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The Berkshires Vacation Rentals

Find 23 available offers from 10 partners
The Berkshires
Anytime
Guests
The Berkshires
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Rating
4.5+
4+

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.

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Vacation rentals with Wi-Fi

Stay connected while traveling and book a The Berkshires accommodation with high-speed internet.

Cabin  The Berkshires
May 4 - May 11
-60%
$488
$193 per night
Cabin ∙ 10 guests ∙ 4 bedrooms

Family Friendly Nice Cabin in Sandisfield with Botanical Garden

4.9
Outstanding (44 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Internet
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House  The Berkshires
Jan 4 - Jan 11
$695 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Monterey with Botanical Garden + Lake Views

5.0
Outstanding (55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Internet
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House  The Berkshires
May 4 - May 11
$495 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Sandisfield with Yard & Patio

5.0
Outstanding (26 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Internet
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to The Berkshires and book a vacation rental with air conditioning.

House  The Berkshires
Apr 13 - Apr 20
-62%
$1,482
$557 per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Monterey with Sauna, Patio & Yard

The Berkshires, Sandisfield, Massachusetts, United States
Air conditioning
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House  The Berkshires
May 4 - May 11
$249 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Sandisfield with Grill & Yard

The Berkshires, Sandisfield, Massachusetts, United States
Air conditioning
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Cottage  The Berkshires
May 4 - May 11
-55%
$324
$147 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Monterey with Grill & Patio

5.0
Outstanding (4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Air conditioning
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a The Berkshires rental with full kitchen.

Mobile home  The Berkshires
Mar 2 - Mar 9
$126 per night
Mobile home ∙ 8 guests ∙ 2 bedrooms

Nice Mobile Home in Otis with Grill

4.8
Outstanding (8 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Kitchen
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Cabin  The Berkshires
Feb 28 - Mar 6
-56%
$263
$116 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Wonderful Cabin in Otis with Grill

5.0
Outstanding (5 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Kitchen
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Cabin  The Berkshires
Feb 24 - Mar 2
-73%
$801
$220 per night
Cabin ∙ 12 guests ∙ 5 bedrooms

Cabin in Monterey with Grill, Yard & Patio

4.8
Outstanding (10 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Kitchen
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Best Vacation Home Deals in The Berkshires

Save up to 54%

House The Berkshires
Apr 13 - Apr 20
-52%
$1,519
$724 per night
House ∙ 12 guests ∙ 1 bedroom

Vacation Home in Monterey with Jacuzzi

The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
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Cabin The Berkshires
Feb 28 - Mar 6
-54%
$240
$111 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cabin in Otis with Grill

4.5
Excellent
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
May 4 - May 11
-42%
$600
$350 per night
House ∙ 12 guests ∙ 4 bedrooms

House in Monterey with Botanical Garden

4.7
Excellent (21 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Find the ideal accommodation for as little as $105 per night by searching and comparing the 23 properties listed in The Berkshires. By comparing these properties, HomeToGo features the most economical offers and the highest rated accommodations in The Berkshires.

Recommended Vacation Rentals in The Berkshires

Find your perfect vacation rental in The Berkshires: from $105 per night

House The Berkshires
May 4 - May 11
-56%
$406
$178 per night
House ∙ 10 guests ∙ 4 bedrooms

Family Friendly House in Sandisfield with Second-Floor Balcony

4.9
Outstanding (44 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
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House The Berkshires
Apr 6 - Apr 13
$179 per night
House ∙ 7 guests ∙ 3 bedrooms

House in Otis with Yard, Patio & Grill + Long-Range Views

4.9
Outstanding (35 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
May 4 - May 11
-26%
$329
$244 per night
House ∙ 6 guests ∙ 3 bedrooms

Lovely House in Monterey with Wood-Burning Fireplace

4.9
Outstanding (28 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cottage The Berkshires
May 11 - May 18
$167 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage in Monterey with Grill, Patio & Yard

4.8
Outstanding (68 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Mar 2 - Mar 9
-25%
$499
$375 per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation Home in East Otis with Grill & Patio + Window Views

4.6
Excellent (10 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
May 4 - May 11
$500 per night
House ∙ 12 guests ∙ 4 bedrooms

Lovely Vacation Home in Monterey with Grill, Patio & Yard

5.0
Outstanding (113 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Mar 16 - Mar 23
$171 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Otis with Grill & Patio + Spectacular Views

5.0
Outstanding (3 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Feb 8 - Feb 15
$428 per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home in Monterey with Perennial Garden

4.7
Excellent (56 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Aug 3 - Aug 10
$518 per night
House ∙ 16 guests ∙ 4 bedrooms

House in Otis with Granite Fireplace

4.9
Outstanding (133 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Budget-friendly Vacation Rentals in The Berkshires

Find Fantastic yet Inexpensive Offers

Cottage The Berkshires
May 4 - May 11
-60%
$608
$241 per night
Cottage ∙ 10 guests ∙ 4 bedrooms

Cottage in Sandisfield with Grill

The Berkshires, Sandisfield, Massachusetts, United States
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Chalet The Berkshires
Nov 16 - Nov 23
$190 per night
Chalet ∙ 6 guests ∙ 2 bedrooms

Chalet in Monterey with Botanical Garden

5.0
Outstanding (118 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
May 4 - May 11
$303 per night
House ∙ 6 guests ∙ 2 bedrooms

Pleasant House in Otis with Grill

5.0
Outstanding (6 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Top-Rated Rentals and Accommodations in The Berkshires

Book Vacation Rental Offers with the Highest User Rating

Cottage The Berkshires
May 4 - May 11
$324 per night
Cottage ∙ 6 guests ∙ 4 bedrooms

Bright Cottage in Tyringham with Yard, Patio & Grill

5.0
Outstanding (37 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
May 4 - May 11
$238 per night
House ∙ 8 guests ∙ 3 bedrooms

Lovely House in Otis with Grill, Patio & Yard

4.9
Outstanding (68 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cottage The Berkshires
Mar 16 - Mar 23
$128 per night
Cottage ∙ 2 guests ∙ 1 bedroom

Cottage in Monterey with Botanical Garden + Country Views

5.0
Outstanding (22 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Popular Rental Amenities in The Berkshires

  • Pet-friendly (8)
  • Pool (1)
  • WiFi (23)
  • Air conditioning (12)
  • TV (22)
  • Fireplace (21)
  • Hot tub (1)
  • Kitchen (23)
  • Balcony/patio (11)
  • Grill (21)
  • Fishing (9)
  • Washing machine (19)

Check above for the most selected filters in The Berkshires and the number of vacation rentals that provide them. Most of the vacation rentals in The Berkshires include "Pets allowed" or "Pool," which makes it a great vacation spot if you bring your pet everywhere or you want a rental with a pool. Not as many accommodations in The Berkshires are available if you don't have a dog or if you want to sweat it out in a sauna as "Sauna" and "No pets allowed" are not often provided in The Berkshires.

The Weather in The Berkshires

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37°
19°
15 days 15
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15 days 15
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28°
13 days 13
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39°
13 days 13
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14 days 14
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81°
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13 days 13
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86°
64°
14 days 14
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84°
61°
11 days 11
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77°
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11 days 11
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64°
43°
12 days 12
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52°
32°
10 days 10
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43°
28°
16 days 16
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. On average, the warmest month is July. No heat wave is expected in January, where minimum average temperatures usally hit a 19° low. The rainiest month is December while the driest month is November.

7-Day Weather Forecast in The Berkshires

Thu, 22 Feb
35°
28°

5%

2 h

5 mi/h

Fri, 23 Feb
41°
33°

70%

0 h

4 mi/h

Sat, 24 Feb
23°
17°

5%

4 h

14 mi/h

Sun, 25 Feb
33°
28°

15%

5 h

8 mi/h

Mon, 26 Feb
35°
33°

15%

0 h

9 mi/h

Tue, 27 Feb
39°
37°

15%

0 h

4 mi/h

Wed, 28 Feb
44°
44°

15%

0 h

4 mi/h

Accommodations for your vacation in The Berkshires

In The Berkshires, more than half of the 23 accommodation types are house rental, which represent 53.33% of its short-term accommodations. Additionally, they have a median size of 161 m² and cost, on average, $563 per night. Moreover, the majority of house rental in this destination can accommodate 8 people, which makes it a perfect destination for large groups. If you would like to rent something else, you can look for many other options, such as cabin, which are the other very typical property type in The Berkshires. Our data shows that the standard price of cabin is $484 a night for an area of 135 m².
Where to find the best food in The Berkshires?

Where to eat in the Berkshires

In the town of Lee, the family-friendly 51 Park Restaurant & Tavern serves American fare. The restaurant features a homey ambiance and is situated in the heart of a boutique shopping district.

If you’re looking for fine dining French cuisine, Blantyre’s Restaurant will fill the craving. Located in a castle-like hotel, guests are treated to candlelight dinners, with beautiful music filling the air.

The Castle Street Café in Barrington features a piano jazz bar with live nightly entertainment. The restaurant is casually elegant with extensive pub fare and a variety of craft beers.

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

💳 Possible discounts up to 76%
🌙 Nightly prices starting at $105
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 8 homes
1 reviews
The Berkshires vacation rentals have an average rating of 4.3/5 on 1 reviews left by travelers.

Frequently Asked Questions

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

The average accommodation in The Berkshires is priced at $105 per night. If you would like to stay in a house rental, the average price is $563 per night. A cabin The Berkshires will cost on average $484 per night.

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

There are 23 vacation homes available for booking for your upcoming vacation.

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

Most travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in The Berkshires.

How many vacation rentals with pools are there in The Berkshires?

There are 1 rentals across 10 providers in The Berkshires.

Are dogs allowed in vacation rentals in The Berkshires?

If you are traveling with a dog in The Berkshires - 35% of rentals are pet-friendly.

When is it better to travel to The Berkshires?

If looking for a vacation home in The Berkshires, consider that rainy season is typically in December or January, with November often being the driest.

Find the perfect The Berkshires home to match your style

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