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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$2,113 nightly

$2,137 total

Sep 9 - Sep 10

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.

Berkshire summer camp!

Canaan NY

With a stay at this cottage in Canaan, you'll be steps from Queechy Lake and a 4-minute drive from Furnace Brook Winery at Hilltop Orchards.

Kitchen

Pet friendly

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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.