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Book a cottage break in Cheltenham, Gloucestershire, England

Showing all properties across the UK. Select a destination from the list to refine your search.
27 holiday rentals
Family-Friendly
Viewed 43 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 welcome
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.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
smart TVdishwasher in kitchenmicrowave in kitchengames roomtennis courtfree Wifienclosed gardenBBQParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £1390
Next available: 02 Jan - 7 nights
Online Booking Available
Viewed 29 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)
countryside views over fields and farmlands near local pub
Facilities, Features & Awards:
smart TVmicrowave in kitchengames roomindoor heated poolfree Wifienclosed gardenBBQParking
Sorry, this owner/agency has not provided availability information.
7 nights from £425
book online online booking
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Family-Friendly
Viewed 38 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 welcome
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.

ensuite bedroom(s) near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchengames roomtennis courtfree WifigardenParking
This owner/agency is showing availability but has not provided full pricing information.
7 nights from £1590
Next available: 15 Dec - 7 nights
Romantic Retreat
Viewed 22 times recently.
Cheltenham 18 miles away

The Shepherds Hut,

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

Charming shepherd’s hut in Worcestershire countryside, near Worcester and Malvern Hills.

ground floor bedroomensuite bedroom(s)
Facilities, Features & Awards:
microwave in kitchenBBQParkinggarden
Sorry, this owner/agency has not provided availability and full price information.
7 nights from £540
Online Booking Available
Viewed 20 times recently.
Cheltenham 13 miles away

Pennylands Hill View Lodge,

Broadway, Worcestershire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
 dog-friendly cottage

Nestled in Worcestershire's picturesque countryside near Broadway, Pennylands Hill View Lodge offers breathtaking views, sleeps 4, features a cosy woodburner-effect fire, and is ideally located for exploring the Cotswolds; sorry, no pets.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenfree WifigardenParking
7 nights from £512
Next available: 14 Dec - 7 nights
book online online booking
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Cheltenham 13 miles away

Greyhound Barn,

Cirencester, Gloucestershire, England
sleeps  17 sleeps 17
8 bedrooms 8 bedrooms
9 bathrooms 9 bathrooms
 dog-friendly cottage
family friendly family friendly

Greyhound Farm House in Barnsley, Gloucestershire, offers a historical retreat in the Cotswold countryside, sleeping up to 16 guests, with garden and BBQ, close to Cheltenham's attractions; sorry, no pets allowed.

ground floor bedroom near local pub
Facilities, Features & Awards:
dishwasher in kitchenfree Wifigarden
7 nights from £1987
Next available: 15 Dec - 3 nights
book online online booking
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Online Booking Available
Viewed 41 times recently.
Cheltenham 14 miles away

Parlour Rural Retreat near the Malvern Hills and Cotswolds,

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

Good quality 1 bedroom barn conversion with views of the Worcestershire countryside, set on a working farm, this is an ideal place for two people looking to enjoy a rural retreat break conveniently close to the Cotswolds, the super-king size bedroom, warming wood burner and access to an outdoor hot tub help to make this a special place for a relaxing romantic couple's holiday.

Facilities, Features & Awards:
TVdishwasher in kitchenoutdoor hot tub accessfree Wifigardenwood burning stoveParking
7 nights from £512
Next available: 08 Dec - 5 nights
book online online booking
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Online Booking Available
Viewed 18 times recently.
Cheltenham 18 miles away

The Escape Romantic Retreat,

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

Romantic retreat in Malvern close to the Malvern Hills Area of Outstanding Natural Beauty.

ground floor bedroom near local pub
Facilities, Features & Awards:
smart TVmicrowave in kitchenfree WifigardenParking
7 nights from £432
Next available: 07 Dec - 6 nights
book online online booking
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Online Booking Available
Viewed 31 times recently.
Cheltenham 9 miles away

Secret Island Yurt,

Tewkesbury, Gloucestershire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
2 bathrooms 2 bathrooms
no dogs allowed No pets

Discover a romantic lakeside retreat at Secret Island Yurt in Worcestershire, nestled in the Cotswolds with serene lake views, a private hot tub, sauna, and rowing boat, sleeping 2 guests — sorry, no pets.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchensaunaParking
7 nights from £577
Next available: 10 Apr - 7 nights
book online online booking
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Online Booking Available
Viewed 41 times recently.
Cheltenham 9 miles away

Lakeside Yurt, Cotswolds,

Beckford, Worcestershire, England
sleeps  2 sleeps 2
1 bedrooms 1 bedroom
1 bathrooms 1 bathroom
 1 dog welcome  1 dog allowed

Stylish and generously sized holiday yurt featuring a romantic bed, a high quality kitchen area, private hot tub and an excellent location right by a lake and sleeping 2, this unique holiday home was made for romantic glamping getaways.

lake views
Facilities, Features & Awards:
TVdishwasher in kitchenmicrowave in kitchenoutdoor hot tub accesssaunaParking
7 nights from £452
book online online booking
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Cheltenham 19 miles away

The Olde House,

Ross-on-Wye, Herefordshire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
1 bathrooms 1 bathroom
 dog-friendly cottage
family friendly family friendly

Nestled in the picturesque village of Upton Bishop, Herefordshire, this charming semi-detached cottage offers distant views of the Malvern Hills, sleeps six, and boasts a cosy open fire, but sorry no pets.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVmicrowave in kitchenfree WifigardenfireplaceBBQParking
7 nights from £377
Next available: 14 Mar - 7 nights
book online online booking
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Online Booking Available
Viewed 26 times recently.
Cheltenham 13 miles away

Pennylands Willow Lodge,

Evesham, Worcestershire, England
sleeps  4 sleeps 4
2 bedrooms 2 bedrooms
2 bathrooms 2 bathrooms
 dog-friendly cottage
family friendly family friendly

Pennylands Willow Lodge: A charming, dog-friendly retreat in Worcestershire's Cotswolds, offering stunning countryside views, sleeps 4, and features an open-plan living area with a garden and BBQ, just a short walk from Broadway village.

ground floor bedroom near local pub
Facilities, Features & Awards:
TVdishwasher in kitchenfree WifigardenParking
7 nights from £570
Next available: 07 Dec - 4 nights
book online online booking
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* 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.

Cheltenham Holiday Rental Searches