Hillsdale Vacation Rentals

Name: Amore Estate - beautiful room with many places to explore and relax in.
Address: Lenox

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Vacation Rentals in Hillsdale

Hamptons on the Hudson in South Saugerties

With a stay at this vacation home, you'll be centrally located in Glasco, just a 3-minute walk from Hudson River and 11 minutes by foot from Falling Waters Preserve.

Pool

Hot Tub

Lakefront Luxe: Private Dock, Game Rm, Near Hudson

Located in Coxsackie, this vacation home is on the waterfront, a 1-minute drive from Sleepy Hollow Lake and 6 minutes from Hudson River Islands State Park.

Spectacular views and close to Great Barrington.

Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.

Berkshire Village Carriage House - Super Private!!

$223

includes taxes & fees

$200 per night

Dec 30 - Dec 31

Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.

Antique Farmhouse Totally Restored

Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Mount Riga State Park and Mount Everett State Reservation.

Berkshire Ski House on Lake Garfield w/HT By Great Barrington

Located in Monterey, this vacation home is within a 5-minute drive of Beartown State Forest and Bidwell House Museum.

Beautiful Berkshire Farm House on 160+ Acres

Located in Great Barrington, this vacation home is on the waterfront, within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Charming cottage with lake access, wood burning fire place, and WiFi

When you stay at this vacation home in Elizaville, you'll be 9 minutes by car from Tousey Winery.

Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

When you stay at this vacation home in Malden, you'll be on a river, within a 15-minute walk of George J. Terpening Sr. Memorial Park and Bristol Beach State Park.

Private Estate, Heated YEARROUND Outdoor Pool

With a stay at this vacation home in Great Barrington, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts Center.

Quintessential 6-BR Berkshires Lodge

When you stay at this vacation home in Becket, you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.

Amore Estate - beautiful room with many places to explore and relax in.

With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.

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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.