Vacation rentals in The Berkshires - HomeToGo base64Hash Vacation rentals in The Berkshires - HomeToGo

Vacation rentals in The Berkshires

Find 36 available house rentals from 16 partners
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Top 15 Recommended vacation rentals in The Berkshires

Find your perfect vacation rental in The Berkshires from just $115 per night!

House The Berkshires
House ∙ 10 guests ∙ 4 bedrooms

House with yard, patio & BBQ | Lake view

The Berkshires, Sandisfield, Massachusetts, United States
from $286
per night
Outstanding(99 ratings)
from $286
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 5 bedrooms

Children-friendly house with terrace, garden & barbecue | City view | Dogs allowed

The Berkshires, Sandisfield, Massachusetts, United States
from $652
per night
Outstanding(27 ratings)
from $652
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 5 bedrooms

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

The Berkshires, Sandisfield, Massachusetts, United States
from $1,030
per night
Excellent(12 ratings)
from $1,030
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 4 bedrooms

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

The Berkshires, Sandisfield, Massachusetts, United States
from $304
per night
Outstanding(46 ratings)
from $304
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly vacation home with barbecue, yard & patio | Lake view | Suitable for remote work | Pets are welcome

The Berkshires, Sandisfield, Massachusetts, United States
from $356
per night
Very good(2 ratings)
from $356
per night
View deal
House The Berkshires
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with yard & terrace | Nature view

The Berkshires, Sandisfield, Massachusetts, United States
from $660
per night
Outstanding(27 ratings)
from $660
per night
View deal
House The Berkshires
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with grill & pool

The Berkshires, Sandisfield, Massachusetts, United States
from $414
per night
from $414
per night
View deal
Cottage The Berkshires
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage with patio & barbeque

The Berkshires, Sandisfield, Massachusetts, United States
from $263
per night
Outstanding(6 ratings)
from $263
per night
View deal
Farmhouse The Berkshires
Farmhouse ∙ 8 guests ∙ 4 bedrooms

Farm with 4 rooms for 8 persons

The Berkshires, Sandisfield, Massachusetts, United States
from $499
per night
from $499
per night
View deal
Mobile home The Berkshires
Mobile home ∙ 8 guests ∙ 3 bedrooms

Nice mobile home with grill

The Berkshires, Sandisfield, Massachusetts, United States
from $235
per night
Outstanding(8 ratings)
from $235
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 4 bedrooms

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

The Berkshires, Sandisfield, Massachusetts, United States
from $738
per night
from $738
per night
View deal
Cabin The Berkshires
Cabin ∙ 6 guests ∙ 3 bedrooms

Child-friendly cabin with BBQ | Pets allowed

The Berkshires, Sandisfield, Massachusetts, United States
from $291
per night
Excellent
from $291
per night
View deal
House The Berkshires
House ∙ 9 guests ∙ 4 bedrooms

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

The Berkshires, Sandisfield, Massachusetts, United States
from $874
per night
Outstanding(51 ratings)
from $874
per night
View deal
House The Berkshires
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with grill, yard & hot tub

The Berkshires, Sandisfield, Massachusetts, United States
from $715
per night
Excellent(4 ratings)
from $715
per night
View deal
Cottage The Berkshires
Cottage ∙ 12 guests ∙ 4 bedrooms

Fully equipped cottage with barbeque & sauna | Good for workation

The Berkshires, Sandisfield, Massachusetts, United States
from $1,064
per night
from $1,064
per night
View deal

Vacation houses with Balconies or Patios

House  The Berkshires
from $528
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with jacuzzi & BBQ | Lake view

5.0
Outstanding(1 rating)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House  The Berkshires
from $329
per night
House ∙ 6 guests ∙ 4 bedrooms

Family-oriented ample house with yard, patio & barbecue

4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House  The Berkshires
from $538
per night
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped pleasant vacation home with yard, barbecue & patio | Dogs allowed

5.0
Outstanding(37 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Vacation homes and rentals with a yard

House  The Berkshires
from $300
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented big house with terrace, grill & garden

4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
House  The Berkshires
from $164
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully equipped pleasant vacation home with BBQ, yard & terrace | Nature view

5.0
Outstanding(27 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
Cottage  The Berkshires
from $234
per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Children-friendly cottage with yard & terrace | Lake view

4.7
Excellent(45 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
See all offers

Vacation rentals with a balcony

House  The Berkshires
from $333
per night
House ∙ 6 guests ∙ 3 bedrooms

Spacious vacation home with barbeque & garden | Lake view | Good for workation | Dogs allowed

4.7
Excellent(3 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony
View deal
House  The Berkshires
from $449
per night
House ∙ 16 guests ∙ 4 bedrooms

Family-friendly house with garden, BBQ & patio | Lake view | Pets allowed

5.0
Outstanding(135 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony
View deal
House  The Berkshires
from $430
per night
House ∙ 10 guests ∙ 5 bedrooms

House with barbecue, terrace & yard | Nature view

4.7
Excellent(48 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony
View deal
See all offers

Budget-friendly Vacation Rentals in The Berkshires

Find Fantastic yet Inexpensive Offers

House The Berkshires
from $359
per night
House ∙ 10 guests ∙ 4 bedrooms

House with grill

The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $563
per night
House ∙ 10 guests ∙ 4 bedrooms

Children-friendly ample vacation home with yard, BBQ & patio | Lake view

5.0
Outstanding(114 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
Cottage The Berkshires
from $240
per night
Cottage ∙ 6 guests ∙ 4 bedrooms

Cottage with terrace & grill | Nature view | Suitable for remote work

5.0
Outstanding(44 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

Top-Rated Rentals and Accommodations in The Berkshires

Book Vacation Rental Offers with the Highest User Rating

House The Berkshires
from $613
per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation home with barbecue & terrace | Lake view

4.8
Outstanding(18 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $1,064
per night
House ∙ 16 guests ∙ 9 bedrooms

Child-friendly house with yard, BBQ & terrace | Perfect for remote work

4.5
Excellent(6 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $314
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with barbeque | Dogs allowed

5.0
Outstanding(4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

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Popular Rental Amenities in The Berkshires

  • Pet-friendly (11)
  • Pool (1)
  • WiFi (36)
  • Air conditioning (29)
  • TV (29)
  • Fireplace (31)
  • Hot tub (7)
  • Kitchen (36)
  • Balcony/patio (12)
  • Grill (28)
  • Fishing (8)
  • Washing machine (29)

If you want to bring your pet, you can effortlessly find a pet-friendly accommodation in The Berkshires with HomeToGo. Cabin are the most pet-friendly type of property in The Berkshires. In addition, a night in a pet-friendly property there is, on average, $547. There's no need to search for accommodations away outside of the city, as a few of the vacation rentals are pet-friendly have a central location (less than 2 miles from the city center).

Price and Availability Index in The Berkshires

Click on any bar to see price and availability information

Vacation Rental Price Information in The Berkshires

The graph shows average prices of rentals in The Berkshires for the upcoming twelve months. The most expensive dates to travel to The Berkshires are in August (8/16 – 8/23). You can find the most affordable prices on accommodations in June. Prices during that period are typically $394 per night on average.

Rental availability information in The Berkshires

Find out how busy the upcoming months are going to be in The Berkshires using our availability graph. The week with the highest booking rate is in April (4/25 – 5/2). Only 11% of the rentals are still available. The week with the most available rentals is in June (6/7 – 6/14), with 54% of the vacation rentals available.

See beautiful Northeastern mountains with Berkshires vacation rentals

The Berkshires are a haven for nature lovers. Most of your days will be filled with outdoor activities such as hiking, biking, kayaking, canoeing, horseback riding or just sitting out on the deck with a coffee in hand. A Berkshire vacation homes include lakefront summer houses, sprawling estates with swimming pools, waterfront cottages and farmhouses built for large family gatherings.

What are the best activities for families in The Berkshires?

Fun family activities

The Catamount Aerial Adventure Park is fun for the whole family. The park features 12 self-guided courses and more than 50 zip lines for all ability levels.

At the Museum of Animation, Special Effects and Art, kids create their own animation movie and see special effects from movies, such as Spiderman and Predator.

The Berkshire Museum features an aquarium, a miniature exhibit, rocks and minerals display, science of color exhibit, native American art collection and natural science area.

Where are the unique attractions in The Berkshires?

Getting out and about

Travel back in time along the Berkshire 18th Century Trail. Visitors can tour six magnificently preserved historic homes, each displaying original furnishings and artifacts.

The 15-acre Berkshire Botanical Garden is home to more than 3,000 species and varieties, with an emphasis on regionally indigenous plants.

Berkshire Canoe Tours offers guided canoe trip on the Housatonic River. The 1.5- to 2-hour guided tours take visitors to see the sights and sounds of local wildlife.

Information about vacation rentals in The Berkshires

🏡 Vacation rentals available 36 rentals
💳 Possible discounts up to 45%
🌙 Nightly prices starting at $115
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 11 homes
498,523 reviews
The Berkshires vacation rentals have an average rating of 4.4/5 on 498,523 reviews left by travelers.

Frequently Asked Questions

What is the average price per night for a vacation rental in The Berkshires?

The price of a night's stay in The Berkshires starts at $115. Average prices for house rentals are $649 per night. Cottages in The Berkshires cost $541 per night on average.

How many vacation homes are available for booking in The Berkshires?

There are 36 rentals from 16 different providers in The Berkshires.

What amenities are most popular for vacation rentals in The Berkshires?

If you're looking to book a vacation rental in The Berkshires, the most popular amenities are: Pets allowed, Pool and Internet.

How many vacation rentals with a pool are in The Berkshires?

Choose from 1 vacation rentals available in The Berkshires.

Are dogs allowed in vacation homes in The Berkshires?

Finding a rental in The Berkshires that allows pets is possible, with 11 pet-friendly available.

What's the best month to travel to The Berkshires?

If choosing a vacation rental in The Berkshires, keep in mind that rainy season is usually in December or January, with November often being the driest.

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