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 coach house conversion with tall trees behind and a lawn in front.
Sleeps
5
Bedrooms
3

The Coach House is an authentic rural holiday cottage in Gloucestershire on the beautiful grounds of a Grade II-listed 16th-century Old Rectory. The cottage in the little Cotswold village of Hawling near Cheltenham dates back to the 14th century and boasts stunning views over meadows, an open fire, luxurious décor and perfectly located for walking holidays in the Cotswold Hills.

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Exterior of a terraced Cotswold holiday cottage overlooking a village street.
Sleeps
4
Bedrooms
1

The Cotswold Cedar is a sophisticated and romantic 2-bedroom holiday cottage near Painswick set on the grounds of a 16th-century house. The Cotswold stone cottage is gorgeously presented and offers a pleasant sun-trap garden with a furnished deck, bi-fold doors and

open-plan spaces promising total relaxation.

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A brick-built 1930s cottage with covered porch and block-paved courtyard.
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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Large Windermere holiday cottage on a terrace overlooking a spacious lawn.
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 small Gloucestershire cottage and adjoining stable in a garden.
Sleeps
2
Bedrooms
1

Elinor Fettiplace is a rustic romantic cottage on the grounds of Elizabethan Pauntley Court. Sitting near Pauntley in Gloucestershire, it dates back to the 1300s and boasts beamed ceilings, wooden floors, and authentic rural charm. A tennis court and lakes are found on the extensive grounds.

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Sleeps
16
Bedrooms
8

Once a hop brewery, this 15th-Century Grade-II listed barn has been converted to create a large and attractive Cotswold holiday cottage in an idyllic rural village near Cirencester. Greyhound Barn sleeps 16 guests in 8 bedrooms (all en-suite). Pets welcome.

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A Cotswold holidy cottage with a vine-covered exterior.
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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Stone exterior of a terraced Cotswold cottage with a paved garden having a table and chairs.
Sleeps
2
Bedrooms
1

6 Mount Pleasant is a charming, romantic cottage perfect for couples, located in the heart of the picturesque Cotswold village of Blockley, Gloucestershire. This beautiful yellow stone cottage features exposed beams and stone walls, offering a unique blend of elegance and cosy spaces. The cottage is equipped with a log fire, providing a warm and inviting atmosphere, and a sun-drenched patio that allows you to soak up the beautiful surroundings. The cottage is also ideally located for exploring the Cotswolds.

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A glimpse of the rooftop and 1st floor of a country cottage surrounded by woods and fields.
Sleeps
8
Bedrooms
3

Endless Esther is a characterful eco-friendly cottage nestled among nature near Hewelsfield Common in Gloucestershire. The pet-friendly cottage boasts upcycled materials and features a generous garden, a courtyard with hammocks, exposed stone walls and beams, a log fire, and a sauna.

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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.