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

Classic ski home with hot tub, washer/dryer, mountain views, & 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.

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish VT

With a stay at this vacation home in Cavendish, you'll be within a 15-minute drive of Okemo Mountain Resort and Phineas Gage Memorial.

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham VT

With a stay at this vacation home, you'll be centrally located in West Townshend, within a 15-minute drive of Lowell Lake State Park and Magic Mountain Ski Resort.

Idyllic Lakefront House Suited Two Families

Ludlow VT

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

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Manchester VT

With a stay at this vacation home in Manchester, you'll be in the mountains, just a 1-minute walk from Green Mountain National Forest and 12 minutes by foot from Museum of Creative Process.

Kitchen

Free WiFi

3 Levels w/ Magnificent Mountain Views, 5 Mins to Stratton Base, Sauna, Firepit

Winhall VT

With a stay at this vacation home in Bondville, you'll be in the mountains, within a 10-minute drive of Stratton Mountain Resort and Winhall River.

Kitchen

Washer

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Manchester Center VT

With a stay at this vacation home in Manchester Center, you'll be on a river, just steps from Green Mountain National Forest and a 3-minute drive from Lye Brook Falls Trailhead.

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT

With a stay at this vacation home in Jamaica (Pikes Falls), you'll be within a 15-minute drive of Stratton Mountain Resort and Solstice Ski Lift.

Kitchen

Washer

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro VT

With a stay at this vacation home in Wardsboro, you'll be next to a golf course, within a 15-minute drive of Mount Snow and Wardsboro Public Library.

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.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

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.

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Ludlow VT

With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 10-minute drive of Okemo Mountain Resort and Lake Rescue.

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.