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Cheltenham

Cheltenham lies at the western gateway to the Cotswolds and is famous for its Georgian architecture, Regency terraces and elegant, sophisticated ambience. It became a fashionable spa town in the 18th Century and the medicinal waters helped to elevate the town to a tourist resort, attracting both royalty and the aristocracy.

Nowadays, Cheltenham is a thriving market town full of boutique shops, restaurants, bars, and cafes and is ideally situated for exploring the surrounding Cotswold countryside. The town features many listed buildings with period terraces and garden squares in typical regency style. In spring, the town bursts into colour with floral displays and there are numerous gardens and parks in which to enjoy a relaxing stroll.

Cheltenham is known as ''the festival town of England,'' hosting an array of prestigious events, including the world famous Cheltenham Gold Cup (Horse race). There are also numerous other events throughout the year including jazz, folk, science, food, comedy and literary festivals. There are theatres, art galleries and museums, including the town''s newest attraction, ‘The Wilson’, housing fine art collections and works by local artists.

Shopping is a big feature in the town, and there are numerous award-winning independent shops, including antique shops, specialist boutiques and family-run delicatessens, specialising in Gloucestershire cheeses and other excellent local produce. On the second and last Friday of each month, a farmers'' market sets up stalls outside the main Tourist Centre, providing more opportunities to sample local foods.

Come and discover a town packed with regency charm on the edge of the Cotswolds; search holiday cottages in Cheltenham today.
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  • Gretton, near Cheltenham, Gloucestershire
    Gretton, near Cheltenham, Gloucestershire×

    Windermere

    Gretton, near Cheltenham, Gloucestershire

    2
    1
    1
    2
    Ref: 28228
    Key Features:
    - Car parking on site - Enclosed Garden / Patio - Pets go free - Garden / Patio - Rural Location
    Situated in the Cotswold countryside, there are great footpaths to enjoy from this characterful yet stylish property, perfect for a romantic getaway.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Set within the Cotswold countryside, with outstanding views towards Dumbleton Hill and the Malverns, this delightful barn conversion, adjacent to the owners’ home, is a perfect holiday location. The property is situated just a few miles from the market town of Winchcombe and the elegant Regency town of Cheltenham, with its internationally famous racecourse. There are a wealth of footpaths in the area to suit all tastes and abilities. Places of interest close by include Sudeley...

  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    The Barn Reborn

    Winchcombe, Gloucestershire

    2
    1
    2
    0
    Ref: NRP
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Detached Property - Garden / Patio - Woodburning Stove
    This spacious detached barn, dating from 1650, adjacent to the owners’ home in Winchcombe, is the perfect base for exploring the Cotswolds AONB
    Prices from
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    Pets included
    Pets go free

    Accommodation at


    This delightful, timber framed barn is situated within the grounds of Grade II listed Charingworh Court, which dates back to the 17th century - a year before Charles II claimed the throne. Now, it provides 21st century comforts, following an architect-designed transformation. Exceptionally spacious, but cosy too, The Barn Reborn is set in a quiet backwater away from traffic, and is the perfect place to unwind in and enjoy a relaxing break in the Cotswolds Area of Outstanding...

  • Cheltenham, Gloucestershire
    Cheltenham, Gloucestershire×

    Hunting Butts Cottages - Cuckoo Corner

    Cheltenham, Gloucestershire

    2
    1
    1
    0
    Ref: NYM
    Key Features:
    - Wifi - Swimming pool - Car parking on site - Pub within 1 mile
    Cuckoo Corner is a wonderful romantic retreat, offering a cosy woodburner and rural views.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    "Fine cottages and facilities – just a mile from one of England’s finest Regency towns . . ."

    Occupying a superb position with wonderful rural views, yet within a mile or so of Cheltenham’s elegant town centre, these delightful holiday cottages have been created from a range of 19th-century barns and are furnished and equipped to high standards. All cottages enjoy a good choice of shared facilities including a covered heated swimming pool,...

    Hunting Butts Cottages - The Dovecote
    5
    2
    2
    Hunting Butts Cottages - Little Barn
    4
    2
    2
    Hunting Butts Cottages - Owl’s Retreat
    4
    2
    2
    Hunting Butts Cottages - Woodpecker
    6
    3
    3
    Hunting Butts Cottages - Thistledown
    6
    3
    3
    Hunting Butts Cottages - Swallow End
    7
    3
    3
    Hunting Butts Cottages - Wheathill
    6
    3
    3
    Hunting Butts Cottages - Walnut Tree House
    14
    5
    5
  • Gretton, near Cheltenham, Gloucestershire
    Gretton, near Cheltenham, Gloucestershire×

    The Lodge at the Granary

    Gretton, near Cheltenham, Gloucestershire

    2
    1
    1
    2
    Ref: 27326
    Key Features:
    - Wifi - Car parking on site - Pets go free - Garden / Patio - Rural Location
    Perfect for walkers, with paths, cycle paths and bridleways from the door, Cheltenham Racecourse is within easy reach.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Situated at Lower Stanley, in the peaceful village of Gretton, this is the ideal location to enjoy the local landscape. Perfect for walkers, there are numerous paths, bridleways and cycle paths from the door. The Lodge is attached to the owners’ house but provides privacy and space. Explore Winchcombe, Bourton-on-the-Water, Broadway, Chipping Campden and Evesham. For a day at the races, Cheltenham Racecourse is within easy reach. Stabling and grazing for horses by arrangement. Shop...

  • Corse Lawn, near Gloucester , Gloucestershire
    Corse Lawn, near Gloucester , Gloucestershire×

    Stable Cottage

    Corse Lawn, near Gloucester , Gloucestershire

    2
    1
    1
    0
    Ref: 28027
    Key Features:
    - Pub within 1 mile - Detached Property - Rural Location
    Situated in Gloucestershire, this property is ideally placed for the Regency town of Cheltenham, known as the gateway to the Cotswolds.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Located in beautiful Gloucestershire countryside, on a working farm with glorious views over the Malvern Hills, this detached holiday property is ideally placed for walking and perfect for exploring the numerous historic gardens nearby. Situated in Gloucestershire but lying close to the border with Worcestershire and Herefordshire, the area is renowned for its scenic countryside and outstanding walking, especially along the Severn Valley and Malvern Hills. The Cotswold Hills and the...

    Corse Hill Farm Cottages - Holly Cottage
    2
    1
    1
  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    Stable Yard Cottages - Dawn Run

    Winchcombe, Gloucestershire

    3
    0
    1
    0
    Ref: 19073
    Key Features:
    - Car parking on site - Pub within 1 mile - Detached Property - Garden / Patio - Rural Location
    This holiday property is situated in a peaceful setting, yet is also within easy reach of the market town of Winchcombe.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Peaceful, picturesque location

    Situated just outside the beautiful Cotswold market town of Winchcombe, Stable Yard Cottages are a group of three well presented holiday cottages and a studio apartment, in a peaceful location. Ideally placed for touring the Cotswolds and the many picturesque towns and villages including Broadway, Chipping Campden, Stow-on-the-Wold and Moreton-in-Marsh. Cheltenham and its race course are just 5 miles away, while Tewkesbury and Stratford-upon-Avon are...

    Stable Yard Cottages - Red Rum
    4
    1
    1
    Stable Yard Cottages - Millhouse
    4
    1
    1
  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    Stable Yard Cottages - Red Rum

    Winchcombe, Gloucestershire

    4
    1
    1
    0
    Ref: 19071
    Key Features:
    - Car parking on site - Pub within 1 mile - Ground Floor Facilities - Rural Location
    Boasting a four poster bed, this cosy cottage is ideally situated to explore Cheltenham or Stratford-upon-Avon.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    Peaceful, picturesque location

    Situated just outside the beautiful Cotswold market town of Winchcombe, Stable Yard Cottages are a group of three well presented holiday cottages and a studio apartment, in a peaceful location. Ideally placed for touring the Cotswolds and the many picturesque towns and villages including Broadway, Chipping Campden, Stow-on-the-Wold and Moreton-in-Marsh. Cheltenham and its race course are just 5 miles away, while Tewkesbury and Stratford-upon-Avon are...

    Stable Yard Cottages - Millhouse
    4
    1
    1
    Stable Yard Cottages - Dawn Run
    3
    0
    0
  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    Stable Yard Cottages - Millhouse

    Winchcombe, Gloucestershire

    4
    1
    1
    1
    Ref: 19072
    Key Features:
    - Car parking on site - Pub within 1 mile - Pets go free - Ground Floor Facilities - Rural Location
    A perfect location for anyone interested in horse racing, Cheltenham and its race course is just 5 miles away.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    Peaceful, picturesque location

    Situated just outside the beautiful Cotswold market town of Winchcombe, Stable Yard Cottages are a group of three well presented holiday cottages and a studio apartment, in a peaceful location. Ideally placed for touring the Cotswolds and the many picturesque towns and villages including Broadway, Chipping Campden, Stow-on-the-Wold and Moreton-in-Marsh. Cheltenham and its race course are just 5 miles away, while Tewkesbury and Stratford-upon-Avon are...

    Stable Yard Cottages - Red Rum
    4
    1
    1
    Stable Yard Cottages - Dawn Run
    3
    0
    0
  • Badgeworth, near Cheltenham, Gloucestershire
    Badgeworth, near Cheltenham, Gloucestershire×

    The Lodge

    Badgeworth, near Cheltenham, Gloucestershire

    4
    2
    1
    2
    Ref: 30803
    Key Features:
    - Car parking on site - Pets go free - Detached Property - Ground Floor Facilities
    This single-storey holiday property is the ideal base for visiting Cheltenham, Gloucester, Worcester and Hereford.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    The Lodge is a 2 bedroomed, single-storey, detached bungalow, situated on the edge of Cheltenham in Badgeworth. It is situated within the grounds of the owner’s home where you have access to 2 acres of communal grounds to enjoy. It is the ideal holiday location, and is close to pretty Cotswolds towns and villages, including Broadway, Stow-on-the-Wold and Moreton-in-Marsh. The market towns of Tewkesbury and Ledbury are only a short drive away, as are the cathedral cities of...

  • Toddington, near Winchcombe, Gloucestershire
    Toddington, near Winchcombe, Gloucestershire×
    Newly Listed
    Meadow Cottage

    Meadow Cottage

    Toddington, near Winchcombe, Gloucestershire

    4
    2
    1
    1
    Ref: UKC1665
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Garden / Patio
    Explore the many beautiful villages of the Cotswolds and its stunning scenic Cotswold walks. Broadway, Chipping Campden, Winchcombe and Bourton-on-the-Water are all close by.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at


    Meadow Cottage is a delightful, end-terrace holiday cottage, situated in the Cotswold village of Toddington. Just 3 miles away is Winchcombe’s town centre, which has excellent pubs and restaurants, as well as good food shops and many independent stores. It has also achieved ’Welcome Walkers’ status meaning it is all geared up to provide excellent facilities, public transport and easy access to footpaths. Whether you want to walk, cycle or drive, Meadow Cottage is...

  • Winchcombe, Cheltenham, Gloucestershire
    Winchcombe, Cheltenham, Gloucestershire×

    Misty View

    Winchcombe, Cheltenham, Gloucestershire

    4
    2
    2
    0
    Ref: NV7
    Key Features:
    - Wifi
    History enthusiasts will love this cosy cottage just minutes away from Sudeley Castle home to Queen Catherine Parr.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at


    This modern Cotswold stone cottage lies close to the heart of the delightful town of Winchcombe. Adjoining another property, it is set along a quiet lane, 2 minutes’ walk from an excellent range of shops, historic pubs, restaurants and beautiful Sudeley Castle (once home of a Queen and venue of Liz Hurley’s wedding). There are many picturesque old villages to explore, lively market towns, as well as Regency Cheltenham, Bath and Stratford-upon-Avon. There is fine walking...

  • Cheltenham, Gloucestershire
    Cheltenham, Gloucestershire×

    Hunting Butts Cottages - Little Barn

    Cheltenham, Gloucestershire

    4
    2
    1
    2
    Ref: NTC
    Key Features:
    - Wifi - Swimming pool - Car parking on site - Pub within 1 mile
    This rurally located holiday cottage is ideally located for family activities in Cheltenham or amongst the property’s surrounding grounds.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    "Fine cottages and facilities – just a mile from one of England’s finest Regency towns . . ."

    Occupying a superb position with wonderful rural views, yet within a mile or so of Cheltenham’s elegant town centre, these delightful holiday cottages have been created from a range of 19th-century barns and are furnished and equipped to high standards. All cottages enjoy a good choice of shared facilities including a covered heated swimming pool,...

    Hunting Butts Cottages - The Dovecote
    5
    2
    2
    Hunting Butts Cottages - Owl’s Retreat
    4
    2
    2
    Hunting Butts Cottages - Cuckoo Corner
    2
    1
    1
    Hunting Butts Cottages - Woodpecker
    6
    3
    3
    Hunting Butts Cottages - Thistledown
    6
    3
    3
    Hunting Butts Cottages - Swallow End
    7
    3
    3
    Hunting Butts Cottages - Wheathill
    6
    3
    3
    Hunting Butts Cottages - Walnut Tree House
    14
    5
    5
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