The Berkshires holiday rentals

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Recommended by KAYAK

Best The Berkshires holiday rentals

Most recommended holiday rentals in The Berkshires

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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
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
Great Barrington apartment, Short walk to downtown - Great Barrington
Great Barrington apartment, Short walk to downtown
Great Barrington, MA, United States
Air conditioning
Romantic Berkshires Cottage - Stunning Views, Pool - Great Barrington - Dining room
Romantic Berkshires Cottage - Stunning Views, Pool
Great Barrington, MA, United States
Free Wi-Fi
Pool
Pet friendly
Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
Air conditioning
Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
Air conditioning
Perfect Great Barrington Spot, Nature, and Views! - Great Barrington
Perfect Great Barrington Spot, Nature, and Views!
Great Barrington, MA, United States
Air conditioning
Restored 1881 Farm House - Lenox - Kitchen
Free Wi-Fi
Pet friendly
Air conditioning
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town - Great Barrington - Dining room
Parking
Free Wi-Fi
Pet friendly
Air conditioning
5 Star Casual Elegance For 5 Star Guests - Lenox - Outdoor view
Free Wi-Fi
Air conditioning
Sunsets On Blue Hill, Newly Renovated Farmhouse - Great Barrington - Living room
Sunsets On Blue Hill, Newly Renovated Farmhouse
Great Barrington, MA, United States
Air conditioning
A four-season forest cabin - Great Barrington - Living room
A four-season forest cabin
Great Barrington, MA, United States
The Great Escape Ski Cottage W/Hot Tub @ Great Barrington - Great Barrington - Living room
Free Wi-Fi
Air conditioning
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Good to know

Low season

September

High season

December

Average price (weeknight)

€981

Average price (weekend night)

€264
Cheapest month to stay with an average 59% drop in price.
Most expensive month to stay with an average 592% 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, 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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