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

Cottages in Chester

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

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 steps from Lake Raponda and a 3-minute drive from Molly Stark State Park.

Kitchen

Washer

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

Winhall VT

A stay at this cottage places you in the heart of Bondville, steps from Green Mountain National Forest and a 5-minute drive from Bromley Mountain Ski Resort.

Kitchen

Washer

Woodstock Village Carriage House

Woodstock VT

With a stay at this cottage in Woodstock, you'll be on the waterfront, within a 15-minute drive of Quechee Gorge Bridge and Marsh-Billings-Rockefeller National Historical Park.

Kitchen

Washer

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

Dorset VT

When you stay at this cottage in Dorset, you'll be in the mountains, within a 10-minute walk of Dorset Playhouse and Dorset Village Public Library.

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

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 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

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

Manchester VT

With a stay at this cottage in Manchester (Manchester Village Historic District), you'll be steps from Green Mountain National Forest and 3 minutes by foot from Golf Club at Equinox.

Kitchen

Washer

Vermont Country Cottage (Near Village)

Londonderry VT

With a stay at this cottage in Londonderry, you'll be in the mountains, just a 1-minute walk from West River and 9 minutes by foot from West River Farmers Market.

Kitchen

Washer

Cozy Crescent Cottage-Lakefront-Quiet- 25 min from Mt Sunapee -Pet friendly

Lempster NH

Located in Newport, this cottage is on the waterfront, a 1-minute drive from Crescent Lake and 7 minutes from Gallop Marsh State Wildlife Management Area.

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.

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.