Monterey Cottages

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Cottages in Monterey

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

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA

Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.

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

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

Craryville NY

Located in Copake Lake, this cottage is on a lake, a 1-minute drive from Copake Lake and 7 minutes from Mosquito Island.

Washer

Dryer

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

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

Waterfront Cottage at Highland Lake w/dock

Winsted CT

A stay at this cottage places you in the heart of Winsted, steps from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.

Kitchen

Free WiFi

Our Cottage - Small in size, Big in character, On beautiful Highland Lake

Winchester CT

A stay at this cottage places you in the heart of Winsted, steps from Highland Lake and a 2-minute drive from The Marina at Highland Lake.

Kitchen

Free WiFi

Fun Getaway Lakehouse in the Hudson Valley

Craryville NY

Located in Copake Lake, this cottage is on a lake, a 1-minute drive from Copake Lake and 7 minutes from Mosquito Island.

Kitchen

Washer

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$1,963 nightly

$1,983 total

Oct 7 - Oct 8

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.