Windsor Cottages

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Cottages in Windsor

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.

Pool

Kitchen

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.

Kitchen

Free WiFi

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.

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$1,884 nightly

$1,910 total

Nov 2 - Nov 3

Total with taxes and fees

With a stay at this cottage in New Lebanon, you'll be within a 5-minute drive of New Lebanon Library and Shatford Memorial Park.

Pine & Paddle | Pond Access • Kayaks

Pittsfield MA

With a stay at this cottage in Richmond, you'll be on a lake, within a 15-minute drive of Tanglewood Music Center and Tracy Brook Wildlife Sanctuary.

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Charlemont MA

With a stay at this cottage in Charlemont, you'll be within a 10-minute drive of Deerfield River and Zoar Outdoor/Deerfield Valley Canopy Tours.

Kitchen

Washer

A-frame Cabin w/ Furnished Deck in Becket!

Becket MA

Located in Becket, this cottage is a 3-minute drive from Pyramid Lake and 5 minutes from Jacob's Pillow.

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.

Peaceful Cabin Close to Skiing and Hiking

Otis MA

Located in Otis, this cottage is within a 15-minute drive of Jacob's Pillow and Pyramid Lake.

Berkshire Hills Nature Lovers' Log Home Retreat

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.

Historic Huntington Home - Walk to Westfield River

Huntington MA

With a stay at this cottage in Huntington, you'll be within a 5-minute drive of Huntington Public Library and Hillgate Park.

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Richmond MA

With a stay at this cottage in Richmond, you'll be within a 15-minute drive of Tanglewood Music Center and Balderdash Cellars.

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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.