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

The Berkshires Vacation Rentals

Find 33 available house rentals from 18 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in The Berkshires

Find your perfect vacation rental in The Berkshires from just $114 per night!

House The Berkshires
-60%
Feb 14 - Feb 21
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home with Grill & Patio | Lake View

The Berkshires, Sandisfield, Massachusetts, United States
$608$265
per night
Outstanding(18 ratings)
$608$265
per night
View deal
House The Berkshires
Jun 13 - Jun 20
House ∙ 10 guests ∙ 4 bedrooms

Child-Friendly Lovely House with Garden, Barbecue & Patio | Lake View

The Berkshires, Sandisfield, Massachusetts, United States
$601
per night
Outstanding(112 ratings)
$601
per night
View deal
House The Berkshires
Nov 8 - Nov 15
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home with Yard, Patio & Grill | Lake View | Suitable for Remote Work

The Berkshires, Sandisfield, Massachusetts, United States
$523
per night
Outstanding(59 ratings)
$523
per night
View deal
House The Berkshires
Jun 28 - Jul 5
House ∙ 8 guests ∙ 3 bedrooms

Child-Friendly Ample Vacation Home with Garden, Barbeque & Patio | Nature View

The Berkshires, Sandisfield, Massachusetts, United States
$256
per night
Outstanding(74 ratings)
$256
per night
View deal
Cottage The Berkshires
Jun 21 - Jun 28
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage with Yard, Patio & BBQ | Nature View

The Berkshires, Sandisfield, Massachusetts, United States
$181
per night
Outstanding(52 ratings)
$181
per night
View deal
House The Berkshires
Apr 12 - Apr 19
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home with Patio, Yard & Barbecue | Lake View | Good for Workation

The Berkshires, Sandisfield, Massachusetts, United States
$688
per night
Excellent(12 ratings)
$688
per night
View deal
Cottage The Berkshires
Apr 9 - Apr 16
Cottage ∙ 6 guests ∙ 3 bedrooms

Children-Friendly Cottage with Yard & Terrace | Lake View

The Berkshires, Sandisfield, Massachusetts, United States
$321
per night
Excellent(42 ratings)
$321
per night
View deal
House The Berkshires
Jun 21 - Jun 28
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Grill, Garden & Terrace

The Berkshires, Sandisfield, Massachusetts, United States
$418
per night
$418
per night
View deal
House The Berkshires
-72%
Mar 8 - Mar 15
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home with Barbeque, Garden & Terrace | Lake View

The Berkshires, Sandisfield, Massachusetts, United States
$790$267
per night
Outstanding(98 ratings)
$790$267
per night
View deal
House The Berkshires
Feb 15 - Feb 22
House ∙ 12 guests ∙ 5 bedrooms

Child-Friendly Vacation Home with Yard, Terrace & BBQ | City View | Pets Allowed

The Berkshires, Sandisfield, Massachusetts, United States
$549
per night
Outstanding(27 ratings)
$549
per night
View deal
House The Berkshires
Jun 21 - Jun 28
Free cancellation
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Hot Tub & Garden

The Berkshires, Sandisfield, Massachusetts, United States
$319
per night
$319
per night
View deal
Cabin The Berkshires
-51%
Mar 8 - Mar 15
Cabin ∙ 10 guests ∙ 7 bedrooms

Fully Equipped Charming Cabin with Terrace, Grill & Yard | Dogs Allowed

The Berkshires, Sandisfield, Massachusetts, United States
$512$287
per night
Outstanding(98 ratings)
$512$287
per night
View deal
Cottage The Berkshires
May 3 - May 10
Cottage ∙ 6 guests ∙ 4 bedrooms

Cottage with Terrace & Barbecue | Nature View

The Berkshires, Sandisfield, Massachusetts, United States
$342
per night
Outstanding(44 ratings)
$342
per night
View deal
House The Berkshires
Apr 9 - Apr 16
House ∙ 6 guests ∙ 3 bedrooms

Family-Friendly Pleasant Vacation Home with Patio, Yard & Barbecue | Dogs Allowed

The Berkshires, Sandisfield, Massachusetts, United States
$546
per night
Outstanding(2 ratings)
$546
per night
View deal
House The Berkshires
Jun 21 - Jun 28
House ∙ 14 guests ∙ 5 bedrooms

Family-Oriented Big House with Barbeque, Patio & Garden | Perfect for Remote Work

The Berkshires, Sandisfield, Massachusetts, United States
$1,056
per night
Outstanding(6 ratings)
$1,056
per night
View deal

Apartments With Balconies or Patios

House  The Berkshires
Jan 25 - Feb 1
$507
per night
House ∙ 6 guests ∙ 2 bedrooms

House with BBQ & Jacuzzi | Lake View

5.0
Outstanding(1 rating)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
Camping  The Berkshires
Mar 8 - Mar 15
$424
per night
Camping ∙ 4 guests ∙ 1 bedroom

Camping with Yard & BBQ | Good for Workation

4.9
Outstanding(9 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House  The Berkshires
Jul 19 - Jul 26
$523
per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home with Yard, Patio & Grill | Lake View | Suitable for Remote Work

4.8
Outstanding(58 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
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Best Vacation Home Deals in The Berkshires

Save up to 39%

House The Berkshires
Feb 22 - Mar 1
-39%
$391
$237
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Nice Vacation Home with Barbeque, Terrace & Yard

4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

Compare and find a rental that meets your expectations among the 33 fantastic vacation rentals from numerous vacation rental websites in The Berkshires. HomeToGo instantaneously compares all of these accommodations to help you save up to 39%!

Budget-friendly Vacation Rentals in The Berkshires

Find Fantastic yet Inexpensive Offers

House The Berkshires
Jul 12 - Jul 19
$383
per night
House ∙ 10 guests ∙ 4 bedrooms

House with 4 Rooms for 10 Persons

The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
View deal
House The Berkshires
Jul 12 - Jul 19
$363
per night
House ∙ 10 guests ∙ 4 bedrooms

House with Grill

The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
View deal
Chalet The Berkshires
Jun 21 - Jun 28
$345
per night
Chalet ∙ 8 guests ∙ 3 bedrooms

Chalet with Garden, Patio & Grill | Lake View | Perfect for Remote Work

4.9
Outstanding(33 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

Cottage The Berkshires
Jun 21 - Jun 28
$244
per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Fully Equipped Cottage with Barbecue, Terrace & Yard | Nature View | Suitable for Remote Work | Pets Allowed

4.8
Outstanding(81 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
Jul 19 - Jul 26
$191
per night
House ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Wonderful House with Terrace, Garden & Grill | Nature View

5.0
Outstanding(27 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
Apr 12 - Apr 19
$532
per night
House ∙ 6 guests ∙ 4 bedrooms

Child-Friendly Big Vacation Home with Patio & Barbecue | Lake View

5.0
Outstanding(15 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

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Popular Rental Amenities in The Berkshires

  • Pet-friendly (12)
  • Pool (2)
  • WiFi (33)
  • Air conditioning (27)
  • TV (29)
  • Fireplace (28)
  • Hot tub (4)
  • Kitchen (33)
  • Balcony/patio (11)
  • Grill (24)
  • Fishing (9)
  • Washing machine (23)

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, $495. 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).

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 33 rentals
💳 Possible discounts up to 39%
🌙 Nightly prices starting at $114
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 12 homes
🏊 Vacation rentals with pools 2 homes
491,504 reviews
The Berkshires vacation rentals have an average rating of 4.4/5 on 491,504 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 $114. Average prices for house rentals are $657 per night. Cottages in The Berkshires cost $578 per night on average.

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

There are 33 rentals from 18 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 2 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 12 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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