The Berkshires Vacation Rentals

Compare 1,245 available properties from 17 providers
The Berkshires
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
Save up to 37%

Best Vacation Home Deals The Berkshires

House Copake
-37%
Dec. 5 - Dec. 12
House ∙ 6 guests ∙ 2 bedrooms
Copake, Columbia County, New York, United States
from $343 $541
Squared Living
4.0/5.0
"Very good"
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House Copake
-37%
Dec. 5 - Dec. 12
House ∙ 8 guests ∙ 3 bedrooms
Copake, Columbia County, New York, United States
from $319 $506
Squared Living
5.0/5.0
"Excellent"
View deal

1,245 great accommodations from 17 different vacation rental websites, such as Homelidays or stayz, are currently available in The Berkshires. HomeToGo instantly highlights the best offers by comparing all of the available vacation homes in The Berkshires from 17 different providers.

Recommended Vacation Rentals The Berkshires

Find your perfect vacation rental The Berkshires: from $102 per night

Condo Hancock 8
-41%
Apr. 24 - May 1
Condo ∙ 8 guests ∙ 1 bedroom
Hancock, Berkshire County, Massachusetts, United States
from $128 $217
Resort Rental Pros
4.7/5.0
"Outstanding"
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House Cummington 6
House ∙ 6 guests ∙ 3 bedrooms
Cummington, Hampshire County, Massachusetts, United States
from $331
Vrbo
4.6/5.0
"Outstanding"
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House Hinsdale 4
House ∙ 4 guests ∙ 2 bedrooms
Hinsdale, Berkshire County, Massachusetts, United States
from $187
Vrbo
4.8/5.0
"Excellent"
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House Lanesborough 6
House ∙ 6 guests ∙ 3 bedrooms
Lanesborough, Berkshire County, Massachusetts, United States
from $192
Vrbo
4.9/5.0
"Excellent"
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House Becket 4
House ∙ 4 guests ∙ 2 bedrooms
Becket, Berkshire County, Massachusetts, United States
from $269
Vrbo
5.0/5.0
"Excellent"
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House Becket 5
House ∙ 5 guests ∙ 1 bedroom
Becket, Berkshire County, Massachusetts, United States
from $140
Vrbo
4.9/5.0
"Excellent"
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House Sherwood Forest 4
House ∙ 4 guests ∙ 2 bedrooms
Sherwood Forest, Becket, Massachusetts, United States
from $223
Vrbo
4.6/5.0
"Outstanding"
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House Sharon 6
House ∙ 6 guests ∙ 3 bedrooms
Sharon, Litchfield County, Connecticut, United States
from $429
Vrbo
4.6/5.0
"Outstanding"
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House Savoy 4
House ∙ 4 guests ∙ 2 bedrooms
Savoy, Berkshire County, Massachusetts, United States
from $285
Vrbo
4.9/5.0
"Excellent"
View deal
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Vacation rentals with a fireplace

House Fireplace Hillsdale
Fireplace
House ∙ 3 guests ∙ 1 bedroom
Hillsdale, Columbia County, New York, United States
from $234
Vrbo
5.0/5.0
"Excellent"
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House Fireplace Hillsdale
Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Hillsdale, Columbia County, New York, United States
from $229
Vrbo
4.7/5.0
"Outstanding"
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House Fireplace Stockbridge
Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Stockbridge, Berkshire County, Massachusetts, United States
from $483
Vrbo
5.0/5.0
"Excellent"
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Vacation rentals with Wi-Fi

House Internet Copake
-42%
Dec. 5 - Dec. 12
Internet
House ∙ 8 guests ∙ 3 bedrooms
Copake, Columbia County, New York, United States
from $309 $530
Squared Living
5.0/5.0
"Excellent"
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House Internet Monterey
Internet
House ∙ 5 guests ∙ 2 bedrooms
Monterey, Berkshire County, Massachusetts, United States
from $262
Vrbo
4.8/5.0
"Excellent"
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House Internet Copake
-18%
Jan. 9 - Jan. 16
Internet
House ∙ 5 guests ∙ 3 bedrooms
Copake, Columbia County, New York, United States
from $325 $397
Vrbo
4.8/5.0
"Excellent"
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Vacation rentals and apartments with air conditioning

House Aircondition Tolland
Aircondition
House ∙ 5 guests ∙ 2 bedrooms
Tolland, Hampden County, Massachusetts, United States
from $230
Vrbo
4.9/5.0
"Excellent"
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House Aircondition Hillsdale
Aircondition
House ∙ 4 guests ∙ 1 bedroom
Hillsdale, Columbia County, New York, United States
from $188
Vrbo
5.0/5.0
"Excellent"
View deal
House Aircondition Copake Falls
Aircondition
House ∙ 4 guests ∙ 2 bedrooms
Copake Falls, Copake, New York, United States
from $220
Vrbo
4.9/5.0
"Excellent"
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Popular Rental Amenities The Berkshires

  • Parking (773)
  • No smoking (766)
  • Internet (748)
  • Kitchen (655)
  • TV (491)
  • Air conditioning (488)
  • No pets (475)
  • Grill (470)
  • Microwave (450)
  • Washer (443)
  • Yard (413)
  • Dishwasher (357)

The Weather The Berkshires


-7°

-7°

-2°
16°
23°
10°
27°
14°
30°
18°
29°
16°
25°
12°
18°
11°

-2°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. In the next 6 months, July will have higher average temperatures. On the contrary, the coolest month is January. The rainiest month is December while the driest month is November.

We compare more than 2,000 providers, including:

Booking.com Vacation Rentals The Berkshires TripAdvisor Vacation Rentals The Berkshires Vrbo Vacation Rentals The Berkshires Airbnb Vacation Rentals The Berkshires Novasol Vacation Rentals The Berkshires Inter Chalet Vacation Rentals The Berkshires EveryStay Vacation Rentals The Berkshires Interhome Vacation Rentals The Berkshires 9flats.com Vacation Rentals The Berkshires HouseTrip Vacation Rentals The Berkshires Belvilla Vacation Rentals The Berkshires Sykes Cottages Vacation Rentals The Berkshires Homestay.com Vacation Rentals The Berkshires Ski Planet Vacation Rentals The Berkshires Only-apartments Vacation Rentals The Berkshires James Villa Holidays Vacation Rentals The Berkshires
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