48 hours in Cheltenham and Cotswolds suggested itinerary

Inspire Me

  1. Suggested Cheltenham itineraries
    Looking for some inspiration to help plan your stay in Cheltenham? These suggested itineraries will help you to discover the unmissable highlights of the most Regency town in Britain and hidden gems, loved by locals.
  2. What's On in Cheltenham
    The most comprehensive Cheltenham 2025 what's on guide ft. the best things to do and events in Cheltenham, Cotswolds and Gloucestershire. Use our interactive event finder to help.
  3. Things To Do in Cheltenham
    Looking for things to do in Cheltenham? Get the latest information on attractions, activities, tours & sightseeing, shopping in Cheltenham and more.
  4. Restaurants and bars in Cheltenham
    Choose one of our many places to eat and drink in Cheltenham, whether it's coffee and cake, a bite to eat at lunch or dinner and cocktails...
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Highlights

Vine & Orchard Adventures

Vine & Orchard Adventures

Sister brand to Tivoli Wines, Cheltenham’s leading independent wine merchant, Vine & Orchard…

The Slaughters

The Slaughters

Two picturesque villages situated on the tiny River Eye.

Eat Sleep Axe Cheltenham

Eat Sleep Axe

An urban axe throwing venue that provides a fun, friendly environment for you to hang out with…

Afternoon tea at The Find

The Find

An extraordinary coffee house serving artisan coffees and beverages, superb foods and delicacies of…

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Number of results: 148

, currently showing 1 to 20.

  1. Add Sudeley Castle & Gardens to your Itinerary

    Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 2118 review(s)from 2118 review(s)

    Sudeley Castle & Gardens

    Type

    Type:

    Castle/Fort

    Winchcombe, Near Cheltenham

    Dates

    From:
    17 Mar 2025to2 Nov 2025Open 10:00 - 17:00

    Award-winning gardens surrounding Castle and medieval ruins. Exhibitions, castle rooms, gift shop & cafes, the best adventure play fort in Gloucestershire!

  2. Add Gloucestershire Warwickshire Steam Railway to your Itinerary

    Gloucestershire Warwickshire Steam Railway

    Type

    Type:

    Steam Railway

    Winchcombe, Cheltenham

    Dates

    From:
    2 Mar 2025to1 Jan 2026Various Opening Times

    The friendly line in the Cotswolds offers a unique opportunity to sample train travel from 50 years ago...

  3. Add The Brewery Quarter to your Itinerary

    The Brewery Quarter

    Type

    Type:

    Food & Drink

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Open 09:00 - 00:00

    The Brewery Quarter prides itself on being a 'one-stop shop where you can shop-dine-stay and play!' Here you'll find many much-loved venues including Son of Steak, Hollywood Bowl, Escape Hunt, The Alchemist, The Botanist, Cineworld and many more!

  4. Add Tour and Explore to your Itinerary

    Tour and Explore

    Type

    Type:

    Guided Tour

    Gloucester

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Tour and Explore

    We provide informative and entertaining Tour Guides for coach & walking tours of North Wiltshire and the Cotswolds. There’s so much to see - medieval villages, magnificent abbeys & churches, ancient monuments, attractive gardens

  5. Add C-Side Spa to your Itinerary

    Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 102 review(s)from 102 review(s)

    C-Side Spa

    Type

    Type:

    Hotel Spa

    Near Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Bathed by the natural beauty of the Cotswold countryside. A haven for self-care, a tonic for the soul. Welcome back to the C-Side Spa, where our team offers a range of holistic therapies including massages, facials and exfoliating wraps plus…

  6. Add Cheltenham Playhouse Theatre to your Itinerary

    Cheltenham Playhouse Theatre

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Welcome to Cheltenham Playhouse Theatre; an intimate community theatre set in a Regency period building.

  7. Add Dryhill Cottage & Vineyard to your Itinerary

    Dryhill Cottage & Vineyard

    Type

    Type:

    Food & Drink

    Ullenwood, Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Set within the breathtaking Cotswolds, only five miles from the beautiful Regency town of Cheltenham, Dryhill Cottage & Vineyard is a tranquil retreat offering panoramic views that stretch over 50 mile and delicious homegrown wine.

  8. Add Events and Experiences at John Lewis & Partners Cheltenham to your Itinerary

    Events and Experiences at John Lewis & Partners Cheltenham

    Type

    Type:

    Event Venue

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Offering a variety of bookable services, visitors to John Lewis Cheltenham can book a Personal Styling appointment, Nursery Advice service or a Home Design consultation.

  9. Add Montpellier Gardens to your Itinerary

    Montpellier Gardens

    Type

    Type:

    Garden

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Montpellier Gardens lie close to the town centre and are an important part of Cheltenham's regency landscape. The gardens can be split into two recreational zones.

  10. Add Pittville Park to your Itinerary

    Pittville Park

    Type

    Type:

    Municipal Park

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    A fantastic blend of living history, open spaces, children's activities and of course a boating lake! The perfect place to spend a day...

  11. Add The Promenade and Long Gardens to your Itinerary

    The Promenade and Long Gardens

    Type

    Type:

    Garden

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Cheltenham's famous Promenade dates back to 1818 at the height of the Regency period, when the avenue of elms and horse chestnut trees was first planted.

  12. Add Pittville Pump Room to your Itinerary

    Pittville Pump Room

    Type

    Type:

    Historic Site

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Pittville Pump Room is a beautiful, historic Grade One listed property set in parkland at Pittville used for cultural, commercial and community events.

  13. Add Montpellier Caryatids to your Itinerary

    Montpellier Caryatids

    Type

    Type:

    Sub-Attraction

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Don't miss Cheltenham's most iconic Regency feature; The Caryatids in Montpellier.

  14. Add The Centaur to your Itinerary

    The Centaur

    Type

    Type:

    Venue Provider

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Located in the heart of England at Cheltenham Racecourse,The Centaur has room for 2,250 people to sit, more than 4,000 to stand and 1,200 to have a gourmet banquet.

  15. Add Cheltenham Town Hall to your Itinerary

    Cheltenham Town Hall

    Type

    Type:

    Historic Site

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Cheltenham Town Hall is now home to an impressive all year round programme of major festivals, entertainment, exhibitions and functions. Built in 1902-1903 as a venue for social events, it replaced the Assembly Rooms on the High Street, which had…

  16. Add Leisure At Cheltenham to your Itinerary

    Leisure At Cheltenham

    Type

    Type:

    Leisure/Swimming Pool

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    With such a large range of activities available at Leisure At Cheltenham, there really is something for everyone, from swimming to racket sports, soft play and even trampolining.

  17. Add The Boathouse Activities (Boat Hire, Tennis, Pitch & Putt), Pittville Park to your Itinerary

    The Boathouse Activities (Boat Hire, Tennis, Pitch & Putt), Pittville Park

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Open 10:00 - 17:00

    The Boathouse is the place to hire rowing boats plus book pitch & putt golf and tennis courts. You can also plus purchase fishing licenses from here.
    The Boathouse organise their own events for children and families including Welly Walks and nature…

  18. Cox's Meadow

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Cox’s Meadow is a mixture of wetland and wildland. Since the early years of the millennium it has been part of Cheltenham’s Flood Alleviation Scheme. The town is vulnerable to floods caused by run-offs from thunderstorms high on the nearby hills.

  19. Add Holst Victorian House to your Itinerary

    Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 182 review(s)from 182 review(s)

    Holst Victorian House

    Type

    Type:

    Museum

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Explore life in Cheltenham’s only Victorian home open to all, the birthplace of composer Gustav Holst in 1874.

  20. Tripadvisor Traveller Rating

    Tripadvisor Traveller Rating - from 11 review(s)from 11 review(s)

    Cotswold Discovery Trail

    Type

    Type:

    Self-Guided Tour

    Stroud

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Treasure trails to explore the beauty, history and heritage of the Cotswolds. Have fun exploring the Cotswolds by car following trail directions and answering questions and clues.

Statues