
House vacation rentals in Winchcombe
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Quick stats about house rentals in Winchcombe

Total vacation rentals
Explore 50 vacation rentals in Winchcombe

Nightly prices starting at
Winchcombe vacation rentals start at G$21,037 GYD per night before taxes and fees

Verified guest reviews
Over 2,200 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Winchcombe vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winchcombe rentals

4.9 Average rating
Winchcombe stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Winchcombe
Guests agree: these houses are highly rated for location, cleanliness, and more.

Boddington Mill
Boddington Mill is a stunning countryside retreat in the heart of the Cotswolds, steeped in history and rural charm. The building retains industrial mill parts which intersect multiple levels for a unique and generous living space. Its south-facing garden includes outside dining, wood-fired hot tub, and large lawn, home to wildlife and fruit-bearing trees. Inside, the three king sized bedrooms feature luxury bedding beneath vaulted, oak-beamed ceilings and period windows. Sky TV, Sonos speakers.

Comfortable Cotswold house with fabulous views
Comfortable Cotswold house with beautiful views over wide countryside yet very close to the centre of Stow on the Wold. Downstairs there is a well equipped modern Kitchen, a Cloakroom and a Living room leading into a spacious new Orangery. Upstairs there are two bedrooms, one with a double bed and the other with a King size bed. There is a bathroom with bath and shower. Outside there is parking space for several cars and at the front of the house there is a terrace leading onto an open garden

Breathtaking Cotswolds Restored Chapel Valley View
Step into a rare and remarkable stay at ‘The Old Church’, a lovingly restored & renovated 1820s chapel nestled on the hillside in the idyllic Cotswolds village of Sheepscombe. This enchanting property blends timeless character & period charm with a relaxing contemporary feel. A truly unique picturesque countryside escape. Located in a tranquil woodland setting on the edge of Blackstable Nature Reserve with scenic valley walks, a rustic village setting, a playground & lovely pub down the lane.

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).

Luxury Cotswolds Cottage with Hot Tub
Escape to our luxurious Cotswolds holiday cottage with a hot tub! Located in the enchanting Cotswold region, our snug-luxe cottage offers the perfect break. With a landscaped garden and proximity to Cheltenham, it's ideal for race enthusiasts and explorers. Experience an unforgettable weekend getaway, family holiday, or celebration with friends in style and comfort. Book now to indulge in the beauty of the Cotswolds and enjoy relaxation, scenic trails, and the charm of Cotswolds living.

Premium 4-Bed Cotswolds Escape & Relaxing Retreat
Welcome to our 4 bedroom home located in the village of Woodmancote, near Cleeve Hill & Cheltenham, right next to The Cotswold Hills, Known as the walking capital of England and AONB. Beautifully presented throughout, this self-catering home benefits from an open plan fully equipped kitchen / lounge / diner with sliding patio doors leading out to the garden, separate snug with TV. 4 double bedrooms that can accommodate up to 8 guests, en suite to the Master and a modern family bathroom.

Cosy Cotswold Cottage near Cheltenham
Our 200 year old cottage provides the perfect getaway for walkers, cyclists, families or those just wanting some time to unwind and explore the beautiful Cotswold country side. Although the accommodation has been recently refurbished with a new kitchen and bathroom it still retains a wealth of original features including exposed oak beams, stone walls and wood floors. Pubs, cafes, restaurants, shops, Sudely Castle are within walking distance. Cheltenham race course is 6 miles away.

The Woodshed
We are located in the countryside but within easy reach of Cheltenham, Stratford-on-Avon, the Cotswolds, the Malverns and Worcester. We are a working farm at the foot of Bredon Hill, just over one mile from the local village which has a great pub. There are many great walks and cycle routes around and we also have a large pond which is great for fishing in or relaxing by. The Woodshed is great for couples, solo adventurers, business travellers, and families (with children).

4 Vineyard Street
A character filled Cotswold stone cottage including an indoor log burner and a patio with a garden to the rear of the cottage with a coal BBQ which allows for outdoor dining during the summer. Two double bedrooms allow plenty of space for families or friends to holiday in this stylish and welcoming home. This central location means all local amenities are just yards from your front door. See our Cotswold Escapes website and socials for more information and pictures

'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.

Cottage luxe in The Cotwolds
Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Kingfisher Cottage, Disabled Friendly, Cotswolds
Nestled in the wonderful market town of Winchcombe, this relaxing retreat in the heart of the Cotswolds is the perfect base for a family or group getaway to this beautiful part of the world. Experience sweeping countryside views and a tranquil garden with gentle babbling stream winding alongside it. Discover local highlights like Sudeley Castle, Broadway and Cheltenham Racecourse or explore the wider Cotswolds.
Popular amenities for Winchcombe house rentals
House rentals with a pool

Deluxe Coach House at Bretforton Manor with pool

Cotswolds Cottage, Heated Pool, Tithe Barn Views

Stylish Cotswolds Retreat w/ Heated Pool, Sleeps 8

43 Clearwater - family gatherings + pools + lakes

Goosewing - Cotswolds, Lakes, Family, Pools, Spa

Boundary Court Barn, Selsley common, Stroud

Rivendell, 96 Howells Mere, Lower Mill Estate

Modern contemporary home in beautiful setting
Weekly house rentals

Larch clad architect designed contemporary annexe.

The Mews House in Broadway

Astley Cottage

Attractive Period House with breath-taking views

Stone Barn, 4 bed, 4 bath Contemporary living

Meadowbrook Cottage

Beautiful 1-bedroom home in Broadway

Bourton on the Water Country Chic OldWorld Cottage
Private house rentals

Riverside Cottage • Opposite Arlington Row • Pets

Cottage on the Cotswold Way

Central Cosy Cottage with Garden & Fireplace

Large Stylish Home | Garden | Two Parking Spots

Nikolaus Cottage Winchcombe Cotswolds 2Bedrooms

Honey stone and style year round

Cotswold Stone Arts and Crafts detached house

Cosy Cotswold Cottage with Log Burner & parking
When is the best time to visit Winchcombe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,593 GYD | G$48,806 GYD | G$48,175 GYD | G$53,645 GYD | G$52,803 GYD | G$55,117 GYD | G$48,385 GYD | G$54,696 GYD | G$44,388 GYD | G$49,858 GYD | G$49,858 GYD | G$62,901 GYD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 17°C | 15°C | 11°C | 7°C | 5°C |
Destinations to explore
- Silverstone Circuit
- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- National Exhibition Centre
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- West Midland Safari Park
- Cheltenham Racecourse
- Utilita Arena Birmingham
- Cadbury World
- Ludlow Castle
- Cotswold Wildlife Park
- Coventry Building Society Arena
- University of Birmingham
- Bath Abbey
- Puzzlewood
- Sudeley Castle
- Bicester Village
- University of Warwick
- Alexander Stadium
- No. 1 Royal Crescent
- Warwick Castle
- Waddesdon Manor





