Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Quiet Modern Luxury Home w/  Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater
With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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$590 per night from 3 Dec to 4 Dec
AU$590
includes taxes & fees
3 Dec - 4 Dec
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
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
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Plenty of Room For Everyone! - 5 Minutes to Stratton

Plenty of Room For Everyone! - 5 Minutes to Stratton

Jamaica
The price is AU$1,331 per night from 25 Nov to 26 Nov
AU$1,331
includes taxes & fees
25 Nov - 26 Nov
With a stay at this vacation home in Winhall, you'll be on a river, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
Plenty of Room For Everyone! - 5 Minutes to Stratton
Slopeside Chalet - Ski to and from your home!

Slopeside Chalet - Ski to and from your home!

Killington
The price is AU$1,108 per night from 25 Nov to 26 Nov
AU$1,108
includes taxes & fees
25 Nov - 26 Nov
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 4-minute drive from Bear Mountain Quad ...
Slopeside Chalet - Ski to and from your home!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village ...
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
77 Okemo Ridge Rd, Ludlow, VT
With a stay at Okemo Mountain Lodging in Ludlow (Clock Tower Base Area), you'll be within a 10-minute walk of Okemo Mountain Resort and General Parking.
Okemo Mountain Lodging
Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

Manchester
Located in Manchester, this vacation home is next to a golf course, within a 5-minute walk of Green Mountain National Forest and Golf Club at Equinox.
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Dog-friendly chalet cabin with valley view, deck, and private hot tub

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Dog-friendly chalet cabin with valley view, deck, and private hot tub
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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
870 Holiday Homes
Lowest Price
AU$232
Highest Price
AU$1,331
Popular accommodation
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Plenty of Room For Everyone! - 5 Minutes to Stratton, Slopeside Chalet - Ski to and from your home!, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, Okemo Mountain Lodging, Miner Cottage-Historic Antique Home just steps from the Equinox Resort, Dog-friendly chalet cabin with valley view, deck, and private hot tub

Top trending hotels in Chester

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
The price is AU$375 per night from 5 Dec to 6 Dec
AU$375
includes taxes & fees
5 Dec - 6 Dec
With a stay at Stone Hearth Inn and Eatery in Chester, you'll be 8.5 mi (13.7 km) from Vermont Country Store and 11 mi (17.6 km) from Magic Mountain Ski ...
Stone Hearth Inn and Eatery
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$591 per night from 16 Dec to 17 Dec
AU$591
includes taxes & fees
16 Dec - 17 Dec
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
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is AU$232 per night from 8 Dec to 9 Dec
AU$232
includes taxes & fees
8 Dec - 9 Dec
A stay at Hampton Inn and Suites Manchester places you in the heart of Manchester Center, steps from Green Mountain National Forest and 8 minutes by foot from ...
Hampton Inn and Suites Manchester
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Kimpton Taconic Hotel, an IHG Hotel

Kimpton Taconic Hotel, an IHG Hotel

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is AU$339 per night from 16 Dec to 17 Dec
AU$339
includes taxes & fees
16 Dec - 17 Dec
With a stay at Kimpton Taconic Hotel, an IHG Hotel in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and ...
Kimpton Taconic Hotel, an IHG Hotel
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.