Windsor 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 Windsor
Brookside cottage near the mountains and outdoor recreation
Readsboro VT
Located in Readsboro, this cottage is on a river, a 1-minute drive from Green Mountain National Forest and 9 minutes from Readsboro Town Hall.
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.
Pool
Kitchen
Quiet All-season Creekside Escape in Upstate!
Berlin NY
Located in Berlin, this cottage is within a 15-minute drive of Cherry Plain State Park and Zema's Nursery.
Kitchen
Dryer
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
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
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
Spacious Historic Home in the Berkshires!
Pittsfield MA
With a stay at this cottage in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Colonial Theater.
Kitchen
Washer
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.
Kitchen
Washer
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
Berkshires farm, 30+ guests, 50 acres
New Lebanon NY
$1,808 nightly
The price is $1,832 total per night
$1,832 total
Apr 7 - Apr 8
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
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 | $1,832 |
Highest Price | $1,832 |
Popular accommodation | Brookside cottage near the mountains and outdoor recreation, The Clearing - Quiet - Close To Nature, Quiet All-season Creekside Escape in Upstate!, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!, Charming historic cottage on scenic road to Mt. Greylock, Spacious Historic Home in the Berkshires!, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!, Berkshires farm, 30+ guests, 50 acres, Cavalier Cottage B&B, Cottage in the Clouds With Mountain Views |