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
Hancock, MA, United States
8.3Very good(1269)
Free Wi-Fi
Pool
Air Conditioning
694 ﷼+
Check availability
Unique - 1br Country Condo @ Jiminy Peak - Hancock - Living room
Unique - 1br Country Condo @ Jiminy Peak
Hancock, MA, United States
Free Wi-Fi
Pool
Air Conditioning
1,106 ﷼+
Check availability
Elegant Mountain View Retreat By Evergreen Home - Williamstown - Living room
Elegant Mountain View Retreat By Evergreen Home
Williamstown, MA, United States
Free Wi-Fi
Air Conditioning
2,474 ﷼+
Check availability
Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak - Hancock - Building
Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak
Hancock, MA, United States
10Wonderful(6)
Parking
Free Wi-Fi
Air Conditioning
3,085 ﷼+
Check availability
Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy - Hancock - Living room
Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy
Hancock, MA, United States
8.6Very good(24)
Parking
Free Wi-Fi
Pool
Air Conditioning
678 ﷼+
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
9.8Wonderful(14)
Free Wi-Fi
Air Conditioning
1,735 ﷼+
Check availability
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
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
1,450 ﷼+
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
Free Wi-Fi
Air Conditioning
4,520 ﷼+
Check availability
Sunsets On Blue Hill, Newly Renovated Farmhouse - Great Barrington - Living room
Sunsets On Blue Hill, Newly Renovated Farmhouse
Great Barrington, MA, United States
Air Conditioning
3,950 ﷼+
Check availability
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, MA, United States
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
3,238 ﷼+
Check availability
Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter - Lanesborough
Wyndham Bentley Brook at Jiminy Peak in the Berkshires -Play in Summer or Winter
Lanesborough, MA, United States
Pool
Air Conditioning
686 ﷼+
Check availability
Bentley Brook Accomodations Ski-In Ski-out @ Jiminy Peak 2 Bedroom Rental - Lanesborough
Bentley Brook Accomodations Ski-In Ski-out @ Jiminy Peak 2 Bedroom Rental
Lanesborough, MA, United States
Pool
Air Conditioning
1,874 ﷼+
Check availability
Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer - Lanesborough
Wyndham Bentley Brook at Jiminy Peak - Play in the Winter or the Summer
Lanesborough, MA, United States
Pool
Air Conditioning
558 ﷼+
Check availability
The entire Stephentown Hotel. 28 person occupancy - Hancock
The entire Stephentown Hotel. 28 person occupancy
Hancock, MA, United States
10Wonderful(1)
Parking
Free Wi-Fi
Pet friendly
Air Conditioning
4,910 ﷼+
Check availability
Bentley Brook Ski-In Ski-Out Rentals @ Jiminy Peak Mtn - Lanesborough
Bentley Brook Ski-In Ski-Out Rentals @ Jiminy Peak Mtn
Lanesborough, MA, United States
Pool
Air Conditioning
1,158 ﷼+
Check availability
Nestled minutes from Main Street, Great Barrington - Great Barrington
Nestled minutes from Main Street, Great Barrington
Great Barrington, MA, United States
Air Conditioning
1,132 ﷼+
Check availability
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Property Types

ApartmentCondoCottageHouse

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

April

High season

December

Average price (weeknight)

5,082 ﷼

Average price (weekend night)

1,677 ﷼
Cheapest month to stay with an average 78% drop in price.
Most expensive month to stay with an average 403% 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 544 ﷼. 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 20% 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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