Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

4 Season Secluded Lakefront Home near Ski Mountains

4 Season Secluded Lakefront Home near Ski Mountains

Mt Holly VT
Located in Mount Holly, this vacation home is on the waterfront, within a 15-minute drive of Lake Ninevah and Buttermilk Falls.
Opens in a new window4 Season Secluded Lakefront Home near Ski Mountains
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base

Ludlow VT
With a stay at this vacation home in Ludlow, you'll be in the mountains, within a 10-minute drive of Okemo Mountain Resort and Dorsey Park.
Opens in a new windowCozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base
Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub

Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub

2 out of 5
Peru VT
With a stay at this vacation home in Peru (Bromley Mountain), you'll be steps from Green Mountain National Forest and 10 minutes by foot from Bromley Mountain ...
Opens in a new windowBeautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub
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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 VT
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
Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Plymouth VT
With a stay at this vacation home, you'll be centrally located in Plymouth, within a 10-minute drive of Amherst Lake and Echo Lake.
Opens in a new windowRustic home with a private hot tub, fireplace, cable, & washer/dryer
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 VT
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
 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
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.
Opens in a new window 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Bridgewater Corners VT
When you stay at this vacation home in Bridgewater Corners, you'll be on a lake, within a 15-minute drive of Killington Resort and Pico Mountain at Killington ...
Opens in a new windowNewly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Ski in Ski out Condo! Pool access

Ski in Ski out Condo! Pool access

Stratton VT
The price is AU$866 per night from 4 Feb to 5 Feb
AU$866
4 Feb - 5 Feb
includes taxes & fees
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 ...
Opens in a new windowSki in Ski out Condo! Pool access
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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
944 Holiday Homes
Lowest Price
AU$202
Highest Price
AU$866
Popular accommodation
4 Season Secluded Lakefront Home near Ski Mountains , Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base, Beautifully Remodeled VT Mountain Oasis with Stratton Views and private Hot Tub, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Rustic home with a private hot tub, fireplace, cable, & washer/dryer, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base, Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola, Ski in Ski out Condo! Pool access

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$202 per night from 1 Mar to 2 Mar
AU$202
1 Mar - 2 Mar
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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is AU$277 per night from 1 Mar to 2 Mar
AU$277
1 Mar - 2 Mar
includes taxes & fees
With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School ...
Opens in a new windowPointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is AU$551 per night from 22 Feb to 23 Feb
AU$551
22 Feb - 23 Feb
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
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Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
The price is AU$325 per night from 2 Mar to 3 Mar
AU$325
2 Mar - 3 Mar
includes taxes & fees
With a stay at Kimpton Taconic Hotel by IHG in Manchester (Manchester Village Historic District), you'll be steps from Green Mountain National Forest and 5 minutes ...
Opens in a new windowKimpton Taconic Hotel by IHG
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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.