Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

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.
Opens in a new windowClassic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Idyllic Lakefront House Suited Two  Families

Idyllic Lakefront House Suited Two Families

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 10-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Opens in a new windowIdyllic Lakefront House Suited Two Families
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Ludlow
With a stay at this vacation home in Ludlow, you'll be on a lake, within a 5-minute drive of Okemo Mountain Resort and Sunshine Ski Lift.
Opens in a new windowFabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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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$956 per night from 21 Sept to 22 Sept
AU$956
21 Sept - 22 Sept
includes taxes & fees
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 ...
Opens in a new windowYour Vermont Mountain Haven Pet Friendly home with Hot tub!
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

Plymouth
Located in Plymouth, this vacation home is in the mountains, within a 15-minute drive of Long Trail Brewing Company and Coolidge State Park.
Opens in a new windowDog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!

Winhall
With a stay at this vacation home in Winhall, you'll be within a 5-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
Opens in a new windowCozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Andover
Located in Ludlow, this vacation home is on the waterfront, within a 15-minute drive of Green Mountain National Forest and Mill Museum.
Opens in a new windowSecluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the ...
Opens in a new windowTraveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

Peru
With a stay at this vacation home in Peru (Bromley Mountain), you'll be steps from Green Mountain National Forest and 8 minutes by foot from Bromley Mountain ...
Opens in a new windowBeautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
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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
1139 Holiday Homes
Lowest Price
AU$260
Highest Price
AU$1,056
Popular accommodation
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Idyllic Lakefront House Suited Two Families, Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location, Your Vermont Mountain Haven Pet Friendly home with Hot tub!, Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi, Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!, Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

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$260 per night from 19 Oct to 20 Oct
AU$260
19 Oct - 20 Oct
includes taxes & fees
Located in Chester (Chester Depot), Fullerton Inn is within a 15-minute drive of Vermont Country Store and Springfield Hospital.
Opens in a new windowFullerton Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
Opens in a new windowThe Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$1,056 per night from 21 Sept to 22 Sept
AU$1,056
21 Sept - 22 Sept
includes taxes & fees
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 ...
Opens in a new windowWoodstock 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$317 per night from 21 Sept to 22 Sept
AU$317
21 Sept - 22 Sept
includes taxes & fees
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 ...
Opens in a new windowThe 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.