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

The Berkshires Vacation Rentals

Find 25 available home rentals from 13 partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Accommodation types

    • Cabin
    • House
    • Farmhouse

  • Rating

    • 4.5+
    • 4+

  • 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

Top 15 Recommended vacation rentals in The Berkshires

Find your perfect vacation rental in The Berkshires from just $143 per night!

Cabin The Berkshires
Cabin ∙ 2 guests ∙ 1 bedroom

Cabin

The Berkshires, Sandisfield, Massachusetts, United States
This Monterey cottage features a kitchen, fireplace, and yard, making it the perfect retreat for you and your pet.
from $213
per night
Outstanding(73 ratings)
from $213
per night
View deal
House The Berkshires
House ∙ 14 guests ∙ 5 bedrooms

228 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This waterfront house rental in Monterey features a sauna, fireplace, jacuzzi, and lakeview balcony, perfect for family getaways.
from $1,113
per night
Outstanding(16 ratings)
from $1,113
per night
View deal
House The Berkshires
House ∙ 16 guests ∙ 6 bedrooms

415 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This Monterey house rental features a private pool, jacuzzi, and spacious yard, perfect for family gatherings of up to 16.
from $1,459
per night
Outstanding(42 ratings)
from $1,459
per night
View deal
Cabin The Berkshires
Cabin ∙ 5 guests ∙ 2 bedrooms

119 m² Cabin

The Berkshires, Sandisfield, Massachusetts, United States
This Monterey cottage offers a cozy yard, a fireplace, and a kitchen, perfect for a getaway with up to five guests and pets.
from $237
per night
Outstanding(89 ratings)
from $237
per night
View deal
House The Berkshires
House ∙ 16 guests ∙ 4 bedrooms

372 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This house rental in Otis features a balcony with lake and mountain views, a yard, and amenities for up to 16 guests.
from $782
per night
Outstanding(136 ratings)
from $782
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 3 bedrooms

214 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This house rental in Monterey features a lakeview, fireplace, jacuzzi, and a yard, perfect for family gatherings of up to 8.
from $320
per night
Outstanding(4 ratings)
from $320
per night
View deal
House The Berkshires
House ∙ 10 guests ∙ 4 bedrooms

288 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This Monterey house rental features a lakeview, fireplace, kitchen, and yard, accommodating up to 10 guests for a perfect getaway.
from $640
per night
Outstanding(112 ratings)
from $640
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 5 bedrooms

214 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This house rental in Monterey features a lakeview, yard, and a fireplace, perfect for family gatherings of up to 8.
from $544
per night
Outstanding(64 ratings)
from $544
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 3 bedrooms

153 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This house rental in Otis features a fireplace, kitchen, jacuzzi, and balcony with mountain views, perfect for family getaways.
from $339
per night
Outstanding(57 ratings)
from $339
per night
View deal
House The Berkshires
House ∙ 6 guests ∙ 3 bedrooms

223 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This lakeview house rental in Sandisfield features a fireplace, kitchen, yard, and waterfront access, perfect for six guests.
from $733
per night
Outstanding(30 ratings)
from $733
per night
View deal
House The Berkshires
House ∙ 9 guests ∙ 4 bedrooms

214 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This Monterey house rental features a fireplace, kitchen, yard, and jacuzzi, all with stunning mountain views for up to nine guests.
from $925
per night
Outstanding(53 ratings)
from $925
per night
View deal
Mobile home The Berkshires
Mobile home ∙ 8 guests ∙ 2 bedrooms

74 m² Mobile home

The Berkshires, Sandisfield, Massachusetts, United States
This mobile home in Otis features a kitchen, parking, and space for 8, perfect for your next memorable getaway.
from $226
per night
Outstanding(10 ratings)
from $226
per night
View deal
Cabin The Berkshires
Cabin ∙ 12 guests ∙ 5 bedrooms

Cabin

The Berkshires, Sandisfield, Massachusetts, United States
This Monterey cottage accommodates 12 with a kitchen, fireplace, and balcony, perfect for your next getaway with friends.
from $619
per night
from $619
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 4 bedrooms

353 m² House

The Berkshires, Sandisfield, Massachusetts, United States
This waterfront house in Monterey features a kitchen, sauna, jacuzzi, and stunning lake and mountain views, perfect for 12 guests.
$1,271 from $948
per night
Outstanding(79 ratings)
$1,271 from $948
per night
View deal
Cabin The Berkshires
Cabin ∙ 6 guests ∙ 3 bedrooms

83 m² Cabin

The Berkshires, Sandisfield, Massachusetts, United States
This cottage in Monterey features a fireplace, kitchen, and parking, accommodating up to six guests for an unforgettable getaway.
from $361
per night
Outstanding(15 ratings)
from $361
per night
View deal

Vacation rentals with a fireplace

House The Berkshires
from $856 per night
House ∙ 10 guests ∙ 4 bedrooms

93 m² House

5.0
Outstanding(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
House The Berkshires
from $1,424 per night
House ∙ 16 guests ∙ 6 bedrooms

415 m² House

4.8
Outstanding(42 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
House The Berkshires
from $606 per night
House ∙ 6 guests ∙ 3 bedrooms

House

5.0
Outstanding(42 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
See all offers

Apartments with a balcony or patio

Chalet The Berkshires
from $295 per night
Chalet ∙ 6 guests ∙ 2 bedrooms

125 m² Chalet

5.0
Outstanding(156 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House The Berkshires
from $732 per night
House ∙ 5 guests ∙ 3 bedrooms

149 m² House

4.5
Excellent(12 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House The Berkshires
from $331 per night
House ∙ 8 guests ∙ 3 bedrooms

232 m² House

4.9
Outstanding(80 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Vacation homes and cottages with a garden

Cabin The Berkshires
from $482 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cabin

5.0
Outstanding(4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
House The Berkshires
from $521 per night
House ∙ 10 guests ∙ 5 bedrooms

372 m² House

4.7
Excellent(50 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
Cabin The Berkshires
from $234 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

98 m² Cabin

4.8
Outstanding(61 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
See all offers

Budget-friendly Rentals in The Berkshires

Find Fantastic yet Inexpensive Rentals

Cabin The Berkshires
from $575 per night
Cabin ∙ 10 guests ∙ 3 bedrooms

Cabin

5.0
Outstanding(4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
Lodge The Berkshires
from $579 per night
Lodge ∙ 4 guests ∙ 1 bedroom

Lodge

The Berkshires, Sandisfield, Massachusetts, United States
View deal
Cabin The Berkshires
from $653 per night
Cabin ∙ 6 guests ∙ 4 bedrooms

Cabin

5.0
Outstanding(2 ratings)
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
from $756 per night
House ∙ 6 guests ∙ 2 bedrooms

212 m² House

5.0
Outstanding(23 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

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Popular Rental Amenities in The Berkshires

  • Pool (1)
  • Pet-friendly (8)
  • WiFi (25)
  • Air conditioning (22)
  • Kitchen (25)
  • TV (22)
  • Washing machine (23)
  • Parking (4)
  • Balcony/patio (15)
  • Dishwasher (22)
  • Grill (25)
  • Jacuzzi (5)

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 $534 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 (0).

Price and Availability Index in The Berkshires

Click on any bar to see price and availability information

Vacation Rental Price Information in The Berkshires

In the above graph, you will find information on average prices of the vacation rentals in The Berkshires. $763 is the highest price average in the next twelve months. In April (4/4 – 4/11), prices will hit an average low of $706 per night.

Rental availability information in The Berkshires

The graph shows the weekly availability rate in The Berkshiresfor the next twelve months. In a week of January (1/16 – 1/23), 97% of the vacation rentals are booked. It is easier to find a vacation rental in a week of February (2/7 – 2/14), as only 37% of the accommodations are booked.

Information about vacation rentals in The Berkshires

🏡 Vacation rentals available 25 rentals
🌙 Nightly prices starting at $143
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 8 homes
249 reviews
The Berkshires vacation rentals have an average rating of 4/5 on 249 reviews left by travelers.

Frequently Asked Questions

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

February 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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