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

The Berkshires Vacation Rentals

Find 3,863 available offers from 11 partners
The Berkshires
Anytime
Guests
Ukraine Crisis Relief - Find and Offer Accommodation. Learn more

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Bed & Breakfast
Apartment
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

Show all 3,849 properties
Save up to 34%

Best Vacation Home Deals in The Berkshires

House Otis
Dec 1 - Dec 8
-34%
$320
$210 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Otis with Yard & Grill + Beautiful Views
4.9
"Excellent" (114 ratings)
Otis, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Hinsdale
Mar 25 - Apr 1
-19%
$217
$176 per night
House ∙ 6 guests ∙ 4 bedrooms
Vacation Home in Hinsdale with Yard & Grill
5.0
"Excellent" (53 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Sheffield
Mar 9 - Mar 16
-19%
$369
$300 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Grill & Yard
5.0
"Excellent" (120 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Find the ideal accommodation for as little as $79 per night by searching and comparing the 3,863 properties listed in The Berkshires. By comparing these properties, HomeToGo features the most economical offers and the highest rated accommodations in The Berkshires.

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in The Berkshires

House Peru
Mar 26 - Apr 2
$170 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Peru with Grill & Yard
5.0
"Excellent" (162 ratings)
Peru, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Chalet Hillsdale
Jun 10 - Jun 17
$166 per night
Chalet ∙ 6 guests ∙ 3 bedrooms
Beautiful Chalet in Hillsdale with Botanical Garden + Mountain Views
5.0
"Excellent" (127 ratings)
Hillsdale, Columbia County, New York, United States
Details
Vrbo
View deal
View deal
House Sandisfield
Apr 8 - Apr 15
-61%
$677
$267 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sandisfield with Yard
5.0
"Excellent" (2 ratings)
Sandisfield, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Recommended Vacation Rentals in The Berkshires

Find your perfect vacation rental in The Berkshires: from $79 per night

Cabin Charlemont
Sep 8 - Sep 15
$350 per night
Cabin ∙ 12 guests ∙ 4 bedrooms
Lovely Cabin in Charlemont with Yard & Grill
5.0
"Excellent" (137 ratings)
Charlemont, Franklin County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Hancock
Mar 25 - Apr 1
$135 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Hancock with Yard & Grill + Window Views
4.7
"Outstanding" (40 ratings)
Hancock, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Lanesborough
Dec 16 - Dec 23
$188 per night
House ∙ 6 guests ∙ 3 bedrooms
Whole Vacation Home in Lanesborough with Electric Fireplace
5.0
"Excellent" (91 ratings)
Lanesborough, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Chalet Monterey
May 15 - May 22
$185 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Chalet in Monterey with Botanical Garden
5.0
"Excellent" (109 ratings)
Monterey, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Stockbridge
May 20 - May 27
$390 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Historic Cottage in Stockbridge with Private Terrace + River View
5.0
"Excellent" (53 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Lenox
May 6 - May 13
$230 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Lenox with Yard & Grill + Panoramic Views
4.9
"Excellent" (51 ratings)
Lenox, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
House Falls Village
Jan 6 - Jan 13
$239 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Falls Village with Grill & Yard
5.0
"Excellent" (73 ratings)
Falls Village, Canaan, Connecticut, United States
Details
Vrbo
View deal
View deal
House Monterey
Feb 10 - Feb 17
$450 per night
House ∙ 12 guests ∙ 4 bedrooms
Lovely Vacation Home in Monterey with Botanical Garden
5.0
"Excellent" (102 ratings)
Monterey, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Stockbridge
May 6 - May 13
$185 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Cottage in Stockbridge with Botanical Garden + Beautiful View
5.0
"Excellent" (33 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
See all offers
Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in The Berkshires

House Canaan
Mar 9 - Mar 16
$150 per night
House ∙ 9 guests ∙ 3 bedrooms
Beautiful Vacation Home in Canaan with Grill & Yard
4.9
"Excellent" (36 ratings)
Canaan, Columbia County, New York, United States
Details
Vrbo
View deal
View deal
Cottage Hinsdale
Nov 4 - Nov 11
-28%
$163
$117 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Comfortable Cottage in Hinsdale with Grill & Yard + Lake View
4.9
"Excellent" (53 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal
Cottage Becket
Apr 8 - Apr 15
-46%
$352
$189 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
Cottage in Becket with Large Fireplace
4.2
"Very good" (31 ratings)
Becket, Berkshire County, Massachusetts, United States
Details
Vrbo
View deal
View deal

Vacation Rentals With Fireplaces

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

Cabin Fireplace Charlemont
Sep 8 - Sep 15
$351 per night
Cabin ∙ 12 guests ∙ 4 bedrooms
Lovely Cabin in Charlemont with Yard & Grill
5.0
"Excellent" (137 ratings)
Charlemont, Franklin County, Massachusetts, United States
Fireplace
Details
Vrbo
View deal
View deal
House Fireplace Canaan
Mar 9 - Mar 16
$150 per night
House ∙ 9 guests ∙ 3 bedrooms
Beautiful Vacation Home in Canaan with Grill & Yard
4.9
"Excellent" (36 ratings)
Canaan, Columbia County, New York, United States
Fireplace
Details
Vrbo
View deal
View deal
House Fireplace Otis
Mar 25 - Apr 1
-34%
$317
$208 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Otis with Yard & Grill + Beautiful Views
4.9
"Excellent" (114 ratings)
Otis, Berkshire County, Massachusetts, United States
Fireplace
Details
Vrbo
View deal
View deal
See all offers

Apartments With Balconies or Patios

Looking for a home with a balcony? Check out these vacation homes in The Berkshires with their own private patios and balconies.

House Balcony/Patio Lenox
Mar 27 - Apr 3
-32%
$239
$162 per night
House ∙ 2 guests ∙ 1 bedroom
Rental House in Lenox with Outdoor Pool + Mountain View
Lenox, Berkshire County, Massachusetts, United States
Balcony/Patio
Details
Vrbo
View deal
View deal
Cottage Balcony/Patio Stockbridge
Oct 6 - Oct 13
$186 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Cottage in Stockbridge with Botanical Garden + Beautiful View
5.0
"Excellent" (33 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Balcony/Patio
Details
Vrbo
View deal
View deal
House Balcony/Patio Sheffield
Dec 16 - Dec 23
-26%
$211
$156 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
5.0
"Excellent" (13 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
Details
Vrbo
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.

Chalet Kitchen Monterey
May 15 - May 22
$186 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Chalet in Monterey with Botanical Garden
5.0
"Excellent" (109 ratings)
Monterey, Berkshire County, Massachusetts, United States
Kitchen
Details
Vrbo
View deal
View deal
House Kitchen Falls Village
Mar 9 - Mar 16
$239 per night
House ∙ 2 guests ∙ 1 bedroom
Vacation Home in Falls Village with Grill & Yard
5.0
"Excellent" (73 ratings)
Falls Village, Canaan, Connecticut, United States
Kitchen
Details
Vrbo
View deal
View deal
Cottage Kitchen Becket
Sep 16 - Sep 23
$195 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Pleasant Cottage in Becket with Grill
5.0
"Excellent" (54 ratings)
Becket, Berkshire County, Massachusetts, United States
Kitchen
Details
Vrbo
View deal
View deal
See all offers

Popular Rental Amenities in The Berkshires

  • Internet (3,457)
  • TV (2,994)
  • Air conditioning (2,952)
  • No smoking (2,500)
  • Microwave (2,288)
  • Yard (2,097)
  • Kitchen (1,927)
  • No pets (1,904)
  • Fireplace (1,673)
  • Grill (1,471)
  • Washer (1,463)
  • Dishwasher (1,351)

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 "Internet" or "TV," which makes it a great vacation spot if you need internet access during your vacation or you never miss an episode of your favorite show. Not as many accommodations in The Berkshires are available if you want to sweat it out in a sauna or if you want a rental with a jacuzzi as "Hot tub" and "Sauna" are not often provided in The Berkshires.

The Weather in The Berkshires

max.
Min.
37°
19°
15 days 15
max.
Min.
39°
19°
15 days 15
max.
Min.
46°
28°
13 days 13
max.
Min.
61°
39°
13 days 13
max.
Min.
73°
50°
14 days 14
max.
Min.
81°
57°
13 days 13
max.
Min.
86°
64°
14 days 14
max.
Min.
84°
61°
11 days 11
max.
Min.
77°
54°
11 days 11
max.
Min.
64°
43°
12 days 12
max.
Min.
52°
32°
10 days 10
max.
Min.
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

Tue, 21 Mar
50°
32°

0%

5 h

5 mi/h

Wed, 22 Mar
53°
35°

0%

1 h

5 mi/h

Thu, 23 Mar
57°
44°

15%

0 h

12 mi/h

Fri, 24 Mar
46°
37°

10%

0 h

4 mi/h

Sat, 25 Mar
37°
33°

15%

0 h

13 mi/h

Sun, 26 Mar
42°
35°

15%

2 h

18 mi/h

Mon, 27 Mar
44°
32°

5%

3 h

12 mi/h

Accommodations for your vacation in The Berkshires

In The Berkshires, more than half of the 3,849 accommodation types are house rental, which represent 53.27% of its short-term accommodations. Additionally, they have a median size of 241 m² and cost, on average, $693 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 bed & breakfast, which are the other very typical property type in The Berkshires. Our data shows that the standard price of bed & breakfast is $350 a night for an area of 64 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

🏡 Vacation rentals 3,849 properties
💳 Possible discounts up to 37%
🌙 Nightly prices starting at $79
⭐ Popular amenities Internet, TV and Air conditioning
🐾 Pet friendly accommodations 847 properties
🏊 Vacation rentals with pools 1,310 properties

Frequently Asked Questions

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

The average accommodation in The Berkshires is priced at $79 per night. If you would like to stay in a house rental, the average price is $693 per night. A bed & breakfast The Berkshires will cost $350 per night on average.

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

There are 3,849 rentals available for booking for your vacation.

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

If you're looking to book a vacation rental in The Berkshires, the most common amenities are: Internet, TV and Air conditioning.

How many vacation rentals with pools are in The Berkshires?

There are 1,310 vacation homes from 11 providers in The Berkshires.

Are dogs allowed in vacation homes in The Berkshires?

Finding a vacation home in The Berkshires that allows pets is possible, with 847 pet-friendly available.

What's the best time of year to travel to The Berkshires?

The warmest months in The Berkshires are July and August, with temperatures around 86 °F. January and February in The Berkshires are the coldest, with 19 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in The Berkshires TripAdvisor Vacation Rentals in The Berkshires Vrbo Vacation Rentals in The Berkshires VacationRentals.com Vacation Rentals in The Berkshires HouseTrip Vacation Rentals in The Berkshires FlipKey Vacation Rentals in The Berkshires Homestay.com Vacation Rentals in The Berkshires Only-apartments Vacation Rentals in The Berkshires Interhome Vacation Rentals in The Berkshires Novasol Vacation Rentals in The Berkshires HomeEscape Vacation Rentals in The Berkshires

Top Vacation Ideas

Explore More Vacation Ideas

image-tag