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The Berkshires Vacation Rentals

Find 26 available offers from 16 partners
The Berkshires
Anytime
Guests
The Berkshires
Anytime
Guests

Popular Filters to find the Perfect Rental in The Berkshires

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Vacation rentals with Wi-Fi

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

Cottage  The Berkshires
Jun 22 - Jun 29
$371 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
Internet
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House  The Berkshires
Jun 22 - Jun 29
$908 per night
House ∙ 10 guests ∙ 4 bedrooms

Lovely Vacation Home in Monterey with Grill, Patio & Yard

5.0
Outstanding (111 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Internet
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House  The Berkshires
Jun 22 - Jun 29
$918 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
Internet
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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.

House  The Berkshires
Dec 12 - Dec 19
$1,552 per night
House ∙ 16 guests ∙ 6 bedrooms

Vacation Home in Monterey with Yard, Grill & Pool

The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
Kitchen
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House  The Berkshires
Jun 22 - Jun 29
$435 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
Kitchen
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House  The Berkshires
Jun 22 - Jun 29
-8%
$1,040
$961 per night
House ∙ 16 guests ∙ 4 bedrooms

House in Otis with Granite Fireplace

4.9
Outstanding (133 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Kitchen
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Vacation rentals with a fireplace

Get warm and cozy on cold winter nights in The Berkshires by booking a vacation home with a fireplace.

Cabin  The Berkshires
$444 per night
Cabin ∙ 10 guests ∙ 4 bedrooms

Family Friendly Nice Cabin in Sandisfield with Botanical Garden

4.9
Outstanding (89 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
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House  The Berkshires
$993 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Monterey with Botanical Garden + Lake Views

5.0
Outstanding (53 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
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Chalet  The Berkshires
$371 per night
Chalet ∙ 8 guests ∙ 3 bedrooms

Chalet in Monterey with Patio, Grill & Yard + Magic View

4.9
Outstanding (31 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
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Best Vacation Home Deals in The Berkshires

Save up to 46%

House The Berkshires
Jun 14 - Jun 21
-46%
$697
$377 per night
House ∙ 10 guests ∙ 4 bedrooms

Family Friendly House in Sandisfield with Second-Floor Balcony

4.9
Outstanding (89 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cottage The Berkshires
Jun 15 - Jun 22
-38%
$512
$315 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Monterey with Grill

The Berkshires, Sandisfield, Massachusetts, United States
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Compare and find the ideal vacation rental from $152 per night by searching among the 26 options featured in The Berkshires. HomeToGo instantaneously sorts all of these vacation rentals so you can save up to 48%!

Recommended Vacation Rentals in The Berkshires

Find your perfect vacation rental in The Berkshires: from $152 per night

House The Berkshires
$352 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful Vacation Home in Otis

The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Jun 15 - Jun 22
$649 per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Otis with Yard, Pool & Grill

The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Jul 11 - Jul 18
$630 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Sandisfield

The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
Dec 22 - Dec 29
$802 per night
House ∙ 6 guests ∙ 2 bedrooms

Pleasant House in Otis with Grill

5.0
Outstanding (9 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
$1,125 per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Monterey with Sauna, Patio & Yard

5.0
Outstanding (3 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
$763 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Sandisfield with Yard & Patio

5.0
Outstanding (27 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
$580 per night
House ∙ 12 guests ∙ 4 bedrooms

House in Monterey with Botanical Garden

4.7
Excellent (22 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Cabin The Berkshires
$343 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Wonderful Cabin in Otis with Grill

5.0
Outstanding (7 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Mobile home The Berkshires
$234 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
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Budget-friendly Rentals in The Berkshires

Find Fantastic yet Inexpensive Rentals

House The Berkshires
Sept 7 - Sept 14
$727 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Otis with Grill & Jacuzzi

The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
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Cottage The Berkshires
$349 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Monterey with Grill & Patio

5.0
Outstanding (4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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House The Berkshires
$435 per night
House ∙ 7 guests ∙ 3 bedrooms

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

4.9
Outstanding (39 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Top-Rated Offers and Accommodations in The Berkshires

Book Vacation Rentals with the Highest User Rating

Cabin The Berkshires
$618 per night
Cabin ∙ 12 guests ∙ 5 bedrooms

Cabin in Monterey with Grill, Yard & Patio

4.8
Outstanding (13 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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Popular Rental Amenities in The Berkshires

  • Pool (4)
  • Pet-friendly (8)
  • WiFi (27)
  • Air conditioning (17)
  • Kitchen (27)
  • TV (26)
  • Washing machine (25)
  • Parking (2)
  • Balcony/patio (12)
  • Dishwasher (23)
  • Grill (23)
  • Jacuzzi (1)

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 $803 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 (14).

The Weather in The Berkshires

max.
Min.

-7°
15 days 15
max.
Min.

-7°
15 days 15
max.
Min.

-2°
13 days 13
max.
Min.
16°
13 days 13
max.
Min.
23°
10°
14 days 14
max.
Min.
27°
14°
13 days 13
max.
Min.
30°
18°
14 days 14
max.
Min.
29°
16°
11 days 11
max.
Min.
25°
12°
11 days 11
max.
Min.
18°
12 days 12
max.
Min.
11°
10 days 10
max.
Min.

-2°
16 days 16
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for The Berkshires. On average, the warmest month is July. January is the coolest month, with average minimal temperature reaching -7°. According to the climate diagram, December is the rainiest month of the year in The Berkshires.

7-Day Weather Forecast in The Berkshires

Fri., 14 Jun.
26°
18°

60%

1 h

14 km/h

Sat., 15 Jun.
21°
18°

25%

5 h

15 km/h

Sun., 16 Jun.
23°
21°

10%

3 h

9 km/h

Mon., 17 Jun.
26°
23°

10%

1 h

18 km/h

Tue., 18 Jun.
31°
30°

10%

4 h

11 km/h

Wed., 19 Jun.
32°
32°

10%

6 h

12 km/h

Thu., 20 Jun.
31°
30°

15%

3 h

7 km/h

Information about vacation rentals in The Berkshires

🏡 Vacation rentals available 26 rentals
💳 Possible discounts up to 48%
🌙 Nightly prices starting at $152
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 7 homes
🏊 Vacation rentals with pools 4 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 typical availability of vacation rentals in The Berkshires?

June 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 27% 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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