Book a cottage break in Cheltenham, Gloucestershire, England

22 holiday rentals
Family-Friendly
Viewed 26 times recently.
Cheltenham 18 miles away

The Barn,

Worcester, Worcestershire, England
sleeps  6 sleeps 6
3 bedrooms 3 bedrooms
2 bathrooms 2 bathrooms
 dog-friendly cottage
family friendly family friendly

Wonderful rural barn conversion with fantastic views out to the Malvern Hills, situated within its own private fenced garden on a small holding and surrounded by glorious Worcestershire countryside, both family-friendly and dog-friendly.

0 ( reviews)
ensuite(s)
Facilities, Features & Awards:
TVDishwasherWashing machineMicrowaveTennis courtParkingEnclosed Garden
7 nights from £330
Next available: 27 Apr - 6 nights
Online Booking Available
Viewed 46 times recently.
Cheltenham 20 miles away

Stable Cottage,

Stratford-upon-Avon, Warwickshire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
no dogs allowed No pets
family friendly family friendly

2 bedroom rural retreat with country views, private indoor pool access, games room and private courtyard, set on a working farm just 5 miles from the English Cotswolds and 8 miles from Stratford upon Avon.

5 (1 reviews)
country views
Facilities, Features & Awards:
Digital TVWashing machineMicrowaveGames roomHeated poolParkingEnclosed Garden
Sorry, this owner/agency has not provided availability information.
7 nights from £425
book online online booking
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Cheltenham 15 miles away

Bankside Cottage,

Blockley, Gloucestershire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
2 bathrooms 2 bathrooms
no dogs allowed No pets
family friendly family friendly

Charming 2 bedroom stone-built cottage in the Cotswolds with lovely country views and courtyard, sorry no pets.

0 ( reviews)
Facilities, Features & Awards:
TVDishwasherMicrowaveFree WifiGardenParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £787
book online online booking
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Family-Friendly
Viewed 34 times recently.
Cheltenham 13 miles away

Broadway House,

Stow-on-the-Wold, Gloucestershire, England
sleeps  16 sleeps 16
7 bedrooms 7 bedrooms
6 bathrooms 6 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

Fantastic large self-catering house which is both family-friendly and dog-friendly, offering a high standard of accommodation as well as countryside views in a rural location just 2 miles from Stow on the Wold in the Cotswolds.

0 ( reviews)
ground floor bedroomensuite(s)
Facilities, Features & Awards:
Digital TVDishwasherWashing machineMicrowaveGames roomTennis courtFree WifiEnclosed GardenParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £1390
Next available: 20 Jun - 7 nights
Family-Friendly
Viewed 20 times recently.
Cheltenham 14 miles away

Stanway House,

Stow-on-the-Wold, Gloucestershire, England
sleeps  18 sleeps 18
8 bedrooms 8 bedrooms
6 bathrooms 6 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

Lovely large stone-built holiday cottage with 8 bedrooms, 6 bathrooms and country views, ideal for large groups of friends or family, with a lovely rural location only 2 miles from Stow-on-the-Wold in the Cotswolds.

0 ( reviews)
ensuite(s)
Facilities, Features & Awards:
TVDishwasherMicrowaveGames roomTennis courtFree WifiGardenParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £1590
Next available: 20 Jun - 7 nights
Romantic Retreat
Viewed 10 times recently.
Cheltenham 16 miles away

Rhydd Holiday Barn,

Malvern, Worcestershire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
2 bathrooms 2 bathrooms
no dogs allowed No pets

4 star Gold Award winning barn conversion near Malvern with stunning views out to the Malvern Hills.

0 ( reviews)
ensuite(s)country views
Facilities, Features & Awards:
Gold Award Winning CottageDigital TVDishwasherWashing machineMicrowaveFree WifiGardenParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £430
Next available: 24 May - 7 nights
Family-Friendly
Viewed 34 times recently.
Cheltenham 14 miles away

Stanton House,

Stow-on-the-Wold, Gloucestershire, England
sleeps  14 sleeps 14
6 bedrooms 6 bedrooms
5 bathrooms 5 bathrooms
2 dogs welcome  2 dogs
family friendly family friendly

Perfect for large groups or families looking to explore the beautiful Cotswolds, this stone-built holiday cottage is part of the Flagstone Farm development and has 6 bedrooms and 5 bathrooms as well as lovely views of the surrounding countryside.

0 ( reviews)
ensuite(s)
Facilities, Features & Awards:
TVDishwasherWashing machineMicrowaveGames roomTennis courtFree WifiEnclosed GardenParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £1290
Next available: 02 Jun - 7 nights
* Price quoted is not inclusive of any applicable booking fees or local charges.
Cheltenham is a stylish place for a self-catering break.  With its grand historical buildings and strong reputation as a spa town, Cheltenham has to be one of the Cotswold’s most stylish towns.  With a huge choice of shops, restaurants and bars, Cheltenham in many ways has quite a city feel. The spa town’s wealth of history and impressive architecture with grand Victorian buildings mean that Cheltenham is a great place to take a cottage break.  

What Cheltenham, Gloucestershire offers for Self-Catering Holidays


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.

Cheltenham is also known for its race course and has art galleries as well as museums to interest visitors.   Cheltenham is well based for exploring the Cotswolds which are within easy reach.  Whether you opt to rent a self-catering apartment in Cheltenham or a cottage in the country, we trust that you will have a great time exploring Cheltenham.

Whether you choose to book a holiday cottage in Cheltenham, an apartment, a lodge or another type of self-catering holiday accommodation, we hope you have your best holiday yet in Gloucestershire.

Frequently Asked Questions about Cheltenham

The best places to stay depend on your preferences, interests and the type of accommodation that best suits you. Country Cottages Online features a great selection of good quality rentals.
See our selection of pet-friendly rentals in Cheltenham, or use the filters to refine your search.
See our selection of lodges and cabins in Cheltenham, Gloucestershire.
Read the description of Cheltenham to find out ideas and tips on the best things to see and do. Also see our area guides for more information on what Gloucestershire has to offer for holidaymakers.