The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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€62 - €1,056€1,056 - €2,049€2,049 - €3,041€3,041 - €4,034€4,034+ per night

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Most recommended holiday rentals in The Berkshires

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Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
10Wonderful(13)
Apartment
Air conditioning
€260+
Check availability
Walk to the Outfield of Lime Rock Park - Salisbury - Living room
Walk to the Outfield of Lime Rock Park
Salisbury, CT, United States
9.1Wonderful(17)
Apartment
Parking
Free Wi-Fi
Air conditioning
€280+
Check availability
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, Majestic Views - Salisbury - Living room
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, Majestic Views
Salisbury, CT, United States
9.6Wonderful(85)
Cottage
Free Wi-Fi
Air conditioning
€295+
Check availability
Serene Salisbury Rental Home on 26 Acres with Deck! - Salisbury
Serene Salisbury Rental Home on 26 Acres with Deck!
Salisbury, CT, United States
10Wonderful(3)
House
Free Wi-Fi
Air conditioning
€349+
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Serene Salisbury Rental Home on 26 Acres w/ Deck! - Salisbury - Living room
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Salisbury, CT, United States
9.7Wonderful(8)
Cottage
Free Wi-Fi
Air conditioning
€382+
Check availability
Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.8Wonderful(21)
House
Free Wi-Fi
Pet friendly
Air conditioning
€395+
Check availability
Renovated Apartment on Main St. - Salisbury - Living room
Renovated Apartment on Main St.
Salisbury, CT, United States
6.0Okay(2)
Apartment
Air conditioning
€436+
Check availability
Beautiful Twin Lakes Rental - Weekly Or Seasonal Term Available - Salisbury - Dining room
Beautiful Twin Lakes Rental - Weekly Or Seasonal Term Available
Salisbury, CT, United States
Cottage
Air conditioning
€468+
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Heart of Lenox!! - renovated downtown apartment - Lenox - Kitchen
Heart of Lenox!! - renovated downtown apartment
Lenox, MA, United States
9.8Wonderful(25)
Apartment
Air conditioning
€503+
Check availability
Cottage in the woods - Salisbury - Balcony
Cottage in the woods
Salisbury, CT, United States
9.0Wonderful(1)
House
Free Wi-Fi
Air conditioning
€538+
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6 Br 'camp' House On Twin Lakes - Epic Historic Property - Salisbury - Living room
6 Br 'camp' House On Twin Lakes - Epic Historic Property
Salisbury, CT, United States
House
Air conditioning
€549+
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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
10Wonderful(1)
House
Air conditioning
€594+
Check availability
Curated Contemporary for lakes, forest & ski hills - Salisbury - Lounge
Curated Contemporary for lakes, forest & ski hills
Salisbury, CT, United States
10Wonderful(5)
House
Free Wi-Fi
Air conditioning
€597+
Check availability
The Country Retreat House - Lakeville - Living room
The Country Retreat House
Lakeville, CT, United States
10Wonderful(5)
House
Free Wi-Fi
Air conditioning
€609+
Check availability
5-bedroom house with gunite pool on 2 acres. Hot tub and wood burning fire place - Salisbury - Kitchen
5-bedroom house with gunite pool on 2 acres. Hot tub and wood burning fire place
Salisbury, CT, United States
10Wonderful(4)
House
Free Wi-Fi
Air conditioning
€621+
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(42)
House
Free Wi-Fi
Air conditioning
€1,085+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
November
€186
€234
Cheapest month to stay with an average 37% drop in price.
Most expensive month to stay with an average 43% 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, cottages, houses, villas, cabins and lodges.

  • 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 4% 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