Pittsfield Cottages

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Cottages in Pittsfield

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

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

Cozy cottage with pool, walking distance to lake

Averill Park NY

With a stay at this cottage in Averill Park, you'll be on a lake, a 3-minute walk from Burden Lake and a 2-minute drive from Crooked Lake.

Pool

Kitchen

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

Cozy Cottage-Sunset On The Lake

Otis MA

$514 nightly

$574 total

Oct 23 - Oct 24

Total with taxes and fees

When you stay at this cottage in Otis, you'll be on a lake, within a 5-minute drive of County Beach and Handle Tow.

Kitchen

Washer

Quiet Get Away on the Lake! Kayaks,life vests ,Fishing Equipments ,golf clubs

Valatie NY

Located in Valatie, this cottage is on a lake, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.

Kitchen

Washer

LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

Monterey MA

Located in Monterey, this cottage is a 1-minute drive from Lake Garfield and 7 minutes from Bidwell House Museum.

Washer

Dryer

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.

Kitchen

Pet friendly

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$2,034 nightly

$2,064 total

Nov 19 - Nov 20

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.

Hot Tub

Kitchen

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

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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.