The Berkshires Vacation Rentals

Compare 3,459 available properties from 20 providers
The Berkshires
Anytime
2 guests
Save up to 49%

Best Vacation Home Deals The Berkshires

-49%
e.g. 3/16 - 3/23
House ∙ 7 guests ∙ 4 bedrooms
Richmond, Berkshire County, Massachusetts, United States
from $208 $409
VRBO
5.0
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-36%
e.g. 5/4 - 5/11
House ∙ 5 guests ∙ 2 bedrooms
West Stockbridge, Berkshire County, Massachusetts, United States
from $414 $646
VRBO
4.9
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-20%
e.g. 3/16 - 3/23
House ∙ 8 guests ∙ 3 bedrooms
Glendale, Stockbridge, Massachusetts, United States
from $424 $531
VRBO
5.0
View deal

3,461 great accommodations from 20 different vacation rental websites, such as VRBO or TripAdvisor, are currently available in The Berkshires. HomeToGo instantly highlights the best offers by comparing all of the available vacation homes in The Berkshires from 20 different providers.

Recommended Vacation Rentals The Berkshires

Find your perfect vacation rental The Berkshires: from $26 per night

Apartment ∙ 2 guests ∙ 1 bedroom
Danbury, Fairfield County, Connecticut, United States
from $130
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
New Fairfield, Fairfield County, Connecticut, United States
from $298
VRBO
5.0
View deal
House ∙ 6 guests ∙ 3 bedrooms
Salisbury, Litchfield County, Connecticut, United States
from $181
VRBO
4.8
View deal
House ∙ 6 guests ∙ 2 bedrooms
Taconic, Salisbury, Connecticut, United States
from $340
VRBO
4.7
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Apartment ∙ 4 guests ∙ 1 bedroom
Housatonic, Great Barrington, Massachusetts, United States
from $143
VRBO
4.9
View deal
House ∙ 4 guests ∙ 1 bedroom
East Otis, Otis, Massachusetts, United States
from $134
VRBO
4.8
View deal
House ∙ 4 guests ∙ 2 bedrooms
Hinsdale, Berkshire County, Massachusetts, United States
from $141
VRBO
4.6
View deal
House ∙ 4 guests ∙ 2 bedrooms
New Fairfield, Fairfield County, Connecticut, United States
from $421
VRBO
5.0
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House ∙ 4 guests ∙ 2 bedrooms
Savoy, Berkshire County, Massachusetts, United States
from $263
VRBO
4.9
View deal
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Vacation rentals with a fireplace

Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Peru, Berkshire County, Massachusetts, United States
from $214
VRBO
4.9
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Fireplace
House ∙ 8 guests ∙ 5 bedrooms
Monterey, Berkshire County, Massachusetts, United States
from $458
VRBO
4.4
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Lenox, Berkshire County, Massachusetts, United States
from $510
VRBO
4.8
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $506
VRBO
5.0
View deal
Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Danbury, Fairfield County, Connecticut, United States
from $587
VRBO
4.7
View deal
Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Washington, Litchfield County, Connecticut, United States
from $467
VRBO
5.0
View deal
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Vacation homes with fishing spots nearby

Fishing
Apartment ∙ 4 guests ∙ 1 bedroom
Lanesborough, Berkshire County, Massachusetts, United States
from $65
VRBO
4.8
View deal
Fishing
House ∙ 4 guests ∙ 1 bedroom
Pittsfield, Berkshire County, Massachusetts, United States
from $265
VRBO
4.8
View deal
Fishing
House ∙ 6 guests ∙ 4 bedrooms
New Marlborough, Berkshire County, Massachusetts, United States
from $289
VRBO
4.8
View deal
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Popular Rental Amenities The Berkshires

  • Internet (3,006)
  • Kitchen (2,880)
  • TV (2,592)
  • Washer (2,236)
  • AC (2,203)
  • Fireplace (1,677)
  • Microwave (1,591)
  • Yard (1,342)
  • Grill (1,282)
  • Dishwasher (1,244)
  • Pet allowed (1,067)
  • No smoking (1,065)

Price and Availability Index in The Berkshires

Vacation Rental Price Information The Berkshires

This graph displays average prices of the vacation rentals and holiday apartments located The Berkshires. The most expensive week of the next 12 months is in June (6/22 - 6/29), where prices hit an average of $430 a night. Opt for a getaway in March (3/7 - 3/14) for optimal savings when heading to The Berkshires.

Rental Availability Information The Berkshires

Check how busy The Berkshires is with our availability graph. The most challenging week to find a rental in the next twelve months is in July (7/13 - 7/20). It will be easy to find a rental that suits you in a week of September (9/28 - 10/5), as 85% of the rentals are still available.

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 600 providers, including:

Booking.com Vacation Rentals The Berkshires Novasol Vacation Rentals The Berkshires TripAdvisor Vacation Rentals The Berkshires Airbnb Vacation Rentals The Berkshires Inter Chalet Vacation Rentals The Berkshires HomeAway 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