The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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£52 - £898£898 - £1,742£1,742 - £2,588£2,588 - £3,433£3,433+ per night

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Most recommended holiday rentals in The Berkshires

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Econo Lodge - Lee - Bedroom
Econo Lodge
Lee, MA, United States
5.6Fair(447)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£52+
Check availability
Clover Hill Farm & Country Inn - Williamstown
Clover Hill Farm & Country Inn
Williamstown, MA, United States
9.6Wonderful(38)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£121+
Check availability
Amazing 2-bedroom apartment sunny and quiet in Great Barrington - Great Barrington - Bedroom
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Great Barrington, MA, United States
9.5Wonderful(20)
Free Wi-Fi
Air conditioning
£159+
Check availability
Elegant 19th Century New England Newly Renovated 1br Vacation Rental - Lee - Patio
Elegant 19th Century New England Newly Renovated 1br Vacation Rental
Lee, MA, United States
9.6Wonderful(19)
Pet-friendly
Air conditioning
£160+
Check availability
Piebald Mountain Pet Friendly Tents, Petersburg, New York - Williamstown
Piebald Mountain Pet Friendly Tents, Petersburg, New York
Williamstown, MA, United States
Pet-friendly
Air conditioning
£194+
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Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown - North Adams - Living room
Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown
North Adams, MA, United States
9.7Wonderful(8)
Free Wi-Fi
Air conditioning
£195+
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Large Duplex Near Massmoca, Mcla (21) - North Adams - Building
Large Duplex Near Massmoca, Mcla (21)
North Adams, MA, United States
10Wonderful(1)
£219+
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Stockbridge Home Walk to Town Beach! - Stockbridge - Living room
Stockbridge Home Walk to Town Beach!
Stockbridge, MA, United States
9.3Wonderful(10)
Free Wi-Fi
Air conditioning
£234+
Check availability
1 Mi to Dtwn Beautiful Home in Williamstown! - Williamstown - Living room
1 Mi to Dtwn Beautiful Home in Williamstown!
Williamstown, MA, United States
Free Wi-Fi
Air conditioning
£388+
Check availability
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
£388+
Check availability
Best of the Berkshires with Mt. Views, Museums, Paddling, Hiking & On the Water! - North Adams - Bedroom
Best of the Berkshires with Mt. Views, Museums, Paddling, Hiking & On the Water!
North Adams, MA, United States
9.6Wonderful(25)
Free Wi-Fi
Air conditioning
£422+
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Autumn Leaves Of Scarlet And Gold With Evenings Of Warm Drinks - Lenox
Autumn Leaves Of Scarlet And Gold With Evenings Of Warm Drinks
Lenox, MA, United States
Air conditioning
£433+
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Too Good Aka 2 Goodrich St - Stockbridge - Living room
Too Good Aka 2 Goodrich St
Stockbridge, MA, United States
10Wonderful(21)
Free Wi-Fi
Air conditioning
£459+
Check availability
Secluded 19th century Farmhouse with mountain views - North Adams - Building
Secluded 19th century Farmhouse with mountain views
North Adams, MA, United States
10Wonderful(1)
£548+
Check availability
11 acre mid-century estate, newly renovated, seasonally available pool. - Williamstown - Living room
11 acre mid-century estate, newly renovated, seasonally available pool.
Williamstown, MA, United States
10Wonderful(15)
Free Wi-Fi
Pool
Air conditioning
£778+
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(40)
Free Wi-Fi
Air conditioning
£824+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

November
June
£156
£216
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 48% 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 tonight?

    In the last 72 hours, users have found The Berkshires holiday rentals for tonight for as little as £70. 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, caravan parks, chalets, condos, cottages, houses, villas, cabins, campgrounds, lodges, farm stays, luxury tents and homestays.

  • What are some of the most-loved holiday rentals available in The Berkshires?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Econo Lodge.

  • 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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