The Berkshires vacation rentals

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Best The Berkshires vacation rentals

Most recommended vacation rentals in The Berkshires

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Vacation Village in the Berkshires - Hancock - Pool
Vacation Village in the Berkshires
8.3 Very good
625 ﷼+
625 ﷼+
Free Wi-Fi
Pool
Air Conditioning
Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak - Hancock - Living room
Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak
9.5 Wonderful
723 ﷼+
723 ﷼+
Parking
Free Wi-Fi
Pool
Air Conditioning
Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy - Hancock - Living room
Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy - Hancock - Living room
Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy
8.6 Very good
723 ﷼+
723 ﷼+
Parking
Free Wi-Fi
Pool
Air Conditioning
Great Barrington Lakeside Getaway with Kayak and Grill - Great Barrington - Living room
Great Barrington Lakeside Getaway with Kayak and Grill - Great Barrington - Living room
Great Barrington Lakeside Getaway with Kayak and Grill
8.5 Very good
1,619 ﷼+
1,619 ﷼+
Free Wi-Fi
Air Conditioning
Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off - Lanesborough - Living room
Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off - Lanesborough - Living room
Gorgeous 1st FL Mtn View Jiminy Suite Sleeps 4 Ski On Off
8.8 Very good
682 ﷼+
682 ﷼+
Parking
Free Wi-Fi
Pool
Air Conditioning
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 - Bedroom
Cozy Great Barrington Home about 1 Mi to Ski Resort!
9.8 Wonderful
2,047 ﷼+
2,047 ﷼+
Free Wi-Fi
Air Conditioning
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining - Great Barrington - Patio
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining - Great Barrington - Patio
Half Moon by AvantStay 4BR Cabin w Large Deck Yard w Patio Outdoor Dining
9.1 Wonderful
2,755 ﷼+
2,755 ﷼+
Free Wi-Fi
Pet friendly
Air Conditioning
Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk - Hancock - Living room
Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk - Hancock - Living room
Wow-New Ski Onoff Suite By Pool Sleeps 4 Jiminy Pk
9 Wonderful
671 ﷼+
671 ﷼+
Parking
Free Wi-Fi
Pool
Air Conditioning
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 ! - Great Barrington - Property amenity
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 ! - Great Barrington - Property amenity
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !
9.7 Wonderful
2,159 ﷼+
2,159 ﷼+
Pool
Air Conditioning
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town - Great Barrington - Living room
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town - Great Barrington - Living room
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town
2,635 ﷼+
2,635 ﷼+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor - Hancock - Building
1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor - Hancock - Building
1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor
8 Very good
705 ﷼+
705 ﷼+
Parking
Free Wi-Fi
Pool
Air Conditioning
Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 - Hancock - Bedroom
Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 - Hancock - Bedroom
Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4
9.4 Wonderful
832 ﷼+
832 ﷼+
Parking
Free Wi-Fi
Pool
Air Conditioning
Jurassic Dino Suite Jiminy-Must See Sleeps 4 - Hancock - Bedroom
Jurassic Dino Suite Jiminy-Must See Sleeps 4 - Hancock - Bedroom
Jurassic Dino Suite Jiminy-Must See Sleeps 4
9.3 Wonderful
615 ﷼+
615 ﷼+
Free Wi-Fi
Pool
Air Conditioning
Ski-In/Ski-Out at Jiminy Peak in the Country Inn - Hancock - Bedroom
Ski-In/Ski-Out at Jiminy Peak in the Country Inn - Hancock - Bedroom
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
1,136 ﷼+
1,136 ﷼+
Free Wi-Fi
Air Conditioning
2 Bed Berkshire Getaway minutes to Jiminy Peak Ski - Hancock
2 Bed Berkshire Getaway minutes to Jiminy Peak Ski - Hancock
2 Bed Berkshire Getaway minutes to Jiminy Peak Ski
9.8 Wonderful
712 ﷼+
712 ﷼+
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
Downtown GB apartment walk to shops and restaurants - Great Barrington
Downtown GB apartment walk to shops and restaurants - Great Barrington
Downtown GB apartment walk to shops and restaurants
1,185 ﷼+
1,185 ﷼+
Air Conditioning
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KAYAK’s insights for vacation rentals in The Berkshires

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in The Berkshires with confidence.

Which month has the cheapest vacation rental rates in The Berkshires?

Vacation rentals are cheapest in The Berkshires in May, with average rates of 143 ﷼. In comparison, October is the most expensive month, with prices at 314 ﷼.

What is the cheapest day of the week to book a vacation rental in The Berkshires?

Thursday offers the lowest rates in The Berkshires, with an average nightly price of 121 ﷼. The highest prices are found on Tuesday, with average rates at 233 ﷼.
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Good to know

Low season

April

High season

December

Average price (weeknight)

4,077 ﷼

Average price (weekend night)

1,621 ﷼
Cheapest month to stay with an average 62% drop in price.
Most expensive month to stay with an average 515% 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 vacation home in The Berkshires

  • How much is a vacation rental in The Berkshires for tonight?

    In the last 72 hours, users have found The Berkshires vacation rentals for tonight for as low as 578 ﷼. Search here for similar prices

  • What types of vacation rentals are available in The Berkshires?

    There are loads of different property types that you can make your vacation home in The Berkshires. You’ll find apartments, cabins, campgrounds, cottages, houses, agritourism and condos.

  • Are there any pet-friendly vacation rentals in The Berkshires?

    There are a number of dog and pet-friendly The Berkshires vacation rentals, with around 21% 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 vacation home.

Everything you need to know for your stay in The Berkshires

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