New Ashford Cottages

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Cottages in New Ashford

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Charlemont MA

With a stay at this cottage in Charlemont, you'll be within a 15-minute drive of Deerfield River and Zoar Outdoor/Deerfield Valley Canopy Tours.

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.

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.

Massachusetts Vacation Rental w/ Deck & Grill

Windsor MA

With a stay at this cottage in Windsor, you'll be 8.1 mi (13 km) from Susan B. Anthony Birthplace Museum and 8.2 mi (13.2 km) from Tannery Falls.

Kitchen

Washer

Bennington Gem w/ Smart TV Near Historic District!

Bennington VT

With a stay at this cottage in Bennington, you'll be within a 5-minute walk of Green Mountain National Forest and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display.

Kitchen

Washer

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Nassau NY

Located in Nassau, this cottage is on the waterfront, within a 15-minute drive of Berkshire Retreat Center and Kinderhook Lake.

Kitchen

Free WiFi

Berkshires farm, 30+ guests, 50 acres

New Lebanon NY

$2,013 nightly

$2,033 total

Dec 21 - Dec 22

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.

Charlemont Retreat on Chickley River w/ EV Charger

Charlemont MA

Located in Charlemont, this cottage is within a 15-minute drive of Zoar Outdoor/Deerfield Valley Canopy Tours and Berkshire East Ski Resort.

Luxury Vacation Rental in the Berkshires!

Williamstown MA

Located in Williamstown, this cottage is within a 5-minute drive of Mount Greylock State Reservation and Lower Linear Park.

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 Berkshire Retreat Center and Pineridge Cross Country Ski Center.

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

856 Streeter Hill Rd Whitingham VT

When you stay at this cottage in Whitingham, you'll be within a 10-minute drive of Harriman Reservoir and Jacksonville Pond.

Cozy Berkshire cottage with fireplace.

Pittsfield MA

With a stay at this cottage in Pittsfield, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Colonial Theater.

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.