Chester Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Chester

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.

Kitchen

Washer

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.

Kitchen

Washer

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

Peru VT

With a stay at this vacation home in Peru (Bromley Mountain), you'll be within a 15-minute walk of Bromley Mountain Ski Resort and Green Mountain National Forest.

Pool

Hot Tub

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.

Hot Tub

Kitchen

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

Plymouth VT

Located in Plymouth, this vacation home is in the mountains, within a 10-minute drive of Amherst Lake and Echo Lake.

Hot Tub

Kitchen

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 Arts and Crafts.

Kitchen

Washer

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.

Kitchen

Washer

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

Bridgewater Corners VT

$362 nightly

$405 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this vacation home in Bridgewater Corners, you'll be on a lake, within a 5-minute drive of Killington Resort and Skyeship Express Gondola Stage I.

Hot Tub

Kitchen

Ski in Ski out Condo! Pool access

Stratton VT

$512 nightly

$578 total

Dec 11 - Dec 12

Total with taxes and 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 Forest.

Hot Tub

Kitchen

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

Ludlow VT

With a stay at this vacation home in Ludlow, you'll be on a lake, within a 10-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.

Hot Tub

Kitchen

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall VT

$665 nightly

$747 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Bromley Mountain Ski Resort and Green Mountain National Forest.

Hot Tub

Kitchen

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington VT

Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.

Hot Tub

Kitchen

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.