Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
Book a stay at this golf vacation home in Manchester Center. Enjoy a water park, a garden, and a pool table. Popular attractions Dana L. Thompson Memorial Park ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Cozy Home Near Downtown, Shops, and Restaurants.

Cozy Home Near Downtown, Shops, and Restaurants.

2 out of 5
Keene
The price is NZ$1,019 per night from 7 Apr to 8 Apr
NZ$1,019
includes taxes & fees
7 Apr - 8 Apr
Stay at this vacation home in Keene. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Ashuelot River and Cheshire Children's Museum are ...
Cozy Home Near Downtown, Shops, and Restaurants.
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Killington
Stay at this vacation home in Killington. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Killington Resort and Pico Mountain ...
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
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Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
Book a stay at this ski vacation home in Stratton. Enjoy a garden, ski-in/ski-out access, and patios. Popular attractions Stratton Mountain Resort and Stratton ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset
Stay at this vacation home in Rupert. Enjoy free WiFi, a garden, and patios. Popular attractions Dorset Historical Society Museum and Dorset Playhouse are located ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Stay at this vacation home in Jamaica. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Hot Glass Works and Ball Mountain State ...
Potter's Place | House in Jamaica with mountain views
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
Stay at this vacation home in Ludlow. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Okemo Mountain Resort and Sachem ...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Ludlow
Stay at this vacation home in Ludlow. Enjoy free WiFi, a garden, and patios. Popular attractions Okemo Mountain Resort and Green Mountain Sugar House are located ...
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Mount Snow and Heavy Metal Ski ...
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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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.

Chester 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 Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester 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 Chester 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 Chester adventures, obvs.

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

Chester Holiday Homes essential information

Accommodation
1086 Holiday Homes
Lowest Price
NZ$243
Highest Price
NZ$1,019
Popular accommodation
Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Cozy Home Near Downtown, Shops, and Restaurants., Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Potter's Place | House in Jamaica with mountain views, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Top trending hotels in Chester

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
The price is NZ$243 per night from 5 Apr to 6 Apr
NZ$243
includes taxes & fees
5 Apr - 6 Apr
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$644 per night from 6 Apr to 7 Apr
NZ$644
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road, Brownsville, VT
Fully refundable
The price is NZ$247 per night from 6 Apr to 7 Apr
NZ$247
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our ...
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 8 Apr to 9 Apr
NZ$304
includes taxes & fees
8 Apr - 9 Apr
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
The Equinox Golf Resort & Spa
Don't see what you're looking for?
See all available properties in Chester
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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.