The Berkshires holiday rentals

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Best The Berkshires holiday rentals

Charming Winter Ski Rental in Great Barrington, MA - Housatonic - Living room
Charming Winter Ski Rental in Great Barrington, MA
Housatonic, MA, United States
10Wonderful(1)
House
Free Wi-Fi
Air conditioning
€242+
Check availability
Gem of the Berkshires. Mountain View. Short walk to lake & downtown. - Great Barrington - Balcony
Gem of the Berkshires. Mountain View. Short walk to lake & downtown.
Great Barrington, MA, United States
10Wonderful(5)
House
Free Wi-Fi
Air conditioning
€840+
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
€1,074+
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Cozy escape in the trees of the Berkshires - Great Barrington - Living room
Cozy escape in the trees of the Berkshires
Great Barrington, MA, United States
10Wonderful(4)
House
Free Wi-Fi
€786+
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(86)
Cottage
Free Wi-Fi
Air conditioning
€262+
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Restored 1881 Farm House - Lenox - Kitchen
Restored 1881 Farm House
Lenox, MA, United States
9.8Wonderful(22)
House
Free Wi-Fi
Pet friendly
Air conditioning
€389+
Check availability
Walk to Dining: Downtown Lenox Guest House! - Lenox - Patio
Walk to Dining: Downtown Lenox Guest House!
Lenox, MA, United States
9.6Wonderful(15)
Cottage
Free Wi-Fi
Air conditioning
€322+
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Main Street Delight 1bedroom - Lenox - Living room
Main Street Delight 1bedroom
Lenox, MA, United States
9.9Wonderful(24)
Apartment
Air conditioning
€309+
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Farmhouse-Loft -48 Main Street, Lenox, Ma - Lenox - Living room
Farmhouse-Loft -48 Main Street, Lenox, Ma
Lenox, MA, United States
10Wonderful(12)
Apartment
Air conditioning
€607+
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Heart Of Lenox Walk To Town Cozy Cottage! - Lenox - Living room
Heart Of Lenox Walk To Town Cozy Cottage!
Lenox, MA, United States
10Wonderful(47)
House
Free Wi-Fi
Air conditioning
€389+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA, United States
9.5Wonderful(16)
Apartment
Air conditioning
€273+
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Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA, United States
10Wonderful(15)
Apartment
Air conditioning
€279+
Check availability
Chic Modern Farmhouse 1 mile to Downtown Lenox - Lenox - Living room
Chic Modern Farmhouse 1 mile to Downtown Lenox
Lenox, MA, United States
10Wonderful(11)
House
Free Wi-Fi
Air conditioning
€1,165+
Check availability
Urban Peak Escape - Lenox - Kitchen
Urban Peak Escape
Lenox, MA, United States
9.0Wonderful(1)
Apartment
Free Wi-Fi
Air conditioning
€308+
Check availability
Colonial House, w/Yard,7min walk to Downtown Lenox - Lenox - Living room
Colonial House, w/Yard,7min walk to Downtown Lenox
Lenox, MA, United States
10Wonderful(3)
House
Free Wi-Fi
Air conditioning
€303+
Check availability
Walk to Dining Downtown Lenox Guest House! - Lenox
Walk to Dining Downtown Lenox Guest House!
Lenox, MA, United States
9.6Wonderful(9)
House
Free Wi-Fi
Air conditioning
€310+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
September
€164
€232
Cheapest month to stay with an average 24% drop in price.
Most expensive month to stay with an average 44% 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 5% 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