Monterey Cottages
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Cottages in Monterey
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 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
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
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Winsted CT
With a stay at this cottage in Winsted, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 9 minutes by foot from The Marina at Highland Lake.
Kitchen
Free WiFi
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Ashley Falls MA
Located in Ashley Falls, this cottage is within a 5-minute drive of Ashley Falls Woods and Bartholomew's Cobble.
Kitchen
Parking included
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
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
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
325 Long Pond Road Great Barrington MA
Located in Great Barrington, this cottage is within a 10-minute drive of Art et Industrie and Housatonic River.
Kitchen
Washer
Historic Huntington Home - Walk to Westfield River
Huntington MA
With a stay at this cottage in Huntington, you'll be within a 5-minute drive of Huntington Public Library and Hillgate Park.
Kitchen
Washer
Light-filled cottage
New Marlborough MA
Located in New Marlborough, this cottage is on a lake, within a 15-minute drive of Cookson State Forest and Dry Hill.
Hot Tub
Kitchen
Berkshires farm, 30+ guests, 50 acres
New Lebanon NY
$2,096 nightly
The price is $2,125 total per night
$2,125 total
Jan 5 - Jan 6, 2026
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.
Monterey Cottages essential information
Accommodation | 103 Cottages |
|---|---|
Lowest Price | $2,125 |
Highest Price | $2,125 |
Popular accommodation | Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , The Blue Elm - A Historic Berkshire Cottage, Waterfront Cottage 10 Min From Great Barrington, The Cottage at Highland Lake, year-round, waterfront with a boat dock , Ashley Falls Home w/ Fire Pit: Hike & Ski!, Private Island - Largest Fresh Water Reservoir in Mass, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, Historic Huntington Home - Walk to Westfield River, Light-filled cottage, Berkshires farm, 30+ guests, 50 acres, Elegant Hudson Valley Retreat w/ Hot Tub & Pond |