The Berkshires Vacation Rentals

Compare 1,943 available properties from 15 providers
The Berkshires
Anytime
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Bed & Breakfast
House
Apartment
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
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Best Vacation Home Deals The Berkshires

House Winsted
-25%
Mar. 6 - Mar. 13
House ∙ 12 guests ∙ 5 bedrooms
Winsted, Winchester, Connecticut, United States
from $541 $721
Vrbo
5.0/5.0
"Excellent"
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Book a welcoming property for as little as $108 per night by searching among the 15 options featured in The Berkshires. Using HomeToGo's search feature you can instantaneously search and compare the prices of each listed property to find the best deal and save up to 25%.

Recommended Vacation Rentals The Berkshires

Find your perfect vacation rental The Berkshires: from $108 per night

Condo Hancock 8
-30%
May 29 - Jun. 5
Condo ∙ 8 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts, United States
from $160 $229
Resort Rental Pros
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Bed & Breakfast Norfolk 2
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Norfolk, Litchfield County, Connecticut, United States
from $382
GlobalTripper
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Bed & Breakfast Pittsfield 4
-21%
May 1 - May 8
Bed & Breakfast ∙ 4 guests ∙ 1 bedroom
Pittsfield, Berkshire County, Massachusetts, United States
from $389 $489
Agoda
4.6/5.0
"Outstanding"
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Bed & Breakfast West Stockbridge 2
Free cancellation
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
West Stockbridge, Berkshire County, Massachusetts, United States
from $333
Agoda
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Bed & Breakfast Norfolk 2
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Norfolk, Litchfield County, Connecticut, United States
from $295
HomeToGo
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Bed & Breakfast Norfolk 2
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Norfolk, Litchfield County, Connecticut, United States
from $349
HomeToGo
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Bed & Breakfast Norfolk 2
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Norfolk, Litchfield County, Connecticut, United States
from $310
HomeToGo
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Bed & Breakfast Norfolk 2
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Norfolk, Litchfield County, Connecticut, United States
from $224
HomeToGo
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Bed & Breakfast Norfolk 2
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Norfolk, Litchfield County, Connecticut, United States
from $282
HomeToGo
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Vacation rentals with Wi-Fi

Apartment Internet Lenox
Internet
Apartment ∙ 2 guests ∙ 1 bedroom
Lenox, Berkshire County, Massachusetts, United States
from $254
Vrbo
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 $255
Vrbo
4.8/5.0
"Excellent"
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House Internet Morris
Internet
House ∙ 7 guests ∙ 3 bedrooms
Morris, Litchfield County, Connecticut, United States
from $565
Vrbo
4.6/5.0
"Outstanding"
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Vacation rentals and apartments with air conditioning

Apartment Aircondition Lenox
Aircondition
Apartment ∙ 4 guests ∙ 1 bedroom
Lenox, Berkshire County, Massachusetts, United States
from $254
Vrbo
5.0/5.0
"Excellent"
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House Aircondition Hillsdale
Aircondition
House ∙ 6 guests ∙ 4 bedrooms
Hillsdale, Columbia County, New York, United States
from $534
Vrbo
4.8/5.0
"Excellent"
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House Aircondition Lenox
Aircondition
House ∙ 5 guests ∙ 3 bedrooms
Lenox, Berkshire County, Massachusetts, United States
from $435
Vrbo
5.0/5.0
"Excellent"
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Apartments and vacation rentals with a kitchen

House Kitchen South Lee
-21%
Apr. 3 - Apr. 10
Kitchen
House ∙ 6 guests ∙ 2 bedrooms
South Lee, Lee, Massachusetts, United States
from $336 $427
Vrbo
4.7/5.0
"Outstanding"
View deal
House Kitchen New Milford
Kitchen
House ∙ 6 guests ∙ 3 bedrooms
New Milford, Litchfield County, Connecticut, United States
from $334
Vrbo
5.0/5.0
"Excellent"
View deal
House Kitchen Lee
Kitchen
House ∙ 6 guests ∙ 4 bedrooms
Lee, Berkshire County, Massachusetts, United States
from $489
Vrbo
5.0/5.0
"Excellent"
View deal
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Popular Rental Amenities The Berkshires

  • Internet (1,151)
  • Parking (1,106)
  • No smoking (1,106)
  • Air conditioning (1,040)
  • TV (909)
  • Yard (668)
  • Wheelchair access (618)
  • Microwave (581)
  • No pets (562)
  • Pet allowed (522)
  • Pool (520)
  • Balcony/Patio (401)

Finding a vacation rental with a pool shouldn't be too hard The Berkshires. Nearly half of the vacation rentals have one. Additionally, more Hotel rooms have pools than any other type of property. They are a great choice if you go in a group of 3, as that is the number of people they can usually accommodate. Among these rentals, 9 of them are located within 2 kilometres of water.

The Weather The Berkshires

max.
Min.

-7°
15 days 15
max.
Min.

-7°
15 days 15
max.
Min.

-2°
13 days 13
max.
Min.
16°
13 days 13
max.
Min.
23°
10°
14 days 14
max.
Min.
27°
14°
13 days 13
max.
Min.
30°
18°
14 days 14
max.
Min.
29°
16°
11 days 11
max.
Min.
25°
12°
11 days 11
max.
Min.
18°
12 days 12
max.
Min.
11°
10 days 10
max.
Min.

-2°
16 days 16
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for The Berkshires. On average, the warmest month is July. On the contrary, the coolest month is January. Bring your umbrella in December, the rainiest month of the year!

We compare more than 40,000 providers, including:

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

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