Book Holiday Homes in Chester

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chester

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend, VT
Located in Townshend, this vacation home is in the mountains, within a 15-minute drive of West River and Newfane Town Hall.
Opens in a new windowLuxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
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
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
Save an average of 15% on thousands of hotels when you're signed in
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Weston
The price is AU$1,384 per night from 19 Nov to 20 Nov
AU$1,384
19 Nov - 20 Nov
includes taxes & fees
Located in Weston, this vacation home is on a river, a 1-minute drive from West River and 5 minutes from West River Farmers Market.
Opens in a new windowCharming mountain retreat with pool, fire pit, glamping loft, and endless views
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 ...
Opens in a new windowQuiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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.
Opens in a new windowOkemo Mountain Lodging
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$965 per night from 4 Nov to 5 Nov
AU$965
4 Nov - 5 Nov
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!
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Ludlow
When you stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute walk of Okemo Mountain Resort and Sunshine Ski Lift.
Opens in a new windowClassic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

South Londonderry
The price is AU$754 per night from 4 Nov to 5 Nov
AU$754
4 Nov - 5 Nov
includes taxes & fees
When you stay at this vacation home in South Londonderry, you'll be on a lake, within a 5-minute drive of Magic Mountain Ski Resort and Lowell Lake State ...
Opens in a new windowMtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Don't see what you're looking for?
See all available properties in Chester
View all properties
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
949 Holiday Homes
Lowest Price
AU$326
Highest Price
AU$1,384
Popular accommodation
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC, Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Charming mountain retreat with pool, fire pit, glamping loft, and endless views, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Okemo Mountain Lodging, Your Vermont Mountain Haven Pet Friendly home with Hot tub!, Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table, Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

Top trending hotels in Chester

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$603 per night from 30 Nov to 1 Dec
AU$603
30 Nov - 1 Dec
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
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
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
The price is AU$345 per night from 4 Nov to 5 Nov
AU$345
4 Nov - 5 Nov
includes taxes & fees
With a stay at Jackson Gore Village in Ludlow (Jackson Gore Base Area), you'll be within a 15-minute walk of Okemo Mountain Resort and Jackson Gore Parking.
Opens in a new windowJackson Gore Village
Save an average of 15% on thousands of hotels when you're signed in
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$326 per night from 1 Dec to 2 Dec
AU$326
1 Dec - 2 Dec
includes taxes & fees
With a stay at Kimpton Taconic Hotel by IHG in Manchester, you'll be next to a golf course, just a 1-minute walk from Green Mountain National Forest and 5 minutes ...
Opens in a new windowKimpton Taconic Hotel by IHG
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.