the dogs walking the trails. highly recommend!!

4.94 out of 5 average rating, 80 reviews

Condo in Winchcombe

The flat over the pub!

KateRating, 5 stars2 weeks 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, 7 reviews

Cosy Cottage in the Cotswolds; Woodburner+Sleeps 4

EllisRating, 5 stars3 days ago

Lovely cottage to stay in, would happily stay here again.

4.99 out of 5 average rating, 79 reviews

Cottage on the Cotswold Way

SusannahRating, 5 stars5 days ago

We had a great stay here in Winchcombe! The cottage is lovely—and the perfect base for exploring the Cotswolds. Winchcombe is a charming town, very walkable, with lots of restaurants and shops and very pretty buildings and gardens. The cottage was comfortable and well equipped. We loved the convenience of having two bathrooms, all of the cooking supplies, and the washer. We also appreciated the welcome snacks and breakfast foods. Simon was an excellent host—very friendly and flexible. I’d highly recommend staying here! One caution would be that the stairs to the top floor are a little tricky, so anyone staying up there needs to be aware of that.

4.93 out of 5 average rating, 91 reviews

Place to stay in Stanton

The Loft/Annex at New House Farm

MarieRating, 5 stars3 weeks ago

Really good location if you want to walk the Cotswold Way and/or go to Broadway. We walked to Broadway which took a couple of hours, and then got a bus back as there is a bus that leaves Broadway at 5.39pm and drops you 5 mins from property location which was ideal.