The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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€62 - €1,052€1,052 - €2,041€2,041 - €3,030€3,030 - €4,019€4,019+ per night

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Most recommended holiday rentals in The Berkshires

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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)
Free Wi-Fi
Air conditioning
€269+
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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)
Parking
Free Wi-Fi
Air conditioning
€274+
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Renovated Apartment on Main St. - Salisbury - Living room
Renovated Apartment on Main St.
Salisbury, CT, United States
Air conditioning
€297+
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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(29)
Free Wi-Fi
€299+
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Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.8Wonderful(20)
Free Wi-Fi
Pet friendly
Air conditioning
€394+
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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)
Free Wi-Fi
Air conditioning
€412+
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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
€456+
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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
Air conditioning
€468+
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Private Country Retreat in Lovely Lakeville CT - Lakeville - Living room
Private Country Retreat in Lovely Lakeville CT
Lakeville, CT, United States
Air conditioning
€479+
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Cottage in the woods - Salisbury - Patio
Cottage in the woods
Salisbury, CT, United States
Free Wi-Fi
Air conditioning
€484+
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Spacious 5-bedroom house with Pool on 2 lovely acres - Salisbury
Spacious 5-bedroom house with Pool on 2 lovely acres
Salisbury, CT, United States
10Wonderful(3)
Air conditioning
€510+
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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
Air conditioning
€546+
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Beautiful 4-Season Rental Directly On Twin Lakes - Salisbury - Bedroom
Beautiful 4-Season Rental Directly On Twin Lakes
Salisbury, CT, United States
Air conditioning
€569+
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The Country Retreat House - Lakeville - Living room
The Country Retreat House
Lakeville, CT, United States
10Wonderful(5)
Free Wi-Fi
Air conditioning
€606+
Check availability
Gem of the Berkshires. Mountain View. Short walk to lake & downtown. - Great Barrington - Patio
Gem of the Berkshires. Mountain View. Short walk to lake & downtown.
Great Barrington, MA, United States
10Wonderful(3)
Free Wi-Fi
Air conditioning
€931+
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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(41)
Free Wi-Fi
Air conditioning
€1,185+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
September
€213
€269
Cheapest month to stay with an average 37% drop in price.
Most expensive month to stay with an average 40% 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 this weekend?

    In the last 72 hours, users have found The Berkshires holiday rentals for this weekend for as little as €393 per night. 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, chalets, cottages, houses, villas, cabins, campgrounds 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

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