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
When you a stay at this vacation home in Manchester Center, you'll be next to a golf course, within a 5-minute walk of Green Mountain National Forest and Battenkill ...
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 AU$947 per night from 17 Apr to 18 Apr
AU$947
includes taxes & fees
17 Apr - 18 Apr
Located in Keene, this vacation home is within a 15-minute walk of Ashuelot River and Cheshire Children's Museum.
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
With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.
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
When you stay at this vacation home in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National ...
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
With a stay at this vacation home in Rupert, you'll be on a river, just steps from Green Mountain National Forest and a 4-minute drive from Dorset Historical ...
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
Located in Jamaica, this vacation home is within a 5-minute drive of West River and Green Mountain National Forest.
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
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 5-minute drive of Okemo Mountain Resort and Red Lot.
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
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 5-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
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
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
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
AU$222
Highest Price
AU$947
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 AU$222 per night from 4 May to 5 May
AU$222
includes taxes & fees
4 May - 5 May
Located in Chester (Chester Depot), Fullerton Inn is within a 15-minute drive of Vermont Country Store and Springfield Hospital.
Fullerton Inn
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 AU$229 per night from 6 Apr to 7 Apr
AU$229
includes taxes & fees
6 Apr - 7 Apr
Located in Brownsville, Holiday Inn Club Vacations Mount Ascutney Resort by IHG is in a national park, within a 15-minute drive of American Precision Museum ...
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$590 per night from 6 Apr to 7 Apr
AU$590
includes taxes & fees
6 Apr - 7 Apr
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
Woodstock Inn & Resort
Save an average of 15% on thousands of hotels when you're signed in
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 AU$279 per night from 8 Apr to 9 Apr
AU$279
includes taxes & fees
8 Apr - 9 Apr
When you a stay at The Equinox Golf Resort & Spa in Manchester, you'll be in the mountains, just steps from Green Mountain National Forest and Golf Club at ...
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.