Filter
Property Type
Property Features
Sleeps

Holiday Homes in Cheltenham, Gloucestershire

Self-Catering Holiday Cottages in Cheltenham

Experience the best of Cheltenham on a self-catering escape, choosing between a chic town apartment or a cozy countryside cottage. This stylish spa town, nestled in the Cotswolds, boasts a rich history, stunning architecture, and vibrant cultural scenes. Don't miss the charming Montpellier area for boutique shopping and dining, or explore historic sites like Cheltenham Ladies College. For equestrian enthusiasts, the Cheltenham Gold Cup in March is a must-see. Add visits to the Holst Birthplace Museum and the Cheltenham Art Gallery to your itinerary for a well-rounded stay. Perfect for a variety of occasions, Cheltenham promises a memorable holiday.

Booking your holiday accommodation in Cheltenham early is recommended for the best choice of holiday rentals.

Stable Cottage, Warwickshire, England
Viewed 8× this week

Stable Cottage

Stratford-upon-Avon, Warwickshire ~20 miles from Cheltenham
Sleeps 1–4 2 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 21/03 to 28/03/2026
Facilities
WiFi Coffee machine Microwave Washing machine Pool Games room Garden BBQ
Type of Holiday
No dogs allowed Special celebrations
Epsom Cottage, Oxfordshire, England
Viewed 17× this week

Epsom Cottage

Chipping Norton, Oxfordshire ~19 miles from Cheltenham
Sleeps 3–5 3 Bedrooms 🐾 1 Dog
Next Available 24/03 to 27/03/2026
Facilities
WiFi Open fire Microwave Dishwasher Washing machine Pool Garden Parking
Type of Holiday
1 dogs welcome
Rhydd Holiday Barn, Worcestershire, England
Viewed 11× this week

Rhydd Holiday Barn

Malvern, Worcestershire ~16 miles from Cheltenham
Sleeps 1–2 1 Bedroom 🚫 No Dogs
Next Available 21/03 to 10/04/2026
Facilities
WiFi Microwave Dishwasher Washing machine Balcony Garden Parking
Type of Holiday
No dogs allowed
The Barn, Worcestershire, England
Viewed 18× this week No booking fee

The Barn

Worcester, Worcestershire ~18 miles from Cheltenham
Sleeps 3–6 3 Bedrooms 🐾 2 Dogs 🎉 Celebrations
Next Available 21/03 to 03/04/2026
Facilities
WiFi Microwave Dishwasher Washing machine Garden BBQ Parking
Type of Holiday
2 dogs welcome Special celebrations
Stanton House, Gloucestershire, England
Viewed 10× this week

Stanton House

Stow-on-the-Wold, Gloucestershire ~14 miles from Cheltenham
Sleeps 8–14 6 Bedrooms 🐾 2 Dogs
Next Available 16/04 to 24/04/2026
Facilities
WiFi Microwave Dishwasher Washing machine Games room Tennis Garden BBQ
Type of Holiday
2 dogs welcome Group welcome Weddings Corporate events
The Clock Tower, Herefordshire, England
Viewed 5× this week No booking fee

The Clock Tower

Colwall, Herefordshire ~17 miles from Cheltenham
Sleeps 1–2 1 Bedroom 🐾 2 Dogs 🎉 Celebrations
Next Available 22/03 to 03/04/2026
Facilities
WiFi Woodburner Coffee machine Microwave Dishwasher Garden BBQ EV Charging
Type of Holiday
2 dogs welcome Special celebrations Weddings
Broadway House, Gloucestershire, England
Viewed 12× this week

Broadway House

Stow-on-the-Wold, Gloucestershire ~15 miles from Cheltenham
Sleeps 7–16 7 Bedrooms 🐾 2 Dogs 🎉 Celebrations
Next Available 22/03 to 27/03/2026
Facilities
WiFi Microwave Dishwasher Washing machine Games room Tennis Garden BBQ
Type of Holiday
2 dogs welcome Special celebrations Hen Parties Group welcome Weddings
8 Bedroom Stanway House, Gloucestershire, England
Viewed 13× this week

8 Bedroom Stanway House

Stow-on-the-Wold, Gloucestershire ~14 miles from Cheltenham
Sleeps 8–18 8 Bedrooms 🚫 No Dogs 🎉 Celebrations
Next Available 10/04 to 15/04/2026
Facilities
WiFi Microwave Dishwasher Washing machine Games room Tennis Garden BBQ
Type of Holiday
No dogs allowed Special celebrations Group welcome Weddings Corporate events
Barton Court, Herefordshire, England
Viewed 9× this week No booking fee

Barton Court

Colwall, Herefordshire ~17 miles from Cheltenham
Sleeps 11–27 11 Bedrooms 🐾 4 Dogs 🎉 Celebrations
Next Available 22/03 to 27/03/2026
Facilities
WiFi Coffee machine Microwave Dishwasher Garden Firepit BBQ EV Charging
Type of Holiday
4 dogs welcome Special celebrations Hen Parties Stag parties Group welcome


Cottages, Apartments & Lodges in Cheltenham, Gloucestershire, England

RuralHomeStays.Com features holiday home(s) within or close to Cheltenham, enjoy browsing through the available options. We hope you find the perfect holiday house for you in Cheltenham, Gloucestershire.


Self-Catering Breaks in Cheltenham

Discover some of the best of Cheltenham on a self-catering break. Whether you opt to rent an apartment or a town house in this stylish spa town, or stay in a cottage in the nearby countryside, Cheltenham has plenty to offer visitors.

What Does Cheltenham Offer for Cottage Breaks?

Cheltenham is undoubtedly one of the Cotswolds’ most cosmopolitan and stylish towns. The spa town’s reputation was greatly enhanced when George III and Queen Charlotte took the waters in 1788. It is abundant in history and architecture—Cheltenham Ladies College founded in 1841 is now predominantly a mixture of Victorian Decorated Gothic and late 20th-century work and is definitely worth a visit.

Attractions to Discover in and near Cheltenham on a Cottage Break

No visit to Cheltenham is complete without spending some time browsing the Montpellier area. The Montpellier Gardens were opened in 1809 to cover the most lavish building of Montpellier Spa and host a variety of activities throughout the summer including live music. Shopping in Montpellier is a must; there are numerous specialist shops and boutiques, all amidst a host of bars, cafes, pubs, and restaurants.

Events and Festivals in Cheltenham

The inaugural classic steeplechase of the season, the Gold Cup, was first held at Cheltenham in 1924. The Cheltenham Gold Cup Steeplechase is now a fixture of the Cheltenham Festival in March, a time when countless thousands of visitors hit Cheltenham en masse.

Places to Visit in Cheltenham

- Cheltenham Race Course - Prestbury Park, Cheltenham - The Holst Birthplace Museum - The Cheltenham Art Gallery and Museum Whether you're planning for a hen party, a family holiday, or a romantic break, we hope you find the perfect accommodation for your Cheltenham holiday on Ruralhomestays.com.

Updated