The Berkshires vacation rentals

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Latest The Berkshires vacation rental deals

MOST POPULARLenox
Vacation homes from $121
Pittsfield
Vacation homes from $106
Lee
Vacation homes from $84

Best The Berkshires vacation rentals

Berkshires Getaway Less Than 1 Mi Skiing and Hiking! - Charlemont - Bedroom
Berkshires Getaway Less Than 1 Mi Skiing and Hiking!
Charlemont, MA
9.9Wonderful(11)
Apartment
Free Wi-Fi
$648+
Check availability
Relaxing Mountaintop Retreat in the Northern Berkshires - Hawley - Living room
Relaxing Mountaintop Retreat in the Northern Berkshires
Hawley, MA
10Wonderful(1)
House
$582+
Check availability
Beautiful 2-bedroom apartment in New Lebanon - New Lebanon
Beautiful 2-bedroom apartment in New Lebanon
New Lebanon, NY
8.0Very good(1)
Apartment
$190+
Check availability
Vacation Village in the Berkshires - Hancock - Pool
Vacation Village in the Berkshires
Hancock, MA
8.3Very good(1251)
Apartment
Free Wi-Fi
Pool
$124+
Check availability
Bear Creek Cabin - Charlemont - Building
Bear Creek Cabin
Charlemont, MA
9.8Wonderful(20)
Cabin
Free Wi-Fi
$599+
Check availability
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! - Charlemont - Living room
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
Charlemont, MA
Cottage
Free Wi-Fi
$346+
Check availability
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location - Lanesborough - Bedroom
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Lanesborough, MA
9.6Wonderful(16)
House
Free Wi-Fi
$436+
Check availability
Ashley Falls Home w/ Fire Pit: Hike & Ski! - Ashley Falls - Living room
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Ashley Falls, MA
9.5Wonderful(4)
House
$505+
Check availability
Relax or be active! The choice is yours in this pet-friendly family home. - Norfolk - Living room
Relax or be active! The choice is yours in this pet-friendly family home.
Norfolk, CT
9.7Wonderful(16)
House
Free Wi-Fi
$260+
Check availability
20 minutes to Jiminy Peak and Bousquet Mountain - New Lebanon - Lounge
20 minutes to Jiminy Peak and Bousquet Mountain
New Lebanon, NY
10Wonderful(3)
Villa
$1,718+
Check availability
Elterwater--Your lakefront oasis, a Berkshire getaway. Long term discount. - Sheffield - Living room
Elterwater--Your lakefront oasis, a Berkshire getaway. Long term discount.
Sheffield, MA
9.7Wonderful(54)
House
Free Wi-Fi
$368+
Check availability
Berkshires Getaway 1 Mi Skiing & Hiking! - Charlemont - Bedroom
Berkshires Getaway 1 Mi Skiing & Hiking!
Charlemont, MA
10Wonderful(1)
Condo
$675+
Check availability
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions - Sheffield - Kitchen
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
House
$742+
Check availability
Cheerful 3-bedroom cottage with woodstove - Sheffield - Patio
Cheerful 3-bedroom cottage with woodstove
Sheffield, MA
9.8Wonderful(34)
House
Free Wi-Fi
$451+
Check availability
Fickle Fox Farm. Daffodils are popping their heads up, summer is coming! - Canaan - Bedroom
Fickle Fox Farm. Daffodils are popping their heads up, summer is coming!
Canaan, CT
10Wonderful(17)
House
Free Wi-Fi
$444+
Check availability
Great Family Cabin in the woods on a lake. - Norfolk - Living room
Great Family Cabin in the woods on a lake.
Norfolk, CT
10Wonderful(3)
Cabin
Free Wi-Fi
$361+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
June
$178
$217
Cheapest month to stay with an average 32% drop in price.
Most expensive month to stay with an average 36% 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 $98. Search here for similar prices

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

    The average price for a weekly The Berkshires vacation rental found by KAYAK users in the last 2 weeks is $1,619.

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

    The average price for a monthly The Berkshires vacation rental found by KAYAK users in the last 2 weeks is $6,938.

  • 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 cottages, houses, lodges, agritourism, apartments, cabins, condos, luxury tents, caravans, chalets, villas, campgrounds, farm stays, castles and homestays.

  • What are some of the most-loved vacation rentals available in The Berkshires?

    There are many types of properties available for The Berkshires vacation rentals. If you’re looking for something special, vacation rentals most loved by KAYAK users are Vacation Village in the Berkshires and Berkshire Mountain Lodge.

  • 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 5% 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

Complete your trip to The Berkshires

Vacations in The Berkshires