The Berkshires holiday rentals

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Best The Berkshires holiday rentals

Most recommended holiday rentals in The Berkshires

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Water Street Apartments - Williamstown - Living room
Water Street Apartments
Williamstown, MA, United States
9.4Wonderful(11)
Free Wi-Fi
$358+
View availability
Vacation Rental Home in the Berkshires! - Williamstown - Living room
Vacation Rental Home in the Berkshires!
Williamstown, MA, United States
9.4Wonderful(8)
Free Wi-Fi
$411+
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Cozy Great Barrington Home about 1 Mi to Ski Resort! - Great Barrington - Bedroom
Cozy Great Barrington Home about 1 Mi to Ski Resort!
Great Barrington, MA, United States
9.8Wonderful(14)
Free Wi-Fi
$723+
View availability
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 - Great Barrington - Living room
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9
Great Barrington, MA, United States
Parking
Free Wi-Fi
Pet-friendly
$604+
View 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
$1,883+
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Sunsets On Blue Hill, Newly Renovated Farmhouse - Great Barrington - Living room
Sunsets On Blue Hill, Newly Renovated Farmhouse
Great Barrington, MA, United States
$1,646+
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Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town - Great Barrington - Living room
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town
Great Barrington, MA, United States
Parking
Free Wi-Fi
Pet-friendly
$1,349+
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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)
$593+
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Beautiful Lenox Home, 3 Mi to Shakespeare and Co! - Lenox - Living room
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
Lenox, MA, United States
9.3Wonderful(20)
Free Wi-Fi
$729+
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Cozy and quaint country cottage, walk to downtown Williamstown - Williamstown - Building
Cozy and quaint country cottage, walk to downtown Williamstown
Williamstown, MA, United States
Pet-friendly
$367+
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Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
$487+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
$493+
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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
$472+
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Clover Hill Farm & Country Inn - Williamstown
Clover Hill Farm & Country Inn
Williamstown, MA, United States
9.6Wonderful(14)
Parking
Free Wi-Fi
Pet-friendly
$234+
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1880s Home with a Postcard View - Williamstown
1880s Home with a Postcard View
Williamstown, MA, United States
4.5Mediocre(2)
$468+
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Downtown GB apartment walk to shops and restaurants - Great Barrington
Downtown GB apartment walk to shops and restaurants
Great Barrington, MA, United States
$493+
View availability
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Property type

ApartmentCondoCottageHouse

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Good to know

Low season

April

High season

December

Average price (weeknight)

$1,146

Average price (weekend night)

$554
Cheapest month to stay with an average 54% drop in price.
Most expensive month to stay with an average 654% 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 $649. 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 and farm stays.

  • 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

Holiday rentals in The Berkshires

Pittsfield holiday rentals

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