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 AU$573 per night from 24 Mar to 25 Mar
AU$573
includes taxes & fees
24 Mar - 25 Mar
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
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
With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National ...
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle
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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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
Ski-In condo at Mount Snow with Fireplace, Bears Crossing

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

Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Ski-In condo at Mount Snow with Fireplace, Bears Crossing
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
With a stay at this vacation home in West Dover, you'll be next to a golf course, within a 5-minute drive of Mount Snow and North Branch Deerfield River.
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski
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 5-minute drive of Killington Resort and Skyeship Express Gondola Stage I.
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
The price is AU$1,546 per night from 5 Mar to 6 Mar
AU$1,546
includes taxes & fees
5 Mar - 6 Mar
Located in Winhall, this vacation home is in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Bromley Mountain Ski ...
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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 AU$670 per night from 1 Apr to 2 Apr
AU$670
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute drive of Okemo Mountain Resort and Dorsey Park.
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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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
910 Holiday Homes
Lowest Price
AU$193
Highest Price
AU$1,546
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, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Ski-In condo at Mount Snow with Fireplace, Bears Crossing, Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Your Vermont Mountain Haven Pet Friendly home with Hot tub!, Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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$226 per night from 11 Mar to 12 Mar
AU$226
includes taxes & fees
11 Mar - 12 Mar
With a stay at Fullerton Inn in Chester (Chester Depot), you'll be steps from DaVallia Art & Accents and a 4-minute drive from Bonnie's Bundles Dolls.
Fullerton Inn
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester
When you stay at this cabin in Chester, you'll be 15 minutes by car from Fletcher Farm School for the Arts and Crafts.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$600 per night from 23 Mar to 24 Mar
AU$600
includes taxes & fees
23 Mar - 24 Mar
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
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Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 6 Mar to 7 Mar
AU$193
includes taxes & fees
6 Mar - 7 Mar
A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus ...
Colonial Motel And Spa
Don't see what you're looking for?
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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.