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
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.
Kitchen
Washer
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
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
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.
Kitchen
Washer
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.
Kitchen
Washer
Berkshires farm, 30+ guests, 50 acres
New Lebanon NY
$2,096 nightly
The price is $2,125 total per night
$2,125 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.
Hot Tub
Kitchen
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.
Kitchen
Washer
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.
Kitchen
Washer
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.
Pool
Kitchen
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.
Windsor Cottages essential information
Accommodation | 74 Cottages |
|---|---|
Lowest Price | $2,125 |
Highest Price | $2,125 |
Popular accommodation | The Clearing - Quiet - Close To Nature, Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck & Grill, Historic Huntington Home - Walk to Westfield River, Berkshires farm, 30+ guests, 50 acres, Charlemont Retreat on Chickley River w/ EV Charger, Luxury Vacation Rental in the Berkshires!, Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!, Cavalier Cottage B&B, Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge! |