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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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51.980867, -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

51.952174, -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

51.963586, -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:
£480 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

51.833945, -2.193124

"Bond End Farm Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Nestled within the rural village of Upton St. Leonards, a beautifully renovated old Cotswold stone apple barn. The village itself is in an ideal location, with Painswick Beacon (2.5 miles), Painswick Rococo Gardens (3.0 miles), and Kites Hill...

Prices from £255 per night

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51.931392, -1.723563

"Coln Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Once an Iron Age Fort, the ancient market town of Stow-on-the-Wold is the highest town in the Cotswolds. Home to a traditional market square decorated with Cotswold stone townhouses, the town homes a selection of shops and eateries, including...

Prices from £158 per night

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51.992635, -2.155218

"The Old Paper Shop" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Found on the meeting of the rivers Severn and Avon, the town of Tewkesbury is rich with history and medieval character with its half timbered buildings and home to over 350 listed buildings. The town has a wealth of shops to offer, both local...

Prices from £112 per night

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51.806456, -1.921358

"Brooklands" is a 2 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Chedworth is an attractive historic village in Gloucestershire. The village is home to one of the largest Roman villas in Britain. Outdoor enthusiasts will enjoy the excellent scenic walks from the village including The Monarch’s Way and The...

Prices from £136 per night

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51.928398, -1.745787

"Cottage in Gloucestershire" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. This beautiful cottage is in the village of Lower Swell, nestled in the picturesque Cotswold countryside. The Cotswolds provides a tranquil and scenic setting for a holiday where you will be able to immerse yourself in the natural beauty of the...

Prices from £263 per night

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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 £144 per night

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51.876300, -2.136400

"Barn in Gloucestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. The peaceful hamlet of Badgeworth is surrounded by countryside, with a wealth of walking from your front door, along with the Regency Spa town of Cheltenham on its doorstep. This central location offers easy access for touring the larger...

Prices from £218 per night

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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 £152 per night

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52.095617, -2.129146

"The Old Piggery" is a 1 bed holiday Cottage sleeping up to 2 guests in Worcestershire. Defford is a small village on the edge of Bredon Hill in Worcestershire's Heritage Garden, one of England's most unspoiled places, known for its Blossom Trail and locally grown fruit and vegetables. A short drive away is Pershore, a beautiful...

Prices from £142 per night

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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 £161 per night

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52.041600, -1.986940

"Orchard Farm Retreat" is a 1 bed holiday Cottage sleeping up to 2 guests in Worcestershire. This spacious, one-bedroom property lies within the Evesham Vale on the edge of the charming Worcestershire village of Ashton under Hill. Surrounded by countryside and set on the fringes of the Cotswolds National Landscape, this is a delightful...

Prices from £149 per night

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52.052591, -1.778035

"Lanes Cottage" is a 2 bed holiday Cottage sleeping up to 3 guests in Gloucestershire. This market town defines the saying "good things come in small packages" as it proves itself to be a wonderful place for tourists to stay. Chipping Campden sits in the northern part of the Cotswolds and boasts many historical buildings from St....

Prices from £147 per night

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52.050787, -1.780789

"The Cottage" is a 3 bed holiday Cottage sleeping up to 5 guests in Gloucestershire. This market town defines the saying "good things come in small packages" as it proves itself to be a wonderful place for tourists to stay. Chipping Campden sits in the northern part of the Cotswolds and boasts many historical buildings from St....

Prices from £174 per night

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52.049200, -1.784300

"Cottage in Gloucestershire" is a 3 bed holiday Cottage sleeping up to 5 guests in Gloucestershire. Located in the heart of bustling Chipping Campden, this is an excellent choice for guests wishing to bid farewell to four wheels for a while. Set out on foot to browse the town s abundance of boutique shops, cafes and galleries, or sample some...

Prices from £200 per night

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52.076100, -1.795800

"Cottage in Gloucestershire" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. The peaceful village of Aston Subedge is a wonderful example of countryside living in the Cotswolds with stunning views in an idyllic setting. The National Trust property Dover s Hill is 2 miles away and can be reached on foot by joining up...

Prices from £241 per night

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51.929251, -1.716752

"Holly Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in Gloucestershire. Stow-on-the-Wold, the highest town in the Cotswolds, was originally an Iron Age Fort and is a perfect example of traditional English life. Since the 12th century, this historic marketplace has hosted a variety of fairs, including the biennial...

Prices from £166 per night

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51.780061, -2.032983

"Five Mile House Barn" is a 3 bed holiday Cottage sleeping up to 6 guests in Gloucestershire. Cirencester is a market town resting on the edge of the Cotswolds aonb, just 15 miles away from Cheltenham. Within the busy town you will find a number of shops and eateries, as well as attractions including the Corinium Museum which displays a...

Prices from £165 per night

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51.993677, -2.158616

"The Coach House" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. On the confluence of the Rivers Severn and Avon, this historic riverfront town retains its mediaeval charm with many half-timbered Tudor structures. With more than 350 buildings that are recognised as being of historic interest and located in a...

Prices from £139 per night

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52.078472, -2.027518

"Barn in Worcestershire" is a 1 bed holiday Cottage sleeping up to 2 guests in Worcestershire. This wonderful rural retreat is located in a quiet and peaceful village in the picturesque Worcestershire countryside, perfect for a relaxing break away. The village is surrounded by fields and rolling hills, providing visitors with plenty of...

Prices from £158 per night

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52.009786, -2.083312

"Beechnut Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. The village of Northway can be found nestled in the luscious Gloucestershire countryside and boasts an array of local shops, a charming pub and a well-thought supermarket stocking all of the household essentials. There are an array of scenic...

Prices from £108 per night

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51.935161, -1.683902

"Well Cottage" is a 1 bed holiday Cottage sleeping up to 2 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 £155 per night

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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 £150 per night

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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

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52.005040, -2.162045

"Avonmede" is a 1 bed holiday Cottage sleeping up to 2 guests in Gloucestershire. Located at the meeting of the rivers Severn and Avon, this picturesque town has managed to preserve its mediaeval charm while gaining an abundance of Tudor-style half-timbered structures. Tewkesbury is home to approximately 350 historic...

Prices from £170 per night

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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: