The Berkshires vacation rentals

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Best The Berkshires vacation rentals

Most recommended vacation rentals in The Berkshires

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Stockbridge Home Walk to Town Beach! - Stockbridge - Living room
Stockbridge Home Walk to Town Beach!
Stockbridge, MA, United States
9.1Wonderful(8)
Free Wi-Fi
₱17,997+
Check availability
Stockbridge Vacation by Norman Rockwell - Stockbridge - Restaurant
Stockbridge Vacation by Norman Rockwell
Stockbridge, MA, United States
Pet friendly
₱18,957+
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Classic Stockbridge Cottage - Stockbridge - Building
Classic Stockbridge Cottage
Stockbridge, MA, United States
Parking
Free Wi-Fi
Pet friendly
₱26,905+
Check availability
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing - Stockbridge - Living room
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing
Stockbridge, MA, United States
Pet friendly
₱68,379+
Check availability
1780 Colonial Hilltop Manor - Amazing location - Stockbridge - Patio
1780 Colonial Hilltop Manor - Amazing location
Stockbridge, MA, United States
₱40,170+
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Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood) - Stockbridge - Living room
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
Stockbridge, MA, United States
Pet friendly
₱17,715+
Check availability
The Great Escape Ski Cottage W/Hot Tub @ Great Barrington - Great Barrington - Living room
The Great Escape Ski Cottage W/Hot Tub @ Great Barrington
Great Barrington, MA, United States
Free Wi-Fi
Spa
₱68,040+
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Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) - Stockbridge - Living room
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Stockbridge, MA, United States
Free Wi-Fi
Pet friendly
₱16,474+
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Lovely two bedroom river-view rental unit - Williamstown - Living room
Lovely two bedroom river-view rental unit
Williamstown, MA, United States
9.2Wonderful(15)
₱21,439+
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Water Street Apartments - Williamstown - Living room
Water Street Apartments
Williamstown, MA, United States
9.4Wonderful(11)
Free Wi-Fi
₱12,920+
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Historic Retreat - Stockbridge
Historic Retreat
Stockbridge, MA, United States
Parking
₱24,711+
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Escape To Stockbridge|ski & Explore|the Berkshires| - Stockbridge
Escape To Stockbridge|ski & Explore|the Berkshires|
Stockbridge, MA, United States
Free Wi-Fi
Pet friendly
₱40,734+
Check availability
Autumn Leaves Of Scarlet And Gold With Evenings Of Warm Drinks - Lenox
Autumn Leaves Of Scarlet And Gold With Evenings Of Warm Drinks
Lenox, MA, United States
₱33,343+
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Spectacular Housatonic River View from newly renovated Historic Cottage - Stockbridge
Spectacular Housatonic River View from newly renovated Historic Cottage
Stockbridge, MA, United States
Free Wi-Fi
₱28,548+
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Pet-Friendly Bell Tent with Views of Taconic Mountains for a Great Escape in Nature in Petersburg, New York - Williamstown
Pet-Friendly Bell Tent with Views of Taconic Mountains for a Great Escape in Nature in Petersburg, New York
Williamstown, MA, United States
Pet friendly
₱13,822+
Check availability
Clover Hill Farm & Country Inn - Williamstown
Clover Hill Farm & Country Inn
Williamstown, MA, United States
9.6Wonderful(13)
Parking
Free Wi-Fi
Pet friendly
₱8,463+
Check availability
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₱5,811 - ₱70,466₱70,466 - ₱135,065₱135,065 - ₱199,721₱199,721 - ₱264,319₱264,319+ per night

Property Types

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Good to know

Low season

November

High season

December

Average price (weeknight)

₱100,735

Average price (weekend night)

₱29,785
Cheapest month to stay with an average 68% drop in price.
Most expensive month to stay with an average 337% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a vacation home in The Berkshires

  • How much is a vacation rental in The Berkshires for tonight?

    In the last 72 hours, users have found The Berkshires vacation rentals for tonight for as low as ₱28,611. Search here for similar prices

  • What types of vacation rentals are available in The Berkshires?

    There are loads of different property types that you can make your vacation home in The Berkshires. You’ll find apartments, cabins, campgrounds, cottages, houses, farm stays and condos.

  • Are there any pet-friendly vacation rentals in The Berkshires?

    There are a number of dog and pet-friendly The Berkshires vacation rentals, with around 20% allowing you to bring your pet along with you.

Where to stay in The Berkshires?

Our map will help you find the perfect place to stay in The Berkshires by showing you the exact location of each vacation home.

Everything you need to know for your stay in The Berkshires

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