The Berkshires Vacation Rentals - Wimdu base64Hash The Berkshires Vacation Rentals - Wimdu

The Berkshires Vacation Rentals

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Choose from 24 vacation rentals and homes for your trip!

Best-rated vacation rentals in The Berkshires

Discover vacation rentals with top-notch guest ratings

House The Berkshires
-25%
$991
from $742 per night
House ∙ 12 guests ∙ 4 bedrooms

Fully equipped nice house with yard, sauna & hot tub | Lake view | Good for workation

4.8
Outstanding(84 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cabin The Berkshires
from $254 per night
Cabin ∙ 9 guests ∙ 4 bedrooms

Fully equipped nice cabin with yard, terrace & barbecue | Pets allowed

4.8
Outstanding(67 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
from $668 per night
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly vacation home with terrace, garden & hot tub | Mountain view

5.0
Outstanding(53 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Pet-friendly rentals in The Berkshires

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House The Berkshires
from $414 per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with hot tub, pool & patio

The Berkshires, Sandisfield, Massachusetts, United States
Pet-friendly
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Farmhouse The Berkshires
from $264 per night
Farmhouse ∙ 6 guests ∙ 2 bedrooms

Farm with yard & barbeque | Perfect for remote work

5.0
Outstanding(6 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Pet-friendly
View deal
House The Berkshires
from $254 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with BBQ & terrace | Lake view

The Berkshires, Sandisfield, Massachusetts, United States
Pet-friendly
View deal
See all pet-friendly offers

Best vacation rental offers in The Berkshires

Cabin The Berkshires
from $991 per night
Cabin ∙ 12 guests ∙ 4 bedrooms

Fully equipped cottage with barbeque, terrace & yard | Good for workation

4.8
Outstanding(84 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
Cabin The Berkshires
from $277 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with patio & barbeque

5.0
Outstanding(12 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
from $443 per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation home with barbeque, garden & terrace | Lake view | Good for workation

4.8
Outstanding(64 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cabin The Berkshires
from $172 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Fully equipped cottage with barbecue, patio & garden | Nature view | Suitable for remote work | Dogs allowed

4.8
Outstanding(89 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $274 per night
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly house with yard, patio & jacuzzi | Mountain view

4.9
Outstanding(63 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
from $610 per night
House ∙ 8 guests ∙ 5 bedrooms

Child-friendly lovely vacation home with barbecue, yard & terrace | Lake view | Dogs allowed

5.0
Outstanding(45 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $588 per night
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly ample vacation home with garden & barbeque | Lake view | Pets allowed

5.0
Outstanding(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
from $529 per night
House ∙ 5 guests ∙ 3 bedrooms

House with barbeque, hot tub & patio | Lake view | Suitable for remote work

4.5
Excellent(12 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cabin The Berkshires
from $577 per night
Cabin ∙ 6 guests ∙ 4 bedrooms

Cottage with 4 rooms for 6 persons

5.0
Outstanding(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $521 per night
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly charming vacation home with barbeque, garden & terrace | Pets allowed

5.0
Outstanding(6 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $420 per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented pleasant house with barbecue, terrace & garden | Lake view | Perfect for remote work | Dogs allowed

4.0
Very good(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $486 per night
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly spacious house with terrace, hot tub & barbeque | Lake view

5.0
Outstanding(23 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $707 per night
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly vacation home with sauna, terrace & garden | Mountain view | Good for workation

4.8
Outstanding(84 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
Cabin The Berkshires
from $272 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with barbeque | Good for workation

The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $361 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbecue & patio | Nature view

5.0
Outstanding(10 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
Mobile home The Berkshires
from $222 per night
Mobile home ∙ 8 guests ∙ 3 bedrooms

Nice mobile home with grill & patio

4.8
Outstanding(10 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
Cabin The Berkshires
from $446 per night
Cabin ∙ 12 guests ∙ 5 bedrooms

Cottage with barbecue

The Berkshires, Sandisfield, Massachusetts, United States
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Show all 3970 apartments in The Berkshires

Price and Availability Index in The Berkshires

Click on any bar to see price and availability information

Vacation Rental Price Information in The Berkshires

We analyzed data from the last 12 months and built the graph above to show you accommodation prices in The Berkshires. Vacation rental prices in The Berkshires are at their highest in July and reach on average $518 per night. In contrast, May and the period of 5/30 – 6/6 are the most affordable in the year, with vacation rental prices at $497 per night.

Rental availability information in The Berkshires

Here, you can see how busy The Berkshires will be at different times of year. The busiest time of year in The Berkshires is April. The week with the highest availability is in June (6/13 – 6/20) - 69% of the vacation rentals are still available.

And we love our apartments

Fully equipped cottage with barbeque, terrace & yard | Good for workation
Cottage with patio & barbeque
Vacation home with barbeque, garden & terrace | Lake view | Good for workation
Fully equipped cottage with barbecue, patio & garden | Nature view | Suitable for remote work | Dogs allowed
Family-friendly house with yard, patio & jacuzzi | Mountain view
Show all 3970 apartments in The Berkshires

Features of The Berkshires vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Internet, Pool and Pets allowed
🌙 Minimum price starting at $122
🐾 Pet friendly vacation homes 9 rentals

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Beautiful regions near to consider for next trip

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