by Wyndham Vacation Rentals
Shortlist

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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47 cottages are available
  • 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

    Situated at Lower Stanley, in the peaceful village of Gretton, this is the ideal location to enjoy the local...

    Prices from
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    Pets included
    Pets go free
  • 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

    Set within the Cotswold countryside, with outstanding views towards Dumbleton Hill and the Malverns, this delightful...

    Prices from
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    Pets included
    Pets go free
  • Corse Lawn, near Gloucester ,
    Corse Lawn, near Gloucester , ×

    Stable Cottage

    Corse Lawn, near Gloucester ,

    2
    1
    1
    0
    Ref: 28027
    Key Features:
    - Pub within 1 mile - Detached Property - Rural Location

    Located in beautiful Gloucestershire countryside, on a working farm with glorious views over the Malvern Hills,...

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    Pets included
    Pets go free
  • 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

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

    Prices from
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    Pets included
    Pets go free
  • 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 delightful, timber framed barn is situated within the grounds of Grade II listed Charingworh Court, which...

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    Pets included
    Pets go free
  • Winchcombe, near Cheltenham, Gloucestershire
    Winchcombe, near Cheltenham, Gloucestershire×

    Sudeley Castle Country Cottages - Charles I

    Winchcombe, near Cheltenham, Gloucestershire

    3
    2
    1
    1
    Ref: 31230
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile

    Sudeley Castle Country Cottages are the ideal choice for a walking or touring holiday, or simply as an escape into...

    Prices from
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    Pets included
    Pets go free
  • 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

    Peaceful, picturesque location

    Situated just outside the beautiful Cotswold market town of Winchcombe, Stable...

    Prices from
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    Pets included
    Pets go free
  • Winchcombe, near Cheltenham, Gloucestershire
    Winchcombe, near Cheltenham, Gloucestershire×

    Sudeley Castle Country Cottages - St Kenelm

    Winchcombe, near Cheltenham, Gloucestershire

    3
    2
    1
    0
    Ref: 31232
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile

    Sudeley Castle Country Cottages are the ideal choice for a walking or touring holiday, or simply as an escape into...

    Prices from
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    Pets included
    Pets go free
  • 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

    Peaceful, picturesque location

    Situated just outside the beautiful Cotswold market town of Winchcombe, Stable...

    Prices from
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    Pets included
    Pets go free
  • Winchcombe, near Cheltenham, Gloucestershire
    Winchcombe, near Cheltenham, Gloucestershire×

    Sudeley Castle Country Cottages - Anne Boleyn

    Winchcombe, near Cheltenham, Gloucestershire

    4
    2
    1
    1
    Ref: 31227
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio

    Sudeley Castle Country Cottages are the ideal choice for a walking or touring holiday, or simply as an escape into...

    Prices from
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    Pets included
    Pets go free
  • 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

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

    Prices from
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    Pets included
    Pets go free
  • Great Witcombe, near Birdlip, Gloucestershire
    Great Witcombe, near Birdlip, Gloucestershire×

    Witcombe Estate - Peats Cottage

    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

    These two holiday cottages (refs 28414, 28415) are located on a working farm and form part of the 400-year-old...

    Prices from
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    Pets included
    Pets go free

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