Windsor Cottages

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Cottages in Windsor

Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances

Chester MA

With a stay at this cottage in Huntington, you'll be steps from Fox Den Wildlife Management Area and a 2-minute drive from Glendale Falls.

Kitchen

Washer

Brookside cottage near the mountains and outdoor recreation

Readsboro VT

$212 nightly

$237 total

Jun 21 - Jun 22

Total with taxes and fees

Located in Readsboro, this cottage is on a river, within a 10-minute drive of Readsboro Town Hall and Readsboro Community Library.

Kitchen

Pet friendly

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.

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.

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.

Kitchen

Pet friendly

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.

Breakfast included

Kitchen

Private Lake Cottage on 3 acres w/350 sq. ft. deck

Becket MA

Located in Becket, this cottage is a 4-minute drive from Iroquis Waterfront and 8 minutes from Becket Quarry.

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$2,364 nightly

$2,395 total

Jul 7 - Jul 8

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.

Beachwood Cottage

Stockbridge MA

When you stay at this cottage in West Stockbridge, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.

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 Huntington Town Hall.

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Williamsburg MA

With a stay at this cottage in Williamsburg, you'll be within a 10-minute drive of Silvio O. Conte National Fish and Wildlife Refuge and Three Sisters Sanctuary.

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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.