The Berkshires holiday rentals

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Best The Berkshires holiday rentals

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£43 - £924£924 - £1,804£1,804 - £2,684£2,684 - £3,564£3,564+ per night

Property Types

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
5.8Fair(451)
Lodge
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£54+
Check availability
Berkshire Mountain Lodge - Pittsfield - Lounge
Berkshire Mountain Lodge
Pittsfield, MA, United States
8.4Very Good(752)
Lodge
Parking
Free Wi-Fi
Pool
Air conditioning
£103+
Check availability
Clover Hill Farm & Country Inn - Williamstown
Clover Hill Farm & Country Inn
Williamstown, MA, United States
9.6Wonderful(48)
Farm stay
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£126+
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(21)
Apartment
Air conditioning
£145+
Check availability
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(51)
House
£162+
Check availability
Water Street Apartments - Williamstown - Living room
Water Street Apartments
Williamstown, MA, United States
9.3Wonderful(22)
Apartment
Free Wi-Fi
Air conditioning
£174+
Check availability
Villa with Access to Various Amenities - Lee - Dining room
Villa with Access to Various Amenities
Lee, MA, United States
8.6Very Good(12)
Villa
Free Wi-Fi
Air conditioning
£179+
Check availability
Villa with Access to Amazing Amenities! - Lee - Building
Villa with Access to Amazing Amenities!
Lee, MA, United States
9.1Wonderful(82)
Villa
Free Wi-Fi
Air conditioning
£208+
Check availability
Spacious Villa with Access to Various Amenities! - Lee - Building
Spacious Villa with Access to Various Amenities!
Lee, MA, United States
9.7Wonderful(18)
Villa
Air conditioning
£233+
Check availability
Vacation Rental Home in the Berkshires! - Williamstown - Living room
Vacation Rental Home in the Berkshires!
Williamstown, MA, United States
9.6Wonderful(14)
Apartment
Free Wi-Fi
Air conditioning
£243+
Check availability
Stockbridge Home Walk to Town Beach! - Stockbridge - Living room
Stockbridge Home Walk to Town Beach!
Stockbridge, MA, United States
9.4Wonderful(12)
House
Free Wi-Fi
Air conditioning
£252+
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
£253+
Check availability
Bungalow in the Berkshires - Lee - Living room
Bungalow in the Berkshires
Lee, MA, United States
10Wonderful(1)
House
Air conditioning
£318+
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
£349+
Check availability
A roomy remodeled retreat close to MassMoCA - North Adams - Kitchen
A roomy remodeled retreat close to MassMoCA
North Adams, MA, United States
9.9Wonderful(22)
House
Free Wi-Fi
Air conditioning
£357+
Check availability
Lee Manor - Lee - Bedroom
Lee Manor
Lee, MA, United States
House
Parking
Free Wi-Fi
Pet-friendly
£565+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

October
June
£171
£194
Cheapest month to stay with an average 27% drop in price.
Most expensive month to stay with an average 46% 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 £59. 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, lodges, condos, campgrounds, 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