The patio garden and exterior of a Gloucestershire holiday cottage, with outdoor dining table and a hammock strung between trees.. Endless Esther, A Large Gloucestershire Holiday Let in the Severn Valley.

Find My Favourite Holiday Cottages in Gloucestershire

To relax and enjoy self-catering holidays in the idyllic and historic County of Gloucestershire, do so in comfort and style by renting a self-catering cottage for a weekend, a whole week or even longer. There are many parts to Gloucestershire: the historic towns of Gloucester and Cheltenham, The Cotswold Hills, The Forest of Dean and the valleys of the Severn and the Wye all having their own distinctive appeal. You won't find yourself short of stunning views and memorable experiences.

You'll find castles such as those at Berkeley and Sudeley and achingly beautiful villages such as the two Upper and Lower Slaughters, Stow-on-the-Wold, Chipping Campden or Boughton on the Water, all seemingly unchanged for centuries. There's even a Roman villa at Chedworth; while just digging anywhere in the market town of Cirencester, Roman remains will be revealed. Make sure you visit the elegant Georgian spa town, Cheltenham, with its magnificent Pump-rooms, rivalling those in Bath.

Aerial view of a contemporary farm house surrounded by open fields.
Willersey Farm House in The Cotswolds
Broadway
Gloucestershire
England
Sleeps
8
Bedrooms
4

Set in its own gated grounds, Willersey Farm House is a large holiday cottage in the Cotswolds. It is a unique blend of old and new, with a traditional Cotswold house housing the bedrooms attached to an all-new, contemporary living area. Traditional beams and honey-stone walls mix with stunning contemporary design to create an exceptional Warwickshire country cottage near Broadway.

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Exterior of a large, 3-storey, Wye Valley holiday home.
River Wye Lodge
Lydbrook
Gloucestershire
England
Sleeps
24
Bedrooms
12

River Wye Lodge is a spacious holiday cottage in the Forest of Dean overlooking the picturesque River Wye. The cottage can accommodate up to 26 guests, and it is easily accessible. You can spend your days exploring the Forest and theWye Valley or enjoy a variety of activities on the river. Alternatively, you can relax in the cottage's hot tub, games room, or children's playground. Pets are welcome to join you on your holiday.

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The Anchor in Lydbrook
Lydbrook
Gloucestershire
England
Sleeps
22
Bedrooms
8

Once a village pub, The Anchor has been tastefully converted to create a large Forest of Dean Holiday Cottage, complete with a hot tub and games room. This family-friendly holiday home in Gloucestershire lies in a magical rural location in the Wye Valley. Pets welcome.

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Exterior of a double-fronted Cotwolds honey-stone cottage
Alysas Cottage, Chipping Norton
Chipping Norton
Gloucestershire
England
Sleeps
5
Bedrooms
3

Charming Alysas Cottage sits on the grounds of a mixed working farm just outside the West Oxfordshire market town of Chipping Norton; a wonderful three-bedroom child-friendly cottage in the Cotswolds, it has been refurbished to a high standard while retaining original features such as oak doors and lofty beamed ceilings.

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Large Windermere holiday cottage on a terrace overlooking a spacious lawn.
Cleabarrow Cottage, Bowness-on-Windermere
Draycott
Gloucestershire
England
Sleeps
12
Bedrooms
6

Cleabarrow Cottage is an impressive rural holiday cottage offering large groups seclusion, luxury and a hot tub. Generous lawned grounds surround the property in Windermere, Cumbria, and offer beautiful countryside views, while the interior and exterior promise elegant spaces in which to relax and entertain.

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Exterior of a single-storey with a conservatory having sliding glass doors overlooking a spacious garden.
The Garden Studio
Bournes Green
Gloucestershire
England
Sleeps
2
Bedrooms
1

Escape to The Garden Studio, an idyllic and romantic holiday cottage in the serene hamlet of Bournes Green, Gloucestershire. Impeccably presented and surrounded by the stunning Cotswold countryside, this sophisticated rural retreat offers the perfect blend of traditional charm and modern comfort. Relax in the pretty garden, soak up the sun in the bright and airy sunroom, or unwind on your own private patio. This is the ultimate destination for a romantic getaway or a peaceful retreat. Book your Gloucestershire cottage holiday at The Garden Studio today and experience the beauty of the Cotswolds like never before.

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A brick-built 1930s cottage with covered porch and block-paved courtyard.
2 The School House, Dorsington
Dorsington
Gloucestershire
England
Sleeps
4
Bedrooms
2

2 The School House is an attractive 1930s semi-detached property situated in the peaceful village of Dorsington, 7 miles from Stratford-upon-Avon. Conveniently located on the border of Warwickshire and the Cotswolds, it is the ideal base to discover Shakespeare Country.

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A wisteria clad, semi-detached Cotswold country cottage overlooks a shingled courtyard
October Cottage
Chalford
Gloucestershire
England
Sleeps
4
Bedrooms
2

Surrounded by fields and woodland in Chalford, Gloucestershire, October Cottage promises tranquillity. The charming stone-built rural cottage in the Cotswold Hills possesses beautiful gardens and fresh air, a wood-burning stove, flagstone floors, contemporary comforts, space for pets and a blend of old and new.

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A Cotswold holidy cottage with a vine-covered exterior.
The 99 Yew Trees, Painswick
Painswick
Gloucestershire
England
Sleeps
6
Bedrooms
3

The 99 Yew Trees is a gorgeous 3-bedroom holiday cottage in Painswick overlooking the church in the heart of The Cotswolds. The 16th-century townhouse boasts a lavish garden full of mature plants and a neutral palette accentuated by traditional features such as the fireplace, wood burner, exposed beams and stone walls.

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Visit the city of Gloucester and the 1000-year-old Norman Cathedral, whose role in history embraces the mediaeval tomb of Edward the II through to its 21st-century use as a location for Harry Potter Films (Hogwarts) and Dr Who. 

A little further up the M5 is the fine Regency Spa town of Cheltenham. Here you’ll be spoiled for choice of restaurants and cultural experiences. Cheltenham is a festival town with major UK music, literature, jazz and folk events. To see Cheltenham from the air, a balloon flight over the city has to be one of the best ways to travel. There are festivals aplenty in Gloucestershire, attracting visitors from all over the world. In addition to the many festivals held throughout the year in Cheltenham, the Tewkesbury Medieval Festival is also a crowd-puller. It features the largest annual medieval battle in the UK - a re-enactment of the 1471 Battle of Tewkesbury. The festival is fought by thousands of people and witnessed by many more. See it! 

Many quaint traditional events, such as the Cheese Rolling every May at Coopers Hill, are worth a weekend break. Here men, women and children take it in turns to run hurly-burly down a steep hill in Brockworth near Gloucester chasing a large circular cheese. You have to see it to believe it!

Talking of cheese, locally grown produce isn’t hard to find in the County with its plethora of excellent delicatessens and farmers’ markets. If you’re staying in a self-catering holiday cottage, this will ensure you feast like Royalty every evening during your holiday. You can work off dinner the following day at a choice of adrenalin-filled activity centres, such as kayaking in the Cotswold Water Park or The High Ropes Centre in the Forest of Dean. Putting food to one side, if you stop off at the Thames Head Inn, you’ll be sitting right next to the source of the River Thames.

The Forest of Dean, an Area of Outstanding Natural Beauty bordering the picturesque Wye Valley, is well worth visiting. It offers miles of footpaths and cycle trails through beautiful woodland. Walk the inspirational sculpture trail or view it from the carriage window of a steam train courtesy of Dean Forest Rail, whose 8 miles of track take you through the forest near Lydney. You can even travel along trails through the Forest of Dean by Segway near Parkend.

If you have a penchant for chocolate villages, tea rooms, antique shops and historic architecture, then you will love the Cotswolds. A large part of Gloucestershire is Cotswold Country, where visitors can choose beautifully restored and furnished holiday cottages. Here there are walks a plenty, such as the Stanton, Snowshill and Edge Walk – 6 miles over hills and down wooded dales with 3’ chocolate box’ villages and a choice of tea rooms.

Spend a day or two enjoying the selection of activities at The Cotswold Country Park & Beach near Cirencester – a water park with swimming, water zorbing, adventure playgrounds, kayaking and lovely lakeside walks. A string of cosy villages and small towns hug the banks of The River Servern, such as Tewkesbury, where the ancient Tewkesbury Abbey is open to the public, and Upton-on-Severn hosts some notable music festivals during the summer. 

The River Severn offers excellent opportunities for fishermen and those happy to spend an hour or so on the water by hiring a boat. While on the watery theme, visitors will enjoy a day at the Slimbridge Wild Life Water Park, a UK Visitor Attraction of the Year. Lakes, pools, and ponds bristle with a spectacular variety of wetland birds: ducks, geese, swans and even flamingos. Some are resident all year round, while others arrive for the summer or winter. Walk around or take a canoe safari.

As you can see, a short break or more extended self-catering holiday in Gloucestershire will give you, your friends and your family a memorable and relaxing experience, whichever part of the County you choose to call your home during your stay.

Gloucestershire Destinations