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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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  • 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. Cuckoo Corner is a wonderful romantic retreat, offering a cosy woodburner and rural views.
    Prices from
    8.8 18 reviews
    8.8 18 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
    Walnut Tree House
    14
    5
    5
  • 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. Perfect for walkers, with paths, cycle paths and bridleways from the door, Cheltenham Racecourse is within easy reach.
    Prices from
    9.1 15 reviews
    9.1 15 reviews

    Accommodation at

  • 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 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 15 reviews
    10 15 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:
    - Wifi - 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. Situated in the Cotswold countryside, there are great footpaths to enjoy from this characterful yet stylish property, perfect for a romantic getaway.
    Prices from
    9.4 34 reviews
    9.4 34 reviews

    Accommodation at

  • Cheltenham, Gloucestershire
    Cheltenham, Gloucestershire×
    Newly Listed
    The Gallery

    The Gallery

    Cheltenham, Gloucestershire

    Cheltenham, Gloucestershire

    2
    1
    1
    1
    Ref: UKC2933
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Garden / Patio
    This lovely property is located on the edge of Cheltenham and is ideal for those looking to explore Gloucestershire and the Cotswolds. This lovely property is located on the edge of Cheltenham and is ideal for those looking to explore Gloucestershire and the Cotswolds.
    Prices from
    10 1 reviews
    10 1 reviews

    Accommodation at

  • Winchcombe, Gloucestershire Gloucestershire
    Winchcombe, Gloucestershire Gloucestershire×

    Dawn Run

    Winchcombe, Gloucestershire Gloucestershire

    Winchcombe, Gloucestershire 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. This holiday property is situated in a peaceful setting, yet is also within easy reach of the market town of Winchcombe.
    Prices from
    7.7 9 reviews
    7.7 9 reviews

    Accommodation at

    Stable Yard Cottages - Arkle
    6
    2
    2
  • 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. This charming, mid-terraced cottage lies in the heart of the historic and picturesque town of Winchcombe.
    Prices from
    9.4 19 reviews
    9.4 19 reviews

    Accommodation at

  • 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 - Garden / Patio - Ground Floor Facilities - Rural Location
    A perfect location for anyone interested in horse racing, Cheltenham and its race course is just 5 miles away. A perfect location for anyone interested in horse racing, Cheltenham and its race course is just 5 miles away.
    Prices from
    6.2 12 reviews
    6.2 12 reviews

    Accommodation at

    Stable Yard Cottages - Arkle
    6
    2
    2
  • 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! The Granary offers comfortable and charming accommodation; a great base to retreat to after exploring Cheltenham, the Forest of Dene and more!
    Prices from
    9 4 reviews
    9 4 reviews

    Accommodation at

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

    Pavilion Mews

    Cheltenham, Gloucestershire

    Cheltenham, Gloucestershire

    4
    2
    1
    1
    Ref: NTO
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio
    Fashionable shops and restaurants are a short walk from this beautiful holiday property, or visit the Cotswold villages of Stow-on-the-Wold and Winchcombe. Fashionable shops and restaurants are a short walk from this beautiful holiday property, or visit the Cotswold villages of Stow-on-the-Wold and Winchcombe.
    Prices from
    8.6 29 reviews
    8.6 29 reviews

    Accommodation at

  • Great Witcombe, near Birdlip, Gloucestershire
    Great Witcombe, near Birdlip, Gloucestershire×

    Witcombe Estate - Peats Cottage

    Great Witcombe, near Birdlip, Gloucestershire

    Great Witcombe, near Birdlip, Gloucestershire

    4
    2
    1
    3
    Ref: 28415
    Key Features:
    - Car parking on site - Pub within 1 mile - Pets go free - Rural Location - Open Fire
    Set on a working farm, this delightful cottage has a lovely location with views and is great for exploring the Cotswold towns. Set on a working farm, this delightful cottage has a lovely location with views and is great for exploring the Cotswold towns.
    Prices from
    7.2 10 reviews
    7.2 10 reviews

    Accommodation at

    Witcombe Estate - Jaffa Cottage
    5
    3
    3
  • 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. Boasting a four poster bed, this cosy cottage is ideally situated to explore Cheltenham or Stratford-upon-Avon.
    Prices from
    7.7 3 reviews
    7.7 3 reviews

    Accommodation at

    Stable Yard Cottages - Arkle
    6
    2
    2

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