Pittsfield Cottages
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Cottages in Pittsfield
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
New Marlborough MA
Located in Great Barrington, this cottage is on a lake, within a 5-minute drive of Lake Buel and Les Trois Emme Winery.
Kitchen
Washer
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
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Valatie NY
Located in Valatie, this cottage is on a lake, a 1-minute drive from Kinderhook Lake and 7 minutes from Valatie Free Library.
Kitchen
Pet friendly
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
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 Sand Lake Center for the Arts and Berkshire Retreat Center.
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
Private Island - Largest Fresh Water Reservoir in Mass
Otis MA
With a stay at this cottage in Otis, you'll be on the waterfront, just steps from Otis Reservoir and a 4-minute drive from Larkum Pond.
Kitchen
Pet friendly
Waterfront Cottage 10 Min From Great Barrington
New Marlborough MA
With a stay at this cottage in Great Barrington, you'll be steps from Lake Buel and a 4-minute drive from Les Trois Emme Winery.
Kitchen
Washer
Waterfalls and Trails at 'the Mills At Green Hole'
Hillsdale NY
With a stay at this cottage in Hillsdale, you'll be within a 15-minute drive of High Falls Trail and Claverack Library.
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.
Pittsfield Cottages essential information
Accommodation | 111 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , The Clearing - Quiet - Close To Nature, Heaven Can't Wait, On Beautiful Kinderhook Lake!!, Quiet All-season Creekside Escape in Upstate!, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Cozy cottage with pool, walking distance to lake, Charming historic cottage on scenic road to Mt. Greylock, Private Island - Largest Fresh Water Reservoir in Mass, Waterfront Cottage 10 Min From Great Barrington, Waterfalls and Trails at 'the Mills At Green Hole', Spacious Historic Home in the Berkshires!, Lakefront Berkshires Retreat w/ Deck, Dock & Boat! |