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
    Gretton, near Cheltenham×

    Windermere

    Gretton, near Cheltenham

    2
    1
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    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...

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  • Gretton, near Cheltenham
    Gretton, near Cheltenham×

    The Lodge at the Granary

    Gretton, near Cheltenham

    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...

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  • Winchcombe
    Winchcombe×

    The Barn Reborn

    Winchcombe

    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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  • Cheltenham
    Cheltenham×
    2
    1
    1
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    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 ....

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

    Stable Cottage

    Corse Lawn, near Gloucester

    2
    1
    1
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    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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  • Winchcombe, near Cheltenham
    Winchcombe, near Cheltenham×
    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...

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  • Winchcombe
    Winchcombe×
    3
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    1
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    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...

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  • Winchcombe, near Cheltenham
    Winchcombe, near Cheltenham×
    3
    2
    1
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    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...

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  • Cheltenham
    Cheltenham×

    Pavilion Mews

    Cheltenham

    4
    2
    1
    1
    Ref: NTO
    Key Features:
    - Luxury Property - Wifi - Car parking on site - Pets go free

    Pavilion Mews offers the best of both worlds; it is a short walk to the fashionable shops and restaurants...

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  • Cheltenham
    Cheltenham×

    Vivat

    Cheltenham

    4
    1
    1
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    Ref: UKC604
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Rural Location

    Vivat in Cheltenham is a lovely apartment in a quiet corner of Tivoli, within walking distance of Montpellier Gardens...

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  • Winchcombe, near Cheltenham
    Winchcombe, near Cheltenham×
    4
    2
    1
    0
    Ref: 31231
    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...

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    Your pets are included in this price
    Your pets go free at this cottage
  • Cheltenham
    Cheltenham×
    4
    2
    1
    2
    Ref: NTD
    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 ....

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    Your pets are included in this price
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