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Holiday Cottages in Winchcombe

A stay in the stunning market town of Winchcombe allows you to enjoy the Cotswolds at its finest. Savour fresh local produce, browse several independent shops, soak up the beautiful countryside and stroll along the meandering River Isbourne. Discover a fascinating world of history and centuries-old architecture or simply unwind with a drink in hand when you book a break in one of our Cotswold holiday cottages in Winchcombe. Read more

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51.952174, -1.966467

A charming stone holiday cottage ideally situated in the lovely market town of Winchcombe in the heart of the North Cotswold's with excellent eating establishments and amenities on the doorstep. A great self-catering base for exploring Central England and its many attractions.

Weekly guide price:
£850 to £1050
Short breaks from £130 per night

4  |   2  |   3+  |   Yes  |   Yes

Min nights: 3 (off peak) | 3 (peak)

Preferred arrival day: Flexible

51.980867, -2.007171

You'll fall asleep as soon as your head hits the pillow when you stay at The Lodge. After a full day of walking, cycling, horseriding and sightseeing, the quiet location and comfortable king-sized bed will welcome you home. The one-bedroom cottage is ideal for couples or solo travellers, including those who want to bring their dog, horse or bike to explore the huge network of footpaths, bridleways and cycling routes that spread across the Cotswolds, linking beautiful views with pretty villages and towns that make this part of the country a favourite in every season.

Weekly guide price:
£300 to £585
Short breaks from £65 per night

2  |   1  |   2  |   Enquire  |   Yes

Min nights: 3 (off peak) | 7 (peak)

Preferred arrival day: Mon/Fri

51.963586, -1.913420

With spectacular views in all directions, The Old Stables is a perfect holiday cottage for people who love long countryside walks. The Cotswold Way passes nearby, and Hailes Abbey, Sudeley Castle and Winchcombe are within a few miles. It's impossible to decide whether the Cotswolds are more beautiful in spring, summer, autumn or winter. Still, with holiday bookings available all year round and short breaks possible, you can stay at The Old Stables in any season and enjoy being close to Cheltenham, Broadway, and Stow-on-the-Wold, and less than an hour from Blenheim Palace and Stratford-Upon-Avon. With self-catering accommodation for four people in two bedrooms with two bathrooms, there is ample room for couples, families or friends.

Weekly guide price:
£450 to £550
Short breaks from £95 per night

4  |   2  |   2  |   Yes  |   Yes

Min nights: 3 (off peak) | 3 (peak)

Preferred arrival day: Flexible

51.955130, -1.964105

How can you resist staying in this charming Cotswold cottage? Windsor Cottage is just steps away from Winchcombe High Street with its great pubs like the Plaisterers Arms and the Lion Inn, shops and restaurants. The property can sleep up to four and is popular with families or couples who want the benefit of staying in a pretty village without being overrun by tourists. The Cotswold Way and Gloucestershire Way are just two of seven waymarked footpaths that run through the village, which is a short drive or cycle from well known Cotswold places including Cheltenham, Stow-on-the-Wold, Chipping Campden and Broadway. Sudeley Castle is nearby, and the village has a good local museum and lovely church with interesting features. Staying at Windsor Cottage is a wonderful way to experience the charm of the Cotswolds in comfort, with the convenience of a central location in a village favoured by locals but as yet undiscovered by day trippers.

Weekly price:
£775 all year
Short breaks from £95 per night

4  |   2  |   1  |   Yes  |   Yes

Min nights: 3 (off peak) | 3 (peak)

Preferred arrival day: Mon/Fri

52.046335, -1.887956

"Little Padley" is a 1 bed holiday Cottage sleeping up to 2 guests in Worcestershire. Broadway, 'The Jewel of the Cotswolds,' is a picturesque village located in Worcestershire. This picturesque village in the heart of the Cotswolds is not only home to some of the best independent stores, art galleries, and restaurants in the...

Prices from £120 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.935161, -1.683902

"Stable Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. The highest town in the Cotswolds, Stow-on-the-Wold, originally an Iron Age Fort, epitomises olde worlde England. This ancient market town has played host to many fairs since the 12th century and today holds a biannual Gypsy Horse Fair, craft...

Prices from £184 per night

4  |   2  |   Yes  |   Yes  |   Yes


51.867286, -1.786437

"Foxhill Farm Barn" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Located in the Cotswold Area of Outstanding Natural Beauty, the historic village of Bourton-on-the-Water dates back to Neolithic times with over 100 buildings being Grade II listed or higher. The picturesque high street nestles alongside the...

Prices from £164 per night

2  |   1  |   No  |   Yes  |   Yes


51.969220, -2.256670

"Garden Cottage - One-Bedroom Holiday Home" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. This holiday home's standout feature is the fireplace. Featuring a private entrance, this holiday home is comprised of 1 bedroom and 1 bathroom with a shower. The holiday home's kitchen, which has kitchenware, is available for cooking and...

Prices from £125 per night

2  |   1  |   No  |   Yes  |   Yes


51.944800, -2.036000

"Bungalow in Gloucestershire" is a 2 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. The village of Woodmancote enjoys an enviable location with the Regency Spa town of Cheltenham on its doorstep and a wealth of walking from your front door including Cleeve Hill, with well waymarked paths that will take you across this...

Prices from £231 per night

2  |   2  |   Yes  |   Yes  |   Yes


52.014328, -1.761241

"Cottage in Gloucestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. This charming cottage is located in the heart of popular Blockley, a delightful village located in the heart of the Cotswolds. Blockley embodies the quintessential Cotswolds charm with its honey coloured limestone cottages, winding streets and...

Prices from £246 per night

2  |   1  |   Yes  |   Yes  |   Yes


52.112099, -1.960555

"Chadbury House Annexe" is a 1 bed holiday Cottage sleeping up to 2 guests in Worcestershire. Evesham is a picturesque market town resting in the Vale of Evesham amidst the beautiful River Avon in Worcestershire. In easy reach of Cheltenham, Worcester and Stratford-upon-Avon, there's plenty of excitement to explore within the local...

Prices from £138 per night

2  |   1  |   Yes  |   Yes  |   Yes


52.024563, -2.031886

"The Lakeside Yurt" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Beckford is a small riverside village on the Worcestershire/Gloucestershire border. The village has a quality country inn, an attractive Norman church, and a nature reserve. Close by is Evesham, and elegant Cheltenham is also an easy drive...

Prices from £201 per night

2  |   1  |   Yes  |   Yes  |   No


52.088055, -1.858633

"Cotswold View 4" is a 1 bed holiday Lodge sleeping up to 2 guests in Worcestershire. The charming village of Honeybourne lies in an ideal position within the Worcestershire countryside, within reaching distance of the magnificent Cotswolds Area of Outstanding Beauty. Boasting a handy supermarket, quintessential Post Office and...

Prices from £254 per night

2  |   1  |   No  |   Yes  |   Yes


52.053681, -1.870785

"Glencoe Cottage" is a 3 bed holiday Cottage sleeping up to 5 guests in Worcestershire. Willersey lies in the Cotswolds on the Gloucestershire/Worcestershire border. It ha 2 pubs, a shop and is 2 miles from Broadway. The Cotswold Way, Heart of England Way and Monach's Way walking paths are close by. Broadway, known as 'The Jewel...

Prices from £189 per night

5  |   3  |   Yes  |   Yes  |   Yes


52.038412, -1.732400

"The Old Mission Church, Paxford, near Chipping Campden" is a 2 bed holiday Lodge sleeping up to 4 guests in Gloucestershire. On entering the property, guests will be wowed by the designer kitchen with its large central island, flowing into the living and dining areas. The church is packed with original features including original doors, stained-glass windows, vaulted...

Prices from £399 per night

4  |   2  |   Yes  |   Yes  |   Yes


51.930042, -1.721547

"April Cottage (Stow), Stow-on-the-Wold" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. Additional photography to follow.April Cottage is a comfortable, welcoming and well-equipped cottage located in the centre of the hugely popular Cotswold market town of Stow-on-the-Wold, an ideal base to explore all the Cotswolds has to...

Prices from £204 per night

4  |   2  |   No  |   Yes  |   Yes


52.045954, -1.964992

"Ross Cottage" is a 2 bed holiday Cottage sleeping up to 3 guests in Worcestershire. The pretty market town of Evesham lies within the Vale of Evesham, in a horseshoe of the River Avon, within driving distance of Worcester, Cheltenham and Stratford-upon-Avon. Evesham and the surrounding area is famous for its market gardening...

Prices from £160 per night

3  |   2  |   Yes  |   Yes  |   Yes


52.011119, -1.765178

"Alice Cottage" is a 2 bed holiday Cottage sleeping up to 3 guests in Gloucestershire. An ancient village once famous for its silk and corn mills, Blockley lies just 3 miles from Moreton-in-Marsh and features a unique collection of honey-coloured buildings with a pretty village green, two excellent pubs, serving hearty food and...

Prices from £160 per night

3  |   2  |   Yes  |   Yes  |   Yes


51.954607, -1.962765

"Fern Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. Winchcombe is a Cotswold town, found in Gloucestershire lying above the River Isbourne. It is home to beautiful timbered inns, independent shops and businesses, with fresh local produce available to buy to prepare some delicious food on your...

Prices from £233 per night

4  |   2  |   Yes  |   Yes  |   Yes


52.005125, -1.904471

"The Old Cider Press" is a 2 bed holiday Cottage sleeping up to 4 guests in Worcestershire. Stanton is arguably one of the prettiest and most idyllic villages in the whole of the Cotswolds, located at the foot of the Shenberrow Hill in the Northern reaches of the Cotswolds. Without doubt it has one of the most stunning high streets in...

Prices from £210 per night

4  |   2  |   No  |   Yes  |   Yes


51.847400, -2.040700

"Barn in Gloucestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Upper Coberley is a small hamlet of cottages set within established farmlands. Well positioned for walkers with easy access to The Cotswold Way, where you can join the pathway going south towards Leckhampton Hill and north towards Dowdeswell....

Prices from £277 per night

2  |   1  |   No  |   Yes  |   Yes


52.093280, -1.792380

"The Apple Loft - One-Bedroom Holiday Home" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Boasting a private entrance, this holiday home comes with 1 bedroom, 1 bathroom and a kitchen. The holiday home's kitchen, which has a dishwasher and kitchenware, is available for cooking and storing food. This holiday home features heating and...

Prices from £152 per night

2  |   1  |   No  |   Yes  |   Yes


51.957050, -1.962280

"The Barn Reborn - Nrp - One-Bedroom Holiday Home" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. This holiday home features a fireplace. Featuring a private entrance, this holiday home comprises 1 bedroom and 2 bathrooms with a shower. The holiday home's kitchen, which features a dishwasher and kitchenware, is available for cooking and...

Prices from £315 per night

2  |   1  |   No  |   Yes  |   Yes


51.916216, -2.050022

"3 Lake Cottages" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. The village of Prestbury rests on the edge of Cheltenham, surrounded by Gloucestershire countryside. The village boasts amenities including a shop and a Post Office, pubs and a butcher. Prestbury Park, home to Cheltenham Racecouse, is below the...

Prices from £196 per night

2  |   1  |   No  |   Yes  |   Yes


51.907200, -1.848300

"Barn in Gloucestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. The unspoilt village of Naunton is tucked peacefully away in the heart of a valley though just off the main tourist trail. Well served with a traditional village pub, a historic dovecote situated in a beautiful spot by the river Windrush, along...

Prices from £283 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.962000, -1.742800

"Cottage in Gloucestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. This quintessential Cotswold dormer cottage nestles into a hillside and enjoys panoramic views across the sweeping hills and valleys of the North Cotswolds. The renowned Longborough Festival Opera is situated virtually underneath the stepped...

Prices from £341 per night

2  |   1  |   Yes  |   Yes  |   Yes


51.881100, -2.133240

"Cottage in Gloucestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Offering spacious and stylish interior that seamlessly blends rustic charm with modern amenities, providing a cosy yet elegant retreat, nestled amidst beautifully landscaped gardens, dog friendly and perfect for couples. Set off the beaten...

Prices from £198 per night

2  |   1  |   Yes  |   Yes  |   Yes


52.031627, -2.114830

"The Coach House Apartment" is a 1 bed holiday Apartment sleeping up to 2 guests in Gloucestershire. Bredon is a quiet village in Worcestershire close to the Cotswolds Area of Outstanding Natural Beauty at the foot of Bredon Hill, home to a convenience store, two village pubs, a and a takeaway, as well as a tranquil marina and National Trust...

Prices from £127 per night

2  |   1  |   No  |   Yes  |   Yes


Cottages in Winchcombe

Spend your holiday in Winchcombe curled up by the open fire reading your favourite book or embark on a hike across the fields right from your doorstep. Our cottages come with a range of features to suit your needs — from spacious dog-friendly gardens to luxe hot tubs. There are also numerous charming Cotswold villages to explore within easy reach of Winchcombe. Or, why not simply take a stroll down the high street and treat yourself to coffee and a piece of cake?

From dining in traditional pubs tucked away behind Cotswold stone exteriors to exploring Sudeley Castle and taking a ride on the Gloucestershire Warwickshire Steam Train, there really is plenty to do when you plan a getaway to this corner of England. So, why not book your perfect Winchcombe holiday cottage today and get planning your next escape?

Best things to do in Winchcombe

Whether you fancy mooching around the shops, refuelling with some food or exploring the many nearby trails on foot, bike or with the dog, there’s plenty to do in Winchcombe.

  • Sudeley Castle: Absorb a bit of history as you wander through the award-winning gardens and beautifully restored rooms of this historical castle.
  • Belas Knap Long Barrow: Discover this English Heritage site on Cleeve Hill which features a neolithic, chambered long barrow.
  • Winchcombe Museum: Explore, learn and discover the heritage of Winchcombe and its surrounding areas with a wander around the Winchcombe Museum.
  • Hailes Abbey: Uncover the ruins of a 13-century Cistercian abbey set amid the peaceful Cotswold countryside.
  • Gloucester Cathedral: Discover over 1,300 years of history, including the Tomb of the King. The cathedral stands proud over Gloucester and Harry Potter fans will instantly recognise it from the film series.

How to get to Winchcombe

If you’re travelling from one of the major cities in the UK, the below shows an average distance to Winchcombe, so you know what to expect when choosing to visit by car.

London: 114 miles

Birmingham: 60 miles

Glasgow: 334 miles

Liverpool: 143 miles

Bristol: 56 miles

Manchester: 131 miles

Leeds: 158 miles

Edinburgh: 336 miles

Newcastle: 245 miles

More locations in the Cotswolds

The Cotswolds is made up of several quintessentially English villages with honey-coloured stone buildings and pretty rural locations. Want to see more of the area? Here are five more locations to consider for your next holiday cottage: