Holiday rentals in Winchcombe

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

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.

Detached Annex in idyllic Countryside

Separate annex in idyllic countryside location, beautiful walks, local country pub. Near to Croome Court National Trust. Close to M5 and M50. Self Catering private location. The annex is prepared to a high standard and we respect your privacy leaving you to enjoy your stay. The annex has a free sat TV, fully fitted kitchen, tea, coffee and milk are provided along with a selection of biscuits, fluffy white towels, and a comfy new bed. The sofa can convert to a double bed if required. Free WIFI.

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).

Vineyard cosy cottage near Ledbury, Herefordshire

Hop cottage, a lovely cosy self catering cottage set perfectly on the edge of the vines. The cottage features double bedroom with en-suite. Spacious living area is ideal for people needing to work - The twin room on the second floor has a sloping roof and due to steep stairs is not suitable for children under 8 Coddington Vineyard is close to the market town of Ledbury and the Malvern hills are 15 mins away ideal for walking and cycling. A complimentary wine tasting for guests at week ends.

Cotswold Cottage (Superking & Double) With Garden

Your home away from home and the perfect base to explore the area or just enjoy being part of the Cotswolds :) Full of character and charm with exposed beams and stone walls throughout, Honey Cottage is the perfect Cotswold retreat in the heart of the historical town of Winchcombe. There is also a lovely large, enclosed, private garden and patio area with views to the picturesque church, BBQ, outdoor dining area & sofa. Both the kitchen and the double bedroom have views over the garden.

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.

The Feathered Nest an idyllic Cotswolds escape.

Nestled in the heart of historic Winchcombe, The Feathered Nest offers a welcoming escape in the beautiful North Cotswolds. Set on picturesque Vineyard Street, this lovingly restored former wool cottage blends timeless character with modern comforts. Thoughtfully renovated by the owners this the boutique two-bedroom home features stylish furnishings and all the contemporary amenities you need for a relaxing stay. Available for mid week or long weekend breaks this Spring.

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

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!

'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.

2-Bed Character Cottage, Access to Cotswold Way!

Just 15 minutes by taxi or 20 minutes by direct bus to Cheltenham Racecourse, Greystones is a charming Grade II listed Cotswold cottage set in an Area of Outstanding Natural Beauty. Featuring original character, a private garden with stream, and direct access to the Cotswold Way, it’s perfect for romantic breaks, walking holidays, and peaceful countryside escapes near Cheltenham.