The Berkshires holiday rentals

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Best The Berkshires holiday rentals

Most recommended holiday rentals in The Berkshires

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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
RM 2,003+
Check 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
RM 1,674+
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
RM 5,218+
Check availability
Sunsets On Blue Hill, Newly Renovated Farmhouse - Great Barrington - Living room
Sunsets On Blue Hill, Newly Renovated Farmhouse
Great Barrington, MA, United States
RM 4,560+
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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
RM 3,738+
Check availability
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
RM 2,020+
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Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
RM 1,350+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
RM 1,367+
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Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.9Wonderful(13)
Free Wi-Fi
Pet-friendly
RM 1,627+
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Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town - Great Barrington - Dining room
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town
Great Barrington, MA, United States
7.0Good(3)
Parking
Free Wi-Fi
Pet-friendly
RM 2,042+
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Heart of Lenox!! - renovated downtown apartment - Lenox - Kitchen
Heart of Lenox!! - renovated downtown apartment
Lenox, MA, United States
RM 1,891+
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A four-season forest cabin - Great Barrington - Living room
A four-season forest cabin
Great Barrington, MA, United States
Spa
RM 3,228+
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Perfect location in the heart of downtown Lenox - Lenox - Living room
Perfect location in the heart of downtown Lenox
Lenox, MA, United States
Free Wi-Fi
RM 2,124+
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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
RM 1,307+
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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
RM 1,367+
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Great Barrington apartment, Short walk to downtown - Great Barrington
Great Barrington apartment, Short walk to downtown
Great Barrington, MA, United States
RM 1,480+
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RM 0 - RM 5,071RM 5,071 - RM 10,137RM 10,137 - RM 15,203RM 15,203 - RM 20,269RM 20,269+ per night

Property type

ApartmentCondoCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

September

High season

December

Average price (weeknight)

RM 3,642

Average price (weekend night)

RM 1,095
Cheapest month to stay with an average 55% drop in price.
Most expensive month to stay with an average 637% 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 RM 1,797. 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 and campgrounds.

  • 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.

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