The Berkshires holiday rentals

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Useful Info
Recommended by KAYAK

Best The Berkshires holiday rentals

Most recommended holiday rentals in The Berkshires

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Beautiful 1920's Colonial 20 Minutes from Tanglewood - Great Barrington
Beautiful 1920's Colonial 20 Minutes from Tanglewood
Great Barrington, MA, United States
Pet-friendly
Air conditioning
Berkshire Mountain Cottage: in the Heart of the Berkshires - Great Barrington
Pet-friendly
Air conditioning
Nestled minutes from Main Street, Great Barrington - Great Barrington
Nestled minutes from Main Street, Great Barrington
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
Perfect Great Barrington Spot, Nature, and Views! - Great Barrington
Perfect Great Barrington Spot, Nature, and Views!
Great Barrington, MA, United States
Air conditioning
Renovated house on the Hill. Walk everywhere! - Great Barrington
Renovated house on the Hill. Walk everywhere!
Great Barrington, MA, United States
Air conditioning
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town - Great Barrington - Dining room
Parking
Free Wi-Fi
Pet-friendly
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
The Great Escape Ski Cottage W/Hot Tub @ Great Barrington - Great Barrington - Living room
Free Wi-Fi
Air conditioning
Moose Lodge by Avantstay Luxe Berkshires Escape - Great Barrington - Living room
Moose Lodge by Avantstay Luxe Berkshires Escape
Great Barrington, MA, United States
Free Wi-Fi
Air conditioning
Useful Info

Good to know

Low season

June

High season

December

Average price (weeknight)

R113 675

Average price (weekend night)

R16 491
Cheapest month to stay with an average 86% drop in price.
Most expensive month to stay with an average 221% 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 apartments, cabins, campgrounds, cottages and houses.

  • 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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