Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Winhall
Located in Bondville, this vacation home is on the waterfront, within a 15-minute drive of Green Mountain National Forest and Winhall River.
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Quaint lakefront home with a fire pit and beautiful views

Quaint lakefront home with a fire pit and beautiful views

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 Green Mountain Sugar House.
Quaint lakefront home with a fire pit and beautiful 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
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 Breaktime - Quiet and Private on dead end street

Breaktime - Quiet and Private on dead end street

Manchester
With a stay at this vacation home in Manchester, you'll be a 1-minute walk from Green Mountain National Forest and 8 minutes by foot from Golf Club at ...
Breaktime - Quiet and Private on dead end street
Pet-Friendly Claremont Vacation Rental!

Pet-Friendly Claremont Vacation Rental!

Claremont
With a stay at this vacation home in Claremont, you'll be within a 10-minute walk of Holy Resurrection Orthodox Church and Barnes Park.
Pet-Friendly Claremont Vacation Rental!
Ski-in/out home with a hot tub, fireplace, cable & golf nearby

Ski-in/out home with a hot tub, fireplace, cable & golf nearby

Ludlow
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 Red Lot.
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock
Located in Woodstock, this vacation home is in a rural location, within a 10-minute drive of Union Arena Community Center and Five Elm Arches.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Westmoreland
Located in Westmoreland, this vacation home is in a rural location, within a 10-minute drive of Connecticut River and Pierces Island State Park.
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
Heated Saltwater Pool: Riverfront Home in Ludlow

Heated Saltwater Pool: Riverfront Home in Ludlow

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 Jackson Gore Parking.
Heated Saltwater Pool: Riverfront Home in Ludlow
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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$234
Highest Price
AU$763
Popular accommodation
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond, Quaint lakefront home with a fire pit and beautiful views, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Breaktime - Quiet and Private on dead end street, Pet-Friendly Claremont Vacation Rental!, Ski-in/out home with a hot tub, fireplace, cable & golf nearby, PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC., Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!, Heated Saltwater Pool: Riverfront Home in Ludlow

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$234 per night from 1 Sept to 2 Sept
AU$234
1 Sept - 2 Sept
includes taxes & fees
Located in Chester (Chester Depot), Fullerton Inn is within a 15-minute drive of Vermont Country Store and Springfield Hospital.
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$763 per night from 1 Sept to 2 Sept
AU$763
1 Sept - 2 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 ...
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$316 per night from 10 Aug to 11 Aug
AU$316
10 Aug - 11 Aug
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 ...
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.