
House holiday rentals in Winchcombe
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Top-rated house rentals in Winchcombe
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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.

Iconic 17th Century Thatched Cottage
Enjoy the beautiful garden in the summer sunshine or hunker down next to the fire in the winter, Hoo Cottage has it all! It is one of the few thatched Cotswold Stone properties, tucked away in the idyllic village of Chipping Campden. We have done our best to bringing out the distinctive character of this historic property, while furnishing it in a luxurious rustic style. The history of the cottage is still up to debate. However, we have found evidence of it playing a role as the village bakery.

Breathtaking Cotswold Renovated 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).

Almsbury Farmhouse, Sudeley Castle, Cotswolds
Almsbury Farmhouse is a beautifully restored property that sleeps 14 guests across 3 double bedrooms, 3 twin bedrooms and a separate self-contained annexe with a double bed. The main farmhouse is arranged over 3 floors, with a large dining room and table to seat 14, well-equipped kitchen, cosy sitting room, snug/breakfast room, playroom, and five bathrooms (including annexe en-suite) with additional downstairs WC. Almsbury Farmhouse is perfect for larger groups or families looking to relax.

Beautiful 4 bed house in Cotswolds
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.

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.

Larch clad architect designed contemporary annexe.
Relax at this unique and tranquil getaway in the beautiful South Cotswolds. The Annexe is a separate dwelling next to an architecturally award winning contemporary house located in a quiet village. The larch clad property has an industrial, boho meets the Cotswold vibe with its own private wild flower garden, perfect for alfresco dining. Excellent location for walking, running and cycling. Close to the beautiful town of Cirencester, idyllic picturesque villages and gastro pubs galore!

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.

Riverside Cottage • Opposite Arlington Row • Pets
Escape to Sackville House —a beautiful riverside, Grade II-listed Cotswold haven. Located in the heart of Bibury, you're just 140 yards from iconic Arlington Row and steps from the tranquil River Coln. This rare, pet-friendly retreat that sleeps 6, blends authentic historic charm with modern luxury, including a dreamy roll-top bath under the eaves. Enjoy river views, a private terrace, and free parking nearby. The perfect base for exploring the Cotswolds' most beautiful village.

Magical cottage set within a woodland glade
Badgers Bothy is set within a woodland glade in the grounds of the 16th century Amberley Farmhouse and provides the most unique and charming country escape. Our idyllic cottage is set on the edge of Minchinhampton Common (located in an AONB) and with miles of footpaths which are perfect for those wishing to explore the Cotswolds. This beautiful cottage exudes an aura of peace and tranquillity and a haven for those wishing to escape the hustle and bustle of a busy life.

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
Popular amenities for house rentals in Winchcombe
House rentals with a pool

100 Howells Mere - 100HM - Lakeside Spa Property

Cotswold Celebrations and Gatherings. Heated Pool

Lakeside | Hot Tub | Pools & Spa | Lower Mill

Boundary Court Barn, Selsley common, Stroud

Deluxe Coach House at Bretforton Manor with pool

Stylish Cotswolds Retreat w/ Heated Pool, Sleeps 8

Cotswolds Cottage, Heated Pool, Tithe Barn Views

43 Clearwater - Lower Mill Estate + Pools + Spa
Weekly house rentals

Regency Coach House Cheltenham

Cotswold Stone Arts and Crafts detached house

Boutique cottage in the heart of Winchcombe

Period Cotswold Cottage near Cotswold Way

Honey stone and style year round

Cosy Cotswold Cottage with Log Burner & parking

Modern & stylish family home | private garden

The Room Next Door- Boutique room in the Cotswolds
Private house rentals

Charming cottage

Elegantly presented - The Garden House

Smart Luxury Character Cottage @ Stow on the Wold

The Assembly Hall

Campden Cottage

Hill View

18th Century Cotswolds Cottage | Parking | Garden

Lavender Cottage Cotswold Farm Retreat
When is the best time to visit Winchcombe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $319 SGD | $296 SGD | $292 SGD | $331 SGD | $285 SGD | $255 SGD | $294 SGD | $332 SGD | $270 SGD | $303 SGD | $303 SGD | $382 SGD |
| 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 |
Quick stats about house rentals in Winchcombe

Total holiday rentals
Explore 50 holiday rentals in Winchcombe

Nightly prices starting at
Winchcombe holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 2,010 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Winchcombe holiday rentals include wifi 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!
Destinations to explore
- Cottage rentals Winchcombe
- Rentals with a fireplace Winchcombe
- Rentals with outdoor seating Winchcombe
- Pet-friendly rentals Winchcombe
- Rentals with a patio Winchcombe
- Family-friendly rentals Winchcombe
- Rentals with a washing machine and dryer Winchcombe
- Rentals with a firepit Winchcombe
- House rentals Gloucestershire
- House rentals England
- House rentals United Kingdom
- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Utilita Arena Birmingham
- Silverstone Circuit
- Cheltenham Racecourse
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- West Midland Safari Park
- Cadbury World
- Bath Abbey
- Ludlow Castle
- Sudeley Castle
- Waddesdon Manor
- University of Warwick
- No. 1 Royal Crescent
- National Exhibition Centre
- Puzzlewood
- Coventry Cathedral
- Eastnor Castle
- Coventry Building Society Arena
- Dyrham Park
- Hereford Cathedral
- Bowood House and Gardens





