Cheshire 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 Cheshire hotels

Cottages in Cheshire

The Clearing - Quiet - Close To Nature

Cummington MA

Located in Cummington, this cottage is in a rural location, a 1-minute drive from Westfield River and 8 minutes from Chesterfield Gorge Reservation.

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Charlemont MA

With a stay at this cottage in Charlemont, you'll be within a 15-minute drive of Deerfield River and Zoar Outdoor/Deerfield Valley Canopy Tours.

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Canaan NY

Located in Canaan, this cottage is on the waterfront, a 3-minute drive from Queechy Lake and 7 minutes from Furnace Brook Winery at Hilltop Orchards.

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA

With a stay at this cottage in Lanesborough, you'll be in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State Reservation.

Massachusetts Vacation Rental w/ Deck & Grill

Windsor MA

With a stay at this cottage in Windsor, you'll be 8.1 mi (13 km) from Susan B. Anthony Birthplace Museum and 8.2 mi (13.2 km) from Tannery Falls.

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$2,005 nightly

$2,033 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at Berkshires farm, 30+ guests, 50 acres in New Lebanon, you'll be within a 5-minute drive of New Lebanon Library and Shatford Memorial Park.

Charlemont Retreat on Chickley River w/ EV Charger

Charlemont MA

Located in Charlemont, this cottage is within a 15-minute drive of Zoar Outdoor/Deerfield Valley Canopy Tours and Berkshire East Ski Resort.

Luxury Vacation Rental in the Berkshires!

Williamstown MA

Located in Williamstown, this cottage is within a 5-minute drive of Mount Greylock State Reservation and Lower Linear Park.

Cozy cottage with pool, walking distance to lake

Averill Park NY

Located in Averill Park, this cottage is on a lake, within a 15-minute drive of Berkshire Retreat Center and Pineridge Cross Country Ski Center.

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

856 Streeter Hill Rd Whitingham VT

When you stay at this cottage in Whitingham, you'll be within a 10-minute drive of Harriman Reservoir and Jacksonville Pond.

Cavalier Cottage B&B

236 East Oxbow Road Shelburne Falls MA

Located in Shelburne Falls, this cottage is on the riverwalk, a 4-minute drive from Deerfield River and 8 minutes from Bald Mountain Pottery.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

21 Saint James Avenue Lee MA

With a stay at this cottage in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.

Don't see what you're looking for?

See all available properties in Cheshire

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.