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

The Berkshires Vacation Rentals

Find 22 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+

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
Mar 16 - Mar 23
-13%
$591
$512 per night
House ∙ 6 guests ∙ 3 bedrooms

Lovely House in Monterey with Wood-Burning Fireplace

4.9
Outstanding (29 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Air conditioning
View deal
View deal
Cottage  The Berkshires
Apr 27 - May 4
-7%
$342
$317 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
Air conditioning
View deal
View deal
Cottage  The Berkshires
Aug 5 - Aug 12
-17%
$617
$514 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
Air conditioning
View deal
View deal
See all offers

Apartments and vacation rentals with a kitchen

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

Cabin  The Berkshires
$401 per night
Cabin ∙ 10 guests ∙ 4 bedrooms

Family Friendly Nice Cabin in Sandisfield with Botanical Garden

4.9
Outstanding (43 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Kitchen
View deal
View deal
House  The Berkshires
$631 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
Kitchen
View deal
View deal
House  The Berkshires
$291 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
Kitchen
View deal
View deal
See all offers

Vacation rentals with a fireplace

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

House  The Berkshires
$1,050 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
Fireplace
View deal
View deal
House  The Berkshires
$212 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Monterey with Yard, Grill & Patio

5.0
Outstanding (2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
View deal
House  The Berkshires
$1,370 per night
House ∙ 16 guests ∙ 6 bedrooms

House in Monterey with Yard, Grill & Pool

The Berkshires, Sandisfield, Massachusetts, United States
Fireplace
View deal
View deal
See all offers

Best Vacation Home Deals in The Berkshires

Save up to 49%

House The Berkshires
May 4 - May 11
-49%
$726
$374 per night
House ∙ 10 guests ∙ 4 bedrooms

Family Friendly House in Sandisfield with Second-Floor Balcony

4.9
Outstanding (43 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
View deal
View deal
Cabin The Berkshires
Feb 24 - Mar 2
-42%
$522
$302 per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Wonderful Cabin in Otis with Grill

5.0
Outstanding (5 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
House The Berkshires
Mar 11 - Mar 18
-35%
$2,039
$1,329 per night
House ∙ 16 guests ∙ 6 bedrooms

Vacation Home in Monterey with Yard, Grill & Pool

The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal

Compare and find the ideal vacation rental from $142 per night by searching among the 22 options featured in The Berkshires. HomeToGo instantaneously sorts all of these vacation rentals so you can save up to 35%!

Recommended Vacation Rentals in The Berkshires

Find your perfect vacation rental in The Berkshires: from $142 per night

Cottage The Berkshires
$431 per night
Cottage ∙ 10 guests ∙ 4 bedrooms

Cottage in Sandisfield with Grill

The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
Cottage The Berkshires
$342 per night
Cottage ∙ 6 guests ∙ 3 bedrooms

Cottage in Monterey with Grill & Patio

5.0
Outstanding (4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
Mobile home The Berkshires
$173 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
View deal
View deal
Cabin The Berkshires
May 25 - Jun 1
$697 per night
Cabin ∙ 7 guests ∙ 3 bedrooms

Beautiful Cabin in Monterey

The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
House The Berkshires
$602 per night
House ∙ 7 guests ∙ 4 bedrooms

Vacation Home in Sandisfield with Pool, Grill & Yard

The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
House The Berkshires
$715 per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Monterey with Sauna, Patio & Yard

The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
House The Berkshires
$344 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Sandisfield with Grill & Yard

The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
Cabin The Berkshires
Feb 24 - Mar 2
$494 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
View deal
View deal
House The Berkshires
$703 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
View deal
View deal
See all offers

Budget-friendly Rentals in The Berkshires

Find Fantastic yet Inexpensive Rentals

House The Berkshires
$585 per night
House ∙ 12 guests ∙ 4 bedrooms

House in Monterey with Botanical Garden

4.7
Excellent (21 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal
House The Berkshires
Apr 13 - Apr 20
-49%
$2,522
$1,285 per night
House ∙ 12 guests ∙ 1 bedroom

Vacation Home in Monterey with Jacuzzi

The Berkshires, Sandisfield, Massachusetts, United States
Free cancellation
View deal
View deal
House The Berkshires
$325 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
View deal
View deal

Top-Rated Offers and Accommodations in The Berkshires

Book Vacation Rentals with the Highest User Rating

House The Berkshires
Feb 24 - Mar 2
-22%
$591
$459 per night
House ∙ 6 guests ∙ 3 bedrooms

Nice House in Monterey with Wood-Burning Fireplace

4.9
Outstanding (29 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
View deal

Popular Rental Amenities in The Berkshires

  • Pool (1)
  • Pet-friendly (8)
  • WiFi (23)
  • Air conditioning (12)
  • Kitchen (23)
  • TV (22)
  • Washing machine (19)
  • Parking (2)
  • Balcony/patio (11)
  • Dishwasher (20)
  • Grill (20)
  • 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 $636 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

Thu., 22 Feb.
-2°

5%

2 h

9 km/h

Fri., 23 Feb.

70%

0 h

7 km/h

Sat., 24 Feb.
-5°
-8°

5%

4 h

23 km/h

Sun., 25 Feb.
-2°

15%

5 h

13 km/h

Mon., 26 Feb.

15%

0 h

14 km/h

Tue., 27 Feb.

15%

0 h

8 km/h

Wed., 28 Feb.

15%

0 h

7 km/h

Information about vacation rentals in The Berkshires

💳 Possible discounts up to 35%
🌙 Nightly prices starting at $142
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 7 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?

May 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.

Top cities to visit

Show more

Top Vacation Ideas

Explore More Vacation Ideas

Show more

Other nearby destinations in The Berkshires

image-tag