The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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£42 - £313£313 - £584£584 - £855£855 - £1,127£1,127+ per night

Property Types

ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in The Berkshires

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Econo Lodge - Lee - Bedroom
Econo Lodge
Lee, MA, United States
5.6Fair(425)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£71+
Check availability
Elegant 19th Century New England Newly Renovated 1br Vacation Rental - Lee - Patio
Elegant 19th Century New England Newly Renovated 1br Vacation Rental
Lee, MA, United States
Pet-friendly
Air conditioning
£160+
Check availability
Water Street Apartments - Williamstown - Living room
Water Street Apartments
Williamstown, MA, United States
9.4Wonderful(14)
Parking
Free Wi-Fi
Air conditioning
£182+
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Nestled minutes from Main Street, Great Barrington - Great Barrington
Nestled minutes from Main Street, Great Barrington
Great Barrington, MA, United States
Air conditioning
£221+
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Villa with Access to Various Amenities - Lee - Dining room
Villa with Access to Various Amenities
Lee, MA, United States
Free Wi-Fi
Pool
Air conditioning
£227+
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Stockbridge Vacation by Norman Rockwell - Stockbridge - Restaurant
Stockbridge Vacation by Norman Rockwell
Stockbridge, MA, United States
Pet-friendly
Air conditioning
£246+
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Gateway to the Berkshires - Renovated downtown apartment - Lee - Bedroom
Gateway to the Berkshires - Renovated downtown apartment
Lee, MA, United States
Free Wi-Fi
Air conditioning
£268+
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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
Air conditioning
£370+
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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
Air conditioning
£401+
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Perfect Great Barrington Spot, Nature, and Views! - Great Barrington
Perfect Great Barrington Spot, Nature, and Views!
Great Barrington, MA, United States
Air conditioning
£405+
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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
Air conditioning
£432+
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5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 ! - Great Barrington - Property amenity
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !
Great Barrington, MA, United States
9.7Wonderful(34)
Pool
Air conditioning
£482+
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1780 Colonial Hilltop Manor - Amazing location - Stockbridge - Patio
1780 Colonial Hilltop Manor - Amazing location
Stockbridge, MA, United States
Air conditioning
£521+
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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
Air conditioning
£528+
Check availability
Secluded 19th century Farmhouse with mountain views - North Adams - Building
Secluded 19th century Farmhouse with mountain views
North Adams, MA, United States
£547+
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Cabin Fever In Stockbridge - Stockbridge - Living room
Cabin Fever In Stockbridge
Stockbridge, MA, United States
Air conditioning
£629+
Check availability
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Good to know

Low season

June

High season

December

Average price (weeknight)

£410

Average price (weekend night)

£247
Cheapest month to stay with an average 42% drop in price.
Most expensive month to stay with an average 509% 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 holiday home in The Berkshires

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

    In the last 72 hours, users have found The Berkshires holiday rentals for tonight for as little as £268. Search here for similar prices

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

    There are loads of different property types that you can make your holiday home in The Berkshires. You’ll find agritourism, apartments, cabins, caravan parks, chalets, condos, cottages, houses, lodges, villas, campgrounds, farm stays and homestays.

  • What are some of the most-loved holiday rentals available in The Berkshires?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Econo Lodge.

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

    There are a number of dog and pet-friendly The Berkshires holiday 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 holiday home.

Everything you need to know for your stay in The Berkshires

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