Book Holiday Homes in Cheltenham

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Cheltenham

17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water

17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water

Clapton-on-the-Hill
With a stay at this vacation home in Cheltenham, you'll be within a 10-minute drive of Cotswold Motoring Museum and Bourton Model Railway Exhibition.
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water
elegant period 5 bed house close to town centre,sleeps 15

elegant period 5 bed house close to town centre,sleeps 15

Cheltenham
The price is AU$1,234 per night from 6 Jan to 7 Jan
AU$1,234
includes taxes & fees
6 Jan - 7 Jan 2025
With a stay at this vacation home in Cheltenham, you'll be within a 5-minute drive of Cheltenham Racecourse and Cheltenham Playhouse.
elegant period 5 bed house close to town centre,sleeps 15
Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe.

Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe.

Winchcombe
Located in Cheltenham, this vacation home is in a rural location, within a 15-minute walk of Winchcombe Folk and Police Museum and Belas Knap.
Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe.
Save an average of 15% on thousands of hotels when you're signed in
A Luxurious family Cotswold home with a short stroll from market-square

A Luxurious family Cotswold home with a short stroll from market-square

Stow-on-the-Wold
Located in Cheltenham, this vacation home is in a rural location, within a 15-minute walk of Fosse Gallery Fine Art and St. Edward's Church.
A Luxurious family Cotswold home with a short stroll from market-square
Luxurious Georgian Townhouse in Cheltenham Centre

Luxurious Georgian Townhouse in Cheltenham Centre

Cheltenham
With a stay at this vacation home, you'll be centrally located in Cheltenham, within a 5-minute drive of Cheltenham Racecourse and Holst Birthplace Museum.
Luxurious Georgian Townhouse in Cheltenham Centre
Sleeps 14, 7 Bedrooms, 2 Dogs Welcome, No Smoking, Wood burner, Garden, Cot and Highchair,  Children

Sleeps 14, 7 Bedrooms, 2 Dogs Welcome, No Smoking, Wood burner, Garden, Cot and Highchair, Children

Cheltenham
When you stay at this vacation home in Cheltenham, you'll be within a 10-minute drive of Bourton Model Railway Exhibition and Cotswold Motoring Museum.
Sleeps 14, 7 Bedrooms, 2 Dogs Welcome, No Smoking, Wood burner, Garden, Cot and Highchair, Children
Elliot Oliver - 2 The Old Surgery: Stunning 4 Bedroom Home With Parking In Cheltenham

Elliot Oliver - 2 The Old Surgery: Stunning 4 Bedroom Home With Parking In Cheltenham

4 out of 5
2 The Old Surgery, Prestbury Road, Cheltenham, England
With a stay at this vacation home in Cheltenham, you'll be within a 5-minute drive of Cheltenham Racecourse and The Promenade.
Elliot Oliver - 2 The Old Surgery: Stunning 4 Bedroom Home With Parking In Cheltenham
The Old Antique Shop Town Centre Stylish House

The Old Antique Shop Town Centre Stylish House

Stow-on-the-Wold
Located in Cheltenham, this vacation home is in a rural location, within a 15-minute walk of St. Edward's Church and Fosse Gallery Fine Art.
The Old Antique Shop Town Centre Stylish House
Beautiful Cheltenham Townhouse, Private Parking

Beautiful Cheltenham Townhouse, Private Parking

Gloucestershire
With a stay at this vacation home in Cheltenham, you'll be within a 10-minute drive of Cheltenham Racecourse and University of Gloucestershire.
Beautiful Cheltenham Townhouse, Private Parking
Don't see what you're looking for?
See all available properties in Cheltenham
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cheltenham Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Cheltenham vacation homes are the perfect way for you to wing it.

Holiday houses in Cheltenham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Cheltenham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Cheltenham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Cheltenham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Cheltenham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Cheltenham Holiday Homes essential information

Accommodation
207 Holiday Homes
Lowest Price
AU$136
Highest Price
AU$1,234
Popular accommodation
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water, elegant period 5 bed house close to town centre,sleeps 15, Stunning Grade II listed cottage on Vineyard Street in the heart of Winchcombe. , A Luxurious family Cotswold home with a short stroll from market-square , Luxurious Georgian Townhouse in Cheltenham Centre, Sleeps 14, 7 Bedrooms, 2 Dogs Welcome, No Smoking, Wood burner, Garden, Cot and Highchair, Children, Elliot Oliver - 2 The Old Surgery: Stunning 4 Bedroom Home With Parking In Cheltenham, The Old Antique Shop Town Centre Stylish House, Beautiful Cheltenham Townhouse, Private Parking

Top trending hotels in Cheltenham

Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 29 Dec to 30 Dec
AU$143
includes taxes & fees
29 Dec - 30 Dec
With a stay at Leonardo Hotel Cheltenham, you'll be centrally located in Cheltenham, within a 10-minute drive of Cheltenham Racecourse and Imperial Gardens.
Leonardo Hotel Cheltenham
The Frogmill

The Frogmill

3.5 out of 5
A436, Shipton Oliffe, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 5 Jan to 6 Jan
AU$211
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at The Frogmill in Cheltenham, you'll be within a 15-minute drive of Cheltenham Racecourse and Whittington Court.
The Frogmill
The George

The George

3.5 out of 5
Saint George's Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is AU$136 per night from 5 Jan to 6 Jan
AU$136
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at The George in Cheltenham, you'll be within a 5-minute drive of Cheltenham Racecourse and Imperial Gardens.
The George
Save an average of 15% on thousands of hotels when you're signed in
Queens Hotel Cheltenham

Queens Hotel Cheltenham

4 out of 5
The Promenade, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 5 Jan to 6 Jan
AU$163
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Queens Hotel Cheltenham, you'll be centrally located in Cheltenham, within a 5-minute drive of Cheltenham Racecourse and Imperial Gardens.
Queens Hotel Cheltenham
Don't see what you're looking for?
See all available properties in Cheltenham
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.