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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×

    The Lodge at the Granary

    Gretton, near Cheltenham, Gloucestershire

    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
    9.3 23 reviews

    Accommodation at

  • Cheltenham, Gloucestershire
    Cheltenham, Gloucestershire×

    Hunting Butts Cottages - Cuckoo Corner

    Cheltenham, Gloucestershire

    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
    9.1 12 reviews

    Accommodation at

    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
  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    The Barn Reborn

    Winchcombe, Gloucestershire

    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
    10 9 reviews

    Accommodation at

  • Gretton, near Cheltenham, Gloucestershire
    Gretton, near Cheltenham, Gloucestershire×

    Windermere

    Gretton, near Cheltenham, Gloucestershire

    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
    9.3 29 reviews

    Accommodation at

  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    Stable Yard Cottages - Dawn Run

    Winchcombe, Gloucestershire

    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
    7.9 13 reviews

    Accommodation at

    Stable Yard Cottages - Red Rum
    4
    1
    1
    Stable Yard Cottages - Millhouse
    4
    1
    1
  • Winchcombe, near Cheltenham, Gloucestershire
    Winchcombe, near Cheltenham, Gloucestershire×
    Newly Listed
    Rosemary Cottage

    Rosemary Cottage

    Winchcombe, near Cheltenham, Gloucestershire

    Winchcombe, near Cheltenham, Gloucestershire

    3
    2
    2
    0
    Ref: UKC2490
    Key Features:
    - Luxury Property - Wifi - Enclosed Garden / Patio - Pub within 1 mile - Garden / Patio - Woodburning Stove
    This charming, mid-terraced cottage lies in the heart of the historic and picturesque town of Winchcombe.
    Prices from
    9.8 5 reviews

    Accommodation at

  • Winchcombe, Gloucestershire
    Winchcombe, Gloucestershire×

    Stable Yard Cottages - Red Rum

    Winchcombe, Gloucestershire

    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
    7.7 3 reviews

    Accommodation at

    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

    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
    6.8 12 reviews

    Accommodation at

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

    Misty View

    Winchcombe, Cheltenham, Gloucestershire

    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
    9.5 2 reviews

    Accommodation at

  • Prestbury, near Cheltenham, Gloucestershire
    Prestbury, near Cheltenham, Gloucestershire×

    Home Farm - The Granary

    Prestbury, near Cheltenham, Gloucestershire

    Prestbury, near Cheltenham, Gloucestershire

    4
    2
    2
    0
    Ref: 7770
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile
    The Granary offers comfortable and charming accommodation; a great base to retreat to after exploring Cheltenham, the Forest of Dene and more!
    Prices from
    8.8 6 reviews

    Accommodation at

    Home Farm - The Stables
    4
    2
    2
  • Cheltenham, Gloucestershire
    Cheltenham, Gloucestershire×

    Hunting Butts Cottages - Little Barn

    Cheltenham, Gloucestershire

    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
    8.9 15 reviews

    Accommodation at

    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
  • Prestbury, near Cheltenham, Gloucestershire
    Prestbury, near Cheltenham, Gloucestershire×

    Home Farm - The Stables

    Prestbury, near Cheltenham, Gloucestershire

    Prestbury, near Cheltenham, Gloucestershire

    4
    2
    2
    0
    Ref: 7554
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Ground Floor Facilities
    This charming holiday apartment can accommodate four guests and with Cheltenham only 2 miles away, it’s a great base for exploring.
    Prices from
    9.4 12 reviews

    Accommodation at

    Home Farm - The Granary
    4
    2
    2

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