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Holiday Homes in Winchcombe, Gloucestershire

Self-Catering Holiday Cottages in Winchcombe

Experience the charm of Winchcombe with a self-catering escape in the heart of the Cotswolds. Known for its culinary delights and picturesque walking paths, it is an ideal destination for cottage holidays. Explore the historical allure of Sudeley Castle, once home to Katherine Parr, and enjoy its exquisite gardens and exhibitions. Don’t miss the Railway Museum and the beautifully preserved Gloucestershire Warwickshire Railway. For history enthusiasts, the ruins of Hailes Abbey offer a glimpse into the past with its intriguing tales. Indulge in local produce at Hayles Fruit Farm, where you’ll find fresh fruits and apple juice.

Booking your holiday accommodation in Winchcombe early is recommended for the best choice of holiday rentals.

Crop Vale Farm Lodge
Pershore, Worcestershire Around 9 miles from Winchcombe
Crop Vale Farm Lodge, Worcestershire,  England Viewed 11 times in last week.
Sleeps 1 - 4, 2 Bedroom
Weekly price: £ 512 - £ 1607
Next Available: 07/03 to 20/03/2026
Living & Leisure Facilities: woodburner Microwave Dishwasher Washing machine Garden free wifi
Type of Holiday: No dogs allowed
Beesoni Holiday Barn
Castlemorton, Worcestershire Around 14 miles from Winchcombe
Beesoni Holiday Barn, Worcestershire,  England Viewed 12 times in last week.
Sleeps 4 - 10, 4 Bedroom
Weekly price: £ 887 - £ 4538
Next Available: 30/11 to 12/12/2025
Living & Leisure Facilities: Microwave Dishwasher Washing machine Garden free wifi
Type of Holiday: 1 dogs welcome
Beautiful Cotswold View
Bourton-on-the-Water, Gloucestershire Around 10 miles from Winchcombe
Beautiful Cotswold View, Gloucestershire,  England Viewed 16 times in last week.
Sleeps 3 - 6, 3 Bedroom
Weekly price: £ 660 - £ 2824
Next Available: 01/12 to 04/12/2025
Living & Leisure Facilities: Microwave Dishwasher Washing machine Games room free wifi
Type of Holiday: No dogs allowed
Rose Cottage
Welford-on-Avon, Warwickshire Around 16 miles from Winchcombe
Rose Cottage, Warwickshire,  England Viewed 14 times in last week.
Sleeps 2 - 4, 2 Bedroom
Weekly price: £ 409 - £ 1383
Next Available: 30/11 to 19/05/2026
Living & Leisure Facilities: Microwave Dishwasher Garden free wifi
Type of Holiday: No dogs allowed
South Hill Holiday House
Stow-on-the-Wold, Gloucestershire Around 11 miles from Winchcombe
South Hill Holiday House, Gloucestershire,  England Viewed 14 times in last week.
Sleeps 11 - 22, 11 Bedroom
Weekly price: £ 4494 - £ 12920
Next Available: 07/12 to 22/12/2025
Living & Leisure Facilities: woodburner Microwave Dishwasher Washing machine Games room Garden free wifi
Type of Holiday: 2 dogs welcome Group welcome
Island Holiday Yurt
Beckford, Worcestershire Around 5 miles from Winchcombe
Island Holiday Yurt, Worcestershire,  England Viewed 12 times in last week.
Sleeps 1 - 2, 1 Bedroom
Weekly price: £ 541 - £ 2016
Next Available: 01/03 to 06/03/2026
Living & Leisure Facilities: Microwave Dishwasher Sauna free wifi
Type of Holiday: No dogs allowed
Rhydd Holiday Barn
Malvern, Worcestershire Around 16 miles from Winchcombe
Rhydd Holiday Barn, Worcestershire,  England Viewed 12 times in last week.
Sleeps 1 - 2, 1 Bedroom
Weekly price: £ 430 - £ 520
Next Available: 30/11 to 08/01/2026
Living & Leisure Facilities: Microwave Dishwasher Washing machine Balcony Garden free wifi
Type of Holiday: No dogs allowed
Epsom Cottage
Chipping Norton, Oxfordshire Around 16 miles from Winchcombe
Epsom Cottage, Oxfordshire,  England Viewed 13 times in last week.
Sleeps 3 - 5, 3 Bedroom
Weekly price: £ 1058 - £ 5919
Next Available: 07/01 to 16/02/2026
Living & Leisure Facilities: Open fire Microwave Dishwasher Washing machine Own swimming pool Garden free wifi
Type of Holiday: 1 dogs welcome
8 Bedroom Stanway House
Stow-on-the-Wold, Gloucestershire Around 9 miles from Winchcombe
8 Bedroom Stanway House, Gloucestershire,  England Viewed 13 times in last week.
Sleeps 8 - 18, 8 Bedroom
Weekly price: £ 4550 - £ 6300
Sorry this property has not provided detailed pricing information.
Living & Leisure Facilities: Microwave Dishwasher Washing machine Games room Tennis Garden BBQ
Type of Holiday: No dogs allowed Special celebrations Group welcome Weddings Corporate events
Broadway House
Stow-on-the-Wold, Gloucestershire Around 11 miles from Winchcombe
Broadway House, Gloucestershire,  England Viewed 16 times in last week.
Sleeps 7 - 16, 7 Bedroom
Weekly price: £ 3850 - £ 5775
Sorry this property has not provided detailed pricing information.
Living & Leisure Facilities: Microwave Dishwasher Washing machine Games room Tennis Garden BBQ
Type of Holiday: 2 dogs welcome Special celebrations Hen Parties Group welcome Weddings
Stanton House
Stow-on-the-Wold, Gloucestershire Around 9 miles from Winchcombe
Stanton House, Gloucestershire,  England Viewed 12 times in last week.
Sleeps 8 - 14, 6 Bedroom
Weekly price: £ 3500 - £ 5425
Sorry this property has not provided detailed pricing information.
Living & Leisure Facilities: Microwave Dishwasher Washing machine Games room Tennis Garden BBQ
Type of Holiday: 2 dogs welcome Group welcome Weddings Corporate events
Stable Cottage
Stratford-upon-Avon, Warwickshire Around 14 miles from Winchcombe
Stable Cottage, Warwickshire,  England Viewed 16 times in last week.
Sleeps 1 - 4, 2 Bedroom
Weekly price: £ 425 - £ 650
Sorry this property has not provided availability information.
Living & Leisure Facilities: coffee machine Microwave Washing machine Own swimming pool Games room Garden BBQ
Type of Holiday: No dogs allowed Special celebrations
The Shepherds Hut
Worcester, Worcestershire Around 16 miles from Winchcombe
The Shepherds Hut, Worcestershire,  England Viewed 12 times in last week.
Sleeps 1 - 2, 1 Bedroom
Weekly price: £ 540 - £ 540
Sorry this property has not provided availability and detailed pricing information.
Living & Leisure Facilities: Garden BBQ free wifi
Type of Holiday: No dogs allowed Special celebrations
Parlour at Crop Vale Farm
Pershore, Worcestershire Around 9 miles from Winchcombe
Parlour at Crop Vale Farm, Worcestershire,  England Viewed 9 times in last week.
Sleeps 1 - 2, 1 Bedroom
Weekly price: £ 470 - £ 1405
Next Available: 08/12 to 13/12/2025
Living & Leisure Facilities: woodburner Dishwasher Washing machine Garden free wifi
Type of Holiday: No dogs allowed
Greyhound Barn
Cirencester, Gloucestershire Around 15 miles from Winchcombe
Greyhound Barn, Gloucestershire,  England Viewed 10 times in last week.
Sleeps 8 - 17, 8 Bedroom
Weekly price: £ 1987 - £ 7729
Next Available: 15/12 to 18/12/2025
Living & Leisure Facilities: Dishwasher Washing machine Garden
Type of Holiday:  dogs welcome Group welcome
Pennylands Willow Lodge
Evesham, Worcestershire Around 7 miles from Winchcombe
Pennylands Willow Lodge, Worcestershire,  England Viewed 9 times in last week.
Sleeps 2 - 4, 2 Bedroom
Weekly price: £ 565 - £ 1741
Next Available: 01/12 to 05/12/2025
Living & Leisure Facilities: Dishwasher Washing machine Garden free wifi
Type of Holiday:  dogs welcome
Secret Island Yurt
Tewkesbury, Gloucestershire Around 5 miles from Winchcombe
Secret Island Yurt, Gloucestershire,  England Viewed 10 times in last week.
Sleeps 1 - 2, 1 Bedroom
Weekly price: £ 577 - £ 2170
Next Available: 10/04 to 05/06/2026
Living & Leisure Facilities: Sauna free wifi
Type of Holiday: No dogs allowed


Cottages, Apartments & Lodges in Winchcombe, Gloucestershire, England

CountryCottagesOnline.Net features holiday home(s) within or close to Winchcombe, enjoy browsing through the available options. We hope you find the perfect holiday house for you in Winchcombe, Gloucestershire.


Self-Catering Breaks in Winchcombe, Cotswolds

Winchcombe, nestled in the heart of the Cotswolds, is known for its fine cuisine and is a great place to stop for lunch. The countryside surrounding Winchcombe is crisscrossed with walkers' paths and trails, often discovered by people during rambles from Hailes and Sudeley.

Exploring Sudeley Castle in Winchcombe

Sudeley Castle has enjoyed royal patronage since the 10th century and is a beloved tourist attraction. Tudor Sudeley Castle, once home to Katherine Parr, one of the wives of Henry VIII, offers gardens to explore, a restaurant for refreshments, and a Tudor costume exhibition.

Visit the Railway Museum in Winchcombe

The Railway Museum is a fascinating destination, especially for those interested in railway machinery and engineering. The Gloucestershire Warwickshire Railway line runs steam and diesel trains. Dubbed the ‘Friendly Line in the Cotswolds,’ it offers a 20-mile round trip from Toddington to Cheltenham Racecourse, including the 693-yard Greet Tunnel.

Hayles Fruit Farm in Winchcombe

Lord Sudeley planted an orchard in 1880, which is now the thriving Hayles Fruit Farm. Visitors can pop into the farm shop for a wide range of pressed apple juice and fresh fruit, and enjoy a meal at the restaurant.

Discover Hailes Abbey near Winchcombe

Anyone interested in myths and religious traditions should visit the ruins of the 1246 AD Cistercian Hailes Abbey. It was once a place of pilgrimage because of a supposed phial of Christ's blood, endorsed with a papal guarantee. The site includes a small museum and a shop.

What Does Winchcombe Offer for Cottage Breaks?

Winchcombe is an ideal location for cottage breaks, allowing visitors to enjoy the area's historical sites, beautiful countryside, and culinary delights at their own pace. Whether exploring Sudeley Castle, visiting local farms, or enjoying the scenic train rides, Winchcombe provides a delightful and serene retreat in the Cotswolds.

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