Book Holiday Homes in Cheltenham

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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
Stay at this vacation home in Cheltenham. Enjoy free WiFi, a garden, and patios. Popular attractions Dragonfly Maze and Birdland Park and Gardens are located ...
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water
The Little House, Luxury Cotswolds Stunning Views

The Little House, Luxury Cotswolds Stunning Views

Cheltenham
Stay at this vacation home in Cheltenham. Enjoy free WiFi, a garden, and patios. Popular attractions Cerney House Gardens and Crickley Hill Country Park are ...
The Little House, Luxury Cotswolds Stunning Views
K Suites - Spacious 2- Bedroom House w/ free Wi-Fi and parkiing

K Suites - Spacious 2- Bedroom House w/ free Wi-Fi and parkiing

Cheltenham
Stay at this vacation home in Cheltenham. Enjoy a garden and housekeeping. Popular attractions Cheltenham Racecourse and Holst Birthplace Museum are located ...
K Suites - Spacious 2- Bedroom House w/ free Wi-Fi and parkiing
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Gloucester Place Townhouse + Hot Tub!

Gloucester Place Townhouse + Hot Tub!

Cheltenham
Stay at this vacation home in Cheltenham. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Cheltenham Racecourse and Everyman Theatre ...
Gloucester Place Townhouse + Hot Tub!
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
Stay at this 4-star vacation home in Cheltenham. Enjoy free WiFi, free parking, and a garden. Popular attractions Cheltenham Racecourse and Statue of Edward ...
Elliot Oliver - 2 The Old Surgery: Stunning 4 Bedroom Home With Parking In Cheltenham
Beautiful Cheltenham Townhouse, Private Parking

Beautiful Cheltenham Townhouse, Private Parking

Gloucestershire
Stay at this vacation home in Cheltenham. Enjoy an in-room coffeemaker and in-room fireplaces. Popular attractions Cheltenham Racecourse and Imperial Gardens ...
Beautiful Cheltenham Townhouse, Private Parking
Old Sorting Office

Old Sorting Office

3 out of 5
Cheltenham
Stay at this 3-star cottage in Cheltenham. Enjoy free WiFi, free parking, and a garden. Popular attractions Cheltenham Racecourse and Winchcombe Folk and Police ...
Old Sorting Office
Luxury Cotswolds Cottage with Hot Tub, Luxury Boutique Cotswold Cottage with Hot Tub!

Luxury Cotswolds Cottage with Hot Tub, Luxury Boutique Cotswold Cottage with Hot Tub!

Winchcombe
Book a stay at this family-friendly vacation home in Cheltenham. Enjoy a garden, an in-room coffeemaker, and in-room fireplaces. Popular attractions Cheltenham ...
Luxury Cotswolds Cottage with Hot Tub, Luxury Boutique Cotswold Cottage with Hot Tub!
Central 1 BD in the Heart of Cheltenham

Central 1 BD in the Heart of Cheltenham

2 out of 5
Warwick Pl, Cheltenham, England
Stay at this vacation home in Cheltenham. Enjoy free WiFi and free parking. Popular attractions Cheltenham Racecourse and Holst Birthplace Museum are located ...
Central 1 BD in the Heart of Cheltenham
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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
211 Holiday Homes
Lowest Price
NZ$150
Highest Price
NZ$228
Popular accommodation
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water, The Little House, Luxury Cotswolds Stunning Views, K Suites - Spacious 2- Bedroom House w/ free Wi-Fi and parkiing, Gloucester Place Townhouse + Hot Tub!, Elliot Oliver - 2 The Old Surgery: Stunning 4 Bedroom Home With Parking In Cheltenham, Beautiful Cheltenham Townhouse, Private Parking, Old Sorting Office, Luxury Cotswolds Cottage with Hot Tub, Luxury Boutique Cotswold Cottage with Hot Tub!, Central 1 BD in the Heart of Cheltenham

Top trending hotels in Cheltenham

Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
The price is NZ$150 per night from 10 Nov to 11 Nov
NZ$150
includes taxes & fees
10 Nov - 11 Nov
Book a stay at this eco-certified hotel in Cheltenham. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful ...
Leonardo Hotel Cheltenham
Delta Hotels by Marriott Cheltenham Chase

Delta Hotels by Marriott Cheltenham Chase

4 out of 5
Shurdington Road, Brockworth, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is NZ$169 per night from 1 Dec to 2 Dec
NZ$169
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this spa hotel in Cheltenham. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in ...
Delta Hotels by Marriott Cheltenham Chase
The Frogmill

The Frogmill

3.5 out of 5
A436, Shipton Oliffe, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is NZ$228 per night from 17 Nov to 18 Nov
NZ$228
includes taxes & fees
17 Nov - 18 Nov
Stay at this 3.5-star hotel in Cheltenham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
The Frogmill
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Queens Hotel Cheltenham

Queens Hotel Cheltenham

4 out of 5
The Promenade, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 24 Nov to 25 Nov
NZ$195
includes taxes & fees
24 Nov - 25 Nov
Stay at this 4-star eco-certified hotel in Cheltenham. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Queens Hotel Cheltenham
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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.

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^Subject to availability and chosen travel dates.