The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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€61 - €1,035€1,035 - €2,008€2,008 - €2,982€2,982 - €3,955€3,955+ per night

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ApartmentCondoCottageHouse

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Most recommended holiday rentals in The Berkshires

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Amazing 2-bedroom apartment sunny and quiet in Great Barrington - Great Barrington - Bedroom
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Great Barrington, MA, United States
9.5Wonderful(20)
Free Wi-Fi
Air conditioning
€183+
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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
Air conditioning
€267+
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Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys! - Lenox - Living room
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Lenox, MA, United States
9.3Wonderful(13)
Air conditioning
€280+
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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
Air conditioning
€289+
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Romantic Berkshires Cottage - Stunning Views, Pool - Great Barrington - Dining room
Romantic Berkshires Cottage - Stunning Views, Pool
Great Barrington, MA, United States
9.9Wonderful(27)
Free Wi-Fi
Pool
Pet friendly
€306+
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Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
10Wonderful(13)
Air conditioning
€351+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
9.4Wonderful(15)
Air conditioning
€354+
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Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.8Wonderful(17)
Free Wi-Fi
Pet friendly
Air conditioning
€387+
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Lakefront Berkshires Retreat with Deck, Dock and Boat! - Great Barrington
Lakefront Berkshires Retreat with Deck, Dock and Boat!
Great Barrington, MA, United States
7.2Good(21)
Free Wi-Fi
Pet friendly
€409+
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat! - Great Barrington - Bedroom
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Great Barrington, MA, United States
Free Wi-Fi
€433+
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Urban Peak Escape - Lenox - Kitchen
Urban Peak Escape
Lenox, MA, United States
10Wonderful(1)
Free Wi-Fi
Air conditioning
€435+
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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
10Wonderful(16)
Free Wi-Fi
Air conditioning
€447+
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Heart of Lenox!! - renovated downtown apartment - Lenox - Kitchen
Heart of Lenox!! - renovated downtown apartment
Lenox, MA, United States
9.8Wonderful(22)
Air conditioning
€578+
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A four-season forest cabin - Great Barrington - Living room
A four-season forest cabin
Great Barrington, MA, United States
9.5Wonderful(4)
€630+
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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
9.4Wonderful(23)
Parking
Free Wi-Fi
Pet friendly
Air conditioning
€684+
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
9.8Wonderful(40)
Free Wi-Fi
Air conditioning
€950+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
September
€218
€240
Cheapest month to stay with an average 35% drop in price.
Most expensive month to stay with an average 46% 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

  • 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, caravan parks, chalets, condos, cottages, houses, villas, cabins 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 17% 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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