The Berkshires Vacation Rentals - HomeToGo base64Hash The Berkshires Vacation Rentals - HomeToGo

The Berkshires Vacation Rentals

Find 31 available home rentals from 16 partners
Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Cabin
    • House
    • Farmhouse

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • Air conditioning
    • Kitchen
    • TV
    • Washing machine
    • Parking
    • Balcony/patio
    • Dishwasher
    • Jacuzzi
    • Fireplace
    • Yard
    • Microwave
    • Sauna
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Recommended vacation rentals in The Berkshires

Find your perfect vacation rental in The Berkshires from just $164 per night!

Cottage The Berkshires
Cottage ∙ 12 guests ∙ 5 bedrooms

Cottage

The Berkshires, Sandisfield, Massachusetts, United States
from $568
per night
from $568
per night
View deal
Cottage The Berkshires
Cottage ∙ 12 guests ∙ 4 bedrooms

Cottage

The Berkshires, Sandisfield, Massachusetts, United States
from $1,067
per night
from $1,067
per night
View deal
House The Berkshires
House ∙ 10 guests ∙ 4 bedrooms

183 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $376
per night
Outstanding(100 ratings)
from $376
per night
View deal
House The Berkshires
House ∙ 10 guests ∙ 4 bedrooms

184 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $487
per night
from $487
per night
View deal
Cottage The Berkshires
-22%
May 3 - May 10
Free cancellation
Cottage ∙ 6 guests ∙ 3 bedrooms

83 m² Cottage

The Berkshires, Sandisfield, Massachusetts, United States
$498$390
per night
Outstanding(1 rating)
$498$390
per night
View deal
House The Berkshires
-50%
Mar 1 - Mar 8
Free cancellation
House ∙ 16 guests ∙ 6 bedrooms

415 m² House

The Berkshires, Sandisfield, Massachusetts, United States
$3,100$1,535
per night
$3,100$1,535
per night
View deal
House The Berkshires
Jan 17 - Jan 24
House ∙ 6 guests ∙ 4 bedrooms

212 m² House

The Berkshires, Sandisfield, Massachusetts, United States
$845
per night
Outstanding(15 ratings)
$845
per night
View deal
House The Berkshires
Jan 25 - Feb 1
House ∙ 8 guests ∙ 4 bedrooms

167 m² House

The Berkshires, Sandisfield, Massachusetts, United States
$281
per night
Outstanding(2 ratings)
$281
per night
View deal
Cabin The Berkshires
Cabin ∙ 10 guests ∙ 7 bedrooms

184 m² Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $340
per night
Outstanding(100 ratings)
from $340
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 4 bedrooms

153 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $358
per night
Outstanding(44 ratings)
from $358
per night
View deal
House The Berkshires
House ∙ 9 guests ∙ 4 bedrooms

214 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $1,074
per night
Outstanding(51 ratings)
from $1,074
per night
View deal
House The Berkshires
House ∙ 6 guests ∙ 3 bedrooms

223 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $869
per night
Outstanding(31 ratings)
from $869
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 5 bedrooms

House

The Berkshires, Sandisfield, Massachusetts, United States
from $809
per night
Outstanding(27 ratings)
from $809
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 5 bedrooms

353 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $1,117
per night
Very good(9 ratings)
from $1,117
per night
View deal
Cottage The Berkshires
Cottage ∙ 6 guests ∙ 3 bedrooms

84 m² Cottage

The Berkshires, Sandisfield, Massachusetts, United States
from $342
per night
Outstanding(6 ratings)
from $342
per night
View deal

Vacation rentals with a fireplace

House The Berkshires
from $791 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(111 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
Cottage The Berkshires
from $218 per night
Cottage ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(52 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
Chalet The Berkshires
from $454 per night
Chalet ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding(32 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
See all offers

Apartments with a balcony or patio

House The Berkshires
from $256 per night
House ∙ 6 guests ∙ 4 bedrooms
4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
Chalet The Berkshires
from $324 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(115 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House The Berkshires
from $207 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding(27 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

Cottage The Berkshires
from $575 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
House The Berkshires
from $633 per night
House ∙ 16 guests ∙ 4 bedrooms
5.0
Outstanding(134 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
House The Berkshires
from $642 per night
House ∙ 8 guests ∙ 5 bedrooms
4.8
Outstanding(58 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
See all offers

Best Vacation Home Deals in The Berkshires

Save up to 21%

House The Berkshires
Jan 18 - Jan 25
-21%
$602
$473 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

Compare and find the ideal vacation rental from $164 per night by searching among the 31 options featured in The Berkshires. HomeToGo instantaneously sorts all of these vacation rentals so you can save up to 23%!

Budget-friendly Rentals in The Berkshires

Find Fantastic yet Inexpensive Rentals

House The Berkshires
from $422 per night
House ∙ 8 guests ∙ 4 bedrooms
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $479 per night
House ∙ 10 guests ∙ 4 bedrooms
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $1,333 per night
House ∙ 9 guests ∙ 4 bedrooms
The Berkshires, Sandisfield, Massachusetts, United States
View deal

Top-Rated Offers and Accommodations in The Berkshires

Book Vacation Rentals with the Highest User Rating

House The Berkshires
Jan 11 - Jan 18
$815 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

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Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in The Berkshires

  • Pool (2)
  • Pet-friendly (10)
  • WiFi (31)
  • Air conditioning (26)
  • Kitchen (31)
  • TV (27)
  • Washing machine (21)
  • Parking (2)
  • Balcony/patio (10)
  • Dishwasher (20)
  • Grill (21)
  • Jacuzzi (6)

If you want to bring your pet, you can easily find a pet-friendly vacation home in The Berkshires. Also, pet-friendly vacation homes in The Berkshires have an average price of $771 per night. You can also find different vacation home options if you would like to rent near the city center, as a few of the pet-friendly accommodations are less than 2 mile away from the center of the city (10).

Information about vacation rentals in The Berkshires

🏡 Vacation rentals available 31 rentals
💳 Possible discounts up to 23%
🌙 Nightly prices starting at $164
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 10 homes
🏊 Vacation rentals with pools 2 homes
485,260 reviews
The Berkshires vacation rentals have an average rating of 4.4/5 on 485,260 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in The Berkshires?

March has the highest availability of House rental in The Berkshires, so you can expect a lot of vacation rentals available, even for last-minute bookings.

What are the most popular vacation home amenities in The Berkshires?

The most popular amenities for rentals in The Berkshires include vacation homes with Pool, Pets allowed, or Internet.

Are there pet-friendly vacation rentals in The Berkshires?

If you're travelling with a dog, over 32% of vacation rentals in The Berkshires are pet-friendly.

What's the best month to book a vacation rental in The Berkshires?

When booking a vacation rental in The Berkshires, remember that the rainiest months are usually December and January, with November often being the sunniest.

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