Chester Cottages

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

Check dates for Chester hotels

Cottages in Chester

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Winhall VT

With a stay at this cottage, you'll be centrally located in Winhall, within a 5-minute drive of Bromley Mountain Ski Resort and Green Mountain National Forest.

Kitchen

Washer

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

Dorset VT

With a stay at this cottage in Dorset, you'll be in the mountains, just a 1-minute walk from Green Mountain National Forest and 5 minutes by foot from Dorset Playhouse.

Kitchen

Washer

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Ludlow VT

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

Hot Tub

Kitchen

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington VT

With a stay at this cottage in Wilmington, you'll be near the beach, just a 1-minute walk from Lake Raponda and 12 minutes by foot from The Art of Humor Gallery.

Kitchen

Washer

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Chester VT

Located in Chester, this cottage is within a 15-minute drive of Vermont Country Store and DaVallia Art & Accents.

Kitchen

Washer

Cozy Historic Hilltop Cottage with Mount Ascutney View

West Windsor VT

Located in Windsor, this cottage is in the mountains, within a 15-minute drive of Mt Ascutney State Park and Brownsville Trail.

Pool

Kitchen

Vermont Country Cottage (Near Village)

Londonderry VT

With a stay at this cottage in Londonderry, you'll be in the mountains, within a 15-minute drive of Bromley Mountain Ski Resort and West River.

Kitchen

Washer

Enchanting 4-bedroom cottage with a view in Weston

Weston VT

With a stay at this cottage in Weston, you'll be a 1-minute walk from Green Mountain National Forest and 7 minutes by foot from West River.

Kitchen

Washer

Home with a spring-fed pond and mountain view.

Manchester VT

With a stay at this cottage in Manchester Center, you'll be on the waterfront, just steps from Green Mountain National Forest and a 3-minute drive from Golf Club at Equinox.

Breakfast included

Kitchen

Near Skiing & Hiking: Quiet Home in West Wardsboro

West Wardsboro VT

With a stay at this cottage in West Wardsboro, you'll be within a 10-minute drive of Mount Snow and Green Mountain National Forest.

Kitchen

Washer

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Reading VT

When you stay at this cottage in Reading, you'll be on a river and 11 minutes by car from Mt Ascutney State Park.

Kitchen

Washer

Pet-friendly Claremont Vacation Rental!

Claremont NH

With a stay at this cottage in Claremont, you'll be within a 10-minute walk of Holy Resurrection Orthodox Church and Barnes Park.

Kitchen

Washer

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.