Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Dover
The price is NZ$2,025 per night from 23 Feb to 24 Feb
NZ$2,025
includes taxes & fees
23 Feb - 24 Feb
Stay at this vacation home in West Dover. Enjoy free WiFi, a fitness center, and patios. Popular attractions Mount Snow and Snow Lake are located nearby.
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Stratton
Book a stay at this family-friendly vacation home in Winhall. Enjoy free WiFi, a garden, and patios. Popular attractions Stratton Mountain Resort and Stratton ...
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle
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
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Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Dover
Book a stay at this golf vacation home in West Dover. Enjoy free WiFi, a fitness center, and patios. Popular attractions Mount Snow and Snow Lake are located ...
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski
Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Dover
Book a stay at this ski vacation home in West Dover. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Mount Snow and Nitro Express Ski Lift ...
Ski-In condo at Mount Snow with Fireplace, Bears Crossing
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.
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
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow
The price is NZ$737 per night from 28 Jan to 29 Jan
NZ$737
includes taxes & fees
28 Jan - 29 Jan
Stay at this vacation home in Ludlow. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Okemo Mountain Resort and Dorsey Park are ...
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Historic 6-BR Across From Equinox Resort

Historic 6-BR Across From Equinox Resort

Manchester
Stay at this vacation home in Manchester. Enjoy in-room fireplaces. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located ...
Historic 6-BR Across From Equinox Resort
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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
890 Holiday Homes
Lowest Price
NZ$265
Highest Price
NZ$2,025
Popular accommodation
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!, Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski, Ski-In condo at Mount Snow with Fireplace, Bears Crossing, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle, Historic 6-BR Across From Equinox Resort

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$265 per night from 28 Jan to 29 Jan
NZ$265
includes taxes & fees
28 Jan - 29 Jan
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
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11, Chester, VT
Fully refundableReserve now, pay when you stay
Stay at this 3-star B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Stone Hearth Inn and Eatery
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$672 per night from 23 Feb to 24 Feb
NZ$672
includes taxes & fees
23 Feb - 24 Feb
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
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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
The price is NZ$368 per night from 2 Feb to 3 Feb
NZ$368
includes taxes & fees
2 Feb - 3 Feb
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our ...
The Equinox Golf Resort & Spa
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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.