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
Rural hideaway but only 5 minutes from the centre of Cheltenham

Rural hideaway but only 5 minutes from the centre of Cheltenham

Cheltenham, Glos.
Stay at this vacation home in Cheltenham. Enjoy free WiFi and a garden. Popular attractions Cheltenham Racecourse and Jonny-Rocks Stadium are located ...
Rural hideaway but only 5 minutes from the centre of Cheltenham
Honeypot Cottage-Lovely Bolthole in Stow

Honeypot Cottage-Lovely Bolthole in Stow

2 out of 5
36 Well Ln, Cheltenham, England
Stay at this vacation home in Cheltenham. Enjoy free WiFi and free parking. Popular attractions St. Edward's Church and Fosse Gallery Fine Art are located ...
Honeypot Cottage-Lovely Bolthole in Stow
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NEW LISTING - Chic Apt in Central Cheltenham Free Permit Parking

NEW LISTING - Chic Apt in Central Cheltenham Free Permit Parking

Cheltenham
Book a stay at this family-friendly vacation home in Cheltenham. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Cheltenham ...
NEW LISTING - Chic Apt in Central Cheltenham Free Permit Parking
Spacious 5-Bedroom Home in Cheltenham

Spacious 5-Bedroom Home in Cheltenham

Cheltenham
Enjoy a garden and a pool table. Popular attractions Cheltenham Racecourse and Imperial Gardens are located nearby.
Spacious 5-Bedroom Home in Cheltenham
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
A quiet Edwardian house in the Cotswolds

A quiet Edwardian house in the Cotswolds

Stroud
Book a stay at this family-friendly vacation home in Stroud. Enjoy free breakfast, free WiFi, and a water park. Popular attractions Gloucester Quays and St Mary’s ...
A quiet Edwardian house in the Cotswolds
The Old Antique Shop Town Centre Stylish House

The Old Antique Shop Town Centre Stylish House

Stow-on-the-Wold
Stay at this vacation home in Cheltenham. Enjoy free WiFi. Popular attractions St. Edward's Church and Fosse Gallery Fine Art are located nearby.
The Old Antique Shop Town Centre Stylish House
Suitely Upper Park Place

Suitely Upper Park Place

Cheltenham
Stay at this vacation home in Cheltenham. Enjoy in-room washers/dryers. Popular attractions Cheltenham Racecourse and Cheltenham Art Gallery and Museum are located ...
Suitely Upper Park Place
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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
255 Holiday Homes
Lowest Price
NZ$161
Highest Price
NZ$233
Popular accommodation
17th century converted barn in Cotswolds stone- 5 mins from Bourton On The Water, Rural hideaway but only 5 minutes from the centre of Cheltenham, Honeypot Cottage-Lovely Bolthole in Stow, NEW LISTING - Chic Apt in Central Cheltenham Free Permit Parking, Spacious 5-Bedroom Home in Cheltenham, The Little House, Luxury Cotswolds Stunning Views, A quiet Edwardian house in the Cotswolds , The Old Antique Shop Town Centre Stylish House, Suitely Upper Park Place

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 NZ$161 per night from 13 Apr to 14 Apr
NZ$161
includes taxes & fees
13 Apr - 14 Apr
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
DoubleTree by Hilton Cheltenham-Cotswolds

DoubleTree by Hilton Cheltenham-Cotswolds

4 out of 5
Cirencester Road, Charlton Kings, Cheltenham, England
The price is NZ$166 per night from 27 Apr to 28 Apr
NZ$166
includes taxes & fees
27 Apr - 28 Apr
Stay at this 4-star spa hotel in Cheltenham. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Cheltenham-Cotswolds
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 NZ$233 per night from 6 Apr to 7 Apr
NZ$233
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3.5-star hotel in Cheltenham. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful ...
The George
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Holiday Inn Express Cheltenham by IHG

Holiday Inn Express Cheltenham by IHG

3 out of 5
Dunalley Street, Cheltenham, England
Fully refundable
The price is NZ$182 per night from 6 Apr to 7 Apr
NZ$182
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star eco-certified hotel in Cheltenham. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our ...
Holiday Inn Express Cheltenham by IHG
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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.

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