The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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£54 - £940£940 - £1,824£1,824 - £2,710£2,710 - £3,594£3,594+ per night

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ApartmentCondoCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in The Berkshires

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Econo Lodge - Lee - Bedroom
Econo Lodge
Lee, MA, United States
5.7Fair(447)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£54+
Check availability
Berkshire Mountain Lodge - Pittsfield - Patio
Berkshire Mountain Lodge
Pittsfield, MA, United States
8.4Very Good(739)
Parking
Free Wi-Fi
Pool
Air conditioning
£97+
Check availability
Clover Hill Farm & Country Inn - Williamstown
Clover Hill Farm & Country Inn
Williamstown, MA, United States
9.6Wonderful(44)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£127+
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Cozy Renovated with 1 parking space - Pittsfield - Kitchen
Cozy Renovated with 1 parking space
Pittsfield, MA, United States
Air conditioning
£141+
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Cozy and quaint country cottage, walk to downtown Williamstown - Williamstown - Building
Cozy and quaint country cottage, walk to downtown Williamstown
Williamstown, MA, United States
9.6Wonderful(50)
£151+
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The Serendipity Spot - Great Barrington - Living room
The Serendipity Spot
Great Barrington, MA, United States
10Wonderful(1)
Air conditioning
£170+
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Water Street Apartments - Williamstown - Living room
Water Street Apartments
Williamstown, MA, United States
9.5Wonderful(22)
Free Wi-Fi
Air conditioning
£176+
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)
Parking
Free Wi-Fi
Air conditioning
£229+
Check availability
Stockbridge Home Walk to Town Beach! - Stockbridge - Living room
Stockbridge Home Walk to Town Beach!
Stockbridge, MA, United States
9.3Wonderful(11)
Free Wi-Fi
Air conditioning
£246+
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Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 - Great Barrington - Living room
Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9
Great Barrington, MA, United States
9.8Wonderful(16)
Air conditioning
£251+
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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
£352+
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Great Barrington Lakeside Getaway with Kayak and Grill - Great Barrington - Living room
Great Barrington Lakeside Getaway with Kayak and Grill
Great Barrington, MA, United States
8.8Very Good(8)
Free Wi-Fi
Air conditioning
£364+
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Great Barrington Lakeside Getaway w/ Kayak & Grill - Great Barrington - Living room
Great Barrington Lakeside Getaway w/ Kayak & Grill
Great Barrington, MA, United States
Free Wi-Fi
Air conditioning
£371+
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Lakefront Berkshires Retreat with Deck, Dock and Boat! - Great Barrington
Lakefront Berkshires Retreat with Deck, Dock and Boat!
Great Barrington, MA, United States
7.2Good(21)
Free Wi-Fi
Pet-friendly
£451+
Check availability
Lakefront Berkshires Retreat w/ Deck, Dock & Boat! - Great Barrington - Bedroom
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Great Barrington, MA, United States
£470+
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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)
Free Wi-Fi
£677+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
June
£182
£210
Cheapest month to stay with an average 27% drop in price.
Most expensive month to stay with an average 45% 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 £68. 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, cottages, houses, villas, cabins, campgrounds, lodges, condos, 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 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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