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.

A Cotswold Farm Barn Conversion within a walled garden
Nellie's Barn
Bourton-on-the-Water
Gloucestershire
England
Sleeps
4
Bedrooms
2

Boasting Cotswolds yellow stone and exposed beams, Nellie’s Barn is a blend of charm and sophistication. The pet-friendly holiday cottage near Bourton-on-the-Water sits on a farm in the Windrush Valley and offers delightful gardens, on-site fishing, a summer house, a wood burner and countryside walks from the front door.

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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 wood and slate Cotswold holiday cottage overlooks a terrace with dining table and lawn.
The Sycamore, Bibury
Bibury
Gloucestershire
England
Sleeps
2
Bedrooms
1

Couples seeking a relaxing getaway will enjoy a stay at The Sycamore, a delightful romantic Cotswold holiday cottage for couples near the historic village of Arlington in Gloucestershire. It's the perfect weekend retreat featuring plenty of natural light streaming from double-height windows, beamed ceilings, and wood floors.

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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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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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Second Nature, Cheltenham
Cheltenham
Gloucestershire
England
Sleeps
2
Bedrooms
1

Enjoy a romantic Cotswolds holiday with a stay at Second Nature on the outskirts of the spa town of Cheltenham, Gloucestershire, the perfect getaway for couples wanting to explore this picturesque region. Second Nature is an eco-friendly rural retreat for two boasting a distinctive four-poster bed and walk-in rain shower.

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Exterior of a large, 3-storey, brick-built Wye Valley cottage with a large lawn.
Forest House, Gloucestershire
Coleford
Gloucestershire
England
Sleeps
24
Bedrooms
11

Forest House is a spacious holiday cottage located in Coleford, situated in the heart of the picturesque Forest of Dean. This property was formerly a 4-star hotel but is now converted into a self-catering accommodation that is perfect for large groups of holidaymakers who wish to explore the surrounding area. With 11 bedrooms, it can comfortably accommodate up to 24 guests.

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A jasmine-clad, semi-detached, traditional Cotswold 'honeystone' country cottage.
Jasmine Cottage
Windrush
Gloucestershire
England
Sleeps
3
Bedrooms
2

Jasmine Cottage is a cute 300-year-old Cotswold stone cottage nestled in the idyllic village of Windrush in Oxfordshire. The pet-friendly cottage is surrounded by National Trust land and boasts an inglenook fireplace, a hand-built kitchen and flagstone floors, a lovely garden and a log fire.Escape to the idyllic village of Windrush in Oxfordshire and experience the charm of Jasmine Cottage, a 300-year-old Cotswold stone cottage. Surrounded by National Trust land, this pet-friendly cottage offers the perfect retreat with its cozy inglenook fireplace, stunning hand-built kitchen with flagstone floors, lovely garden and inviting log fire. Book your stay now and indulge in the peace and tranquility of this charming cottage.

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Cotswold cottage exterior with a bay window and low stone garden wall.
Hope Cottage (Quenington)
Quenington
Gloucestershire
England
Sleeps
6
Bedrooms
3

Hope Cottage epitomises Cotswold charm. The stone-built, luxury rural retreat near Cirencester in Gloucestershire offers a lovely country garden with impressive views and open-plan spaces with contemporary design features, exposed beams, French doors, natural light and a cosy wood-burning stove.

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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