The Berkshires holiday rentals

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Recommended by KAYAK

Best The Berkshires holiday rentals

Walk to the Outfield of Lime Rock Park - Salisbury - Living room
Walk to the Outfield of Lime Rock Park
Salisbury, CT, United States
9.0Wonderful(18)
Apartment
Parking
Free Wi-Fi
Air conditioning
£236+
Check availability
Renovated Apartment on Main St. - Salisbury - Living room
Renovated Apartment on Main St.
Salisbury, CT, United States
7.3Good(3)
Apartment
Air conditioning
£271+
Check availability
Woodland Zen by AvantStay Modern Design Patio - Stockbridge - Living room
Woodland Zen by AvantStay Modern Design Patio
Stockbridge, MA, United States
10Wonderful(1)
House
Parking
Free Wi-Fi
Air conditioning
£416+
Check availability
Light-filled Carpenter's Cottage in Stockbridge - Stockbridge - Building
Light-filled Carpenter's Cottage in Stockbridge
Stockbridge, MA, United States
9.8Wonderful(10)
Cottage
Parking
Free Wi-Fi
Air conditioning
£204+
Check availability
Stockbridge Home Walk to Town Beach! - Stockbridge - Outdoor view
Stockbridge Home Walk to Town Beach!
Stockbridge, MA, United States
9.5Wonderful(14)
House
Free Wi-Fi
Air conditioning
£178+
Check availability
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) - Stockbridge - Living room
Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)
Stockbridge, MA, United States
8.8Very Good(14)
Condo
Free Wi-Fi
Air conditioning
£206+
Check availability
Econo Lodge - Lee - Bedroom
Econo Lodge
Lee, MA, United States
5.8Fair(450)
Lodge
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
£57+
Check availability
Summer in the Berkshires! - Stockbridge - Building
Summer in the Berkshires!
Stockbridge, MA, United States
10Wonderful(1)
Condo
Free Wi-Fi
Air conditioning
£364+
Check availability
Modern Cottage in the heart of the Berkshires with new exterior flex space! - Stockbridge - Living room
Modern Cottage in the heart of the Berkshires with new exterior flex space!
Stockbridge, MA, United States
9.7Wonderful(39)
House
Free Wi-Fi
Air conditioning
£522+
Check availability
Berkshire Mountain Lodge - Pittsfield - Lounge
Berkshire Mountain Lodge
Pittsfield, MA, United States
8.5Very Good(755)
Lodge
Parking
Free Wi-Fi
Pool
Air conditioning
£99+
Check availability
Too Good Aka 2 Goodrich St - Stockbridge - Living room
Too Good Aka 2 Goodrich St
Stockbridge, MA, United States
10Wonderful(24)
House
Free Wi-Fi
Air conditioning
£466+
Check availability
Berkshire's Best~On the Water~Mt. Views, Museums, Paddling, Hiking, Relaxing - North Adams - Bedroom
Berkshire's Best~On the Water~Mt. Views, Museums, Paddling, Hiking, Relaxing
North Adams, MA, United States
9.7Wonderful(27)
House
Free Wi-Fi
Air conditioning
£428+
Check availability
Stockbridge Village Cottage With Mountain View - Stockbridge - Dining room
Stockbridge Village Cottage With Mountain View
Stockbridge, MA, United States
9.8Wonderful(51)
House
Free Wi-Fi
Air conditioning
£438+
Check availability
Art House! Spacious Getaway By Mass Moca - North Adams - Living room
Art House! Spacious Getaway By Mass Moca
North Adams, MA, United States
9.6Wonderful(12)
House
Free Wi-Fi
Air conditioning
£363+
Check availability
Duplex In Historic Mill District Walkable To Williams & Spring St. - Williamstown - Dining room
Duplex In Historic Mill District Walkable To Williams & Spring St.
Williamstown, MA, United States
House
£77+
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
£113+
Check availability
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
June
£156
£161
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 106% 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 £62. Search here for similar prices

  • 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 £64 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, cottages, houses, villas, cabins, 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