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The Berkshires Vacation Rentals

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The Berkshires
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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
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Farmhouse
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Rating
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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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Best Vacation Home Deals in The Berkshires

Save up to 72%

Cottage New Fairfield
Jan 6 - Jan 13
-72%
$292
$83 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Pleasant Cottage in New Fairfield with Exquisite Garden + Mountain Views
4.6
Excellent (101 ratings)
New Fairfield, Fairfield County, Connecticut, United States
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House Stockbridge
Dec 9 - Dec 16
-37%
$500
$314 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Stockbridge with Botanical Garden
4.9
Outstanding (111 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House Great Barrington
Nov 11 - Nov 18
-34%
$459
$301 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Great Barrington with Wood-Burning Fireplace + Incredible Views
3.8
Good (49 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Find the ideal accommodation for as little as $77 per night by searching and comparing the 3,297 properties listed in The Berkshires. By comparing these properties, HomeToGo features the most economical offers and the highest rated accommodations in The Berkshires.

Top-Rated Rentals and Accommodations in The Berkshires

Book Vacation Rental Offers with the Highest User Rating

Cabin Becket
Jul 6 - Jul 13
$109 per night
Cabin ∙ 5 guests ∙ 1 bedroom
Charming Cabin in Becket with Grill
4.9
Outstanding (189 ratings)
Becket, Berkshire County, Massachusetts, United States
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Cottage Monterey
Apr 28 - May 5
$153 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Monterey with Grill & Yard
4.7
Excellent (65 ratings)
Monterey, Berkshire County, Massachusetts, United States
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House Stockbridge
Apr 20 - Apr 27
-57%
$692
$295 per night
House ∙ 6 guests ∙ 2 bedrooms
Beautiful House in Stockbridge with Botanical Garden
4.9
Outstanding (18 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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Recommended Vacation Rentals in The Berkshires

Find your perfect vacation rental in The Berkshires: from $80 per night

Cottage New Marlborough
Oct 21 - Oct 28
$163 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Rustic Cottage in New Marlborough with Grill + Unbeatable Views
4.5
Excellent (37 ratings)
New Marlborough, Berkshire County, Massachusetts, United States
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Cottage Hinsdale
Sep 14 - Sep 21
-32%
$406
$278 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Rental Cottage in Hinsdale with Grill + Lake Views
4.7
Excellent (25 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
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Cottage Taconic
Jan 13 - Jan 20
-44%
$249
$141 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Cottage in Taconic with Yard & Grill + Mountain Views
4.8
Outstanding (170 ratings)
Taconic, Salisbury, Connecticut, United States
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House Otis
Nov 3 - Nov 10
-51%
$344
$170 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Otis with Grill + Spectacular Views
Otis, Berkshire County, Massachusetts, United States
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House Monterey
Sep 30 - Oct 7
$395 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Monterey with Yard & Grill + Great Views
4.7
Excellent (44 ratings)
Monterey, Berkshire County, Massachusetts, United States
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House Sheffield
Dec 2 - Dec 9
-64%
$582
$211 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield + Pond Views
4.7
Excellent (13 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House South Lee
Dec 16 - Dec 23
$570 per night
House ∙ 8 guests ∙ 4 bedrooms
House in South Lee with Private Patio
4.8
Outstanding (30 ratings)
South Lee, Lee, Massachusetts, United States
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Cabin Otis
Dec 9 - Dec 16
-55%
$434
$194 per night
Cabin ∙ 7 guests ∙ 3 bedrooms
Nice Cabin in Otis
4.8
Outstanding (4 ratings)
Otis, Berkshire County, Massachusetts, United States
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Cottage Lakeville
May 4 - May 11
$402 per night
Cottage ∙ 18 guests ∙ 5 bedrooms
Nice Cottage in Lakeville with Grill & Yard
4.8
Outstanding (80 ratings)
Lakeville, Salisbury, Connecticut, United States
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Budget-friendly Vacation Rentals in The Berkshires

Find Fantastic yet Inexpensive Offers

House Stephentown
Nov 17 - Nov 24
$104 per night
House ∙ 4 guests ∙ 2 bedrooms
Vacation Home in Stephentown with Grill
Stephentown, Rensselaer County, New York, United States
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Cottage Otis
Jul 20 - Jul 27
$178 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
Cottage in Otis with Grill
4.9
Outstanding (23 ratings)
Otis, Berkshire County, Massachusetts, United States
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House Copake
Dec 9 - Dec 16
-80%
$613
$124 per night
House ∙ 9 guests ∙ 3 bedrooms
House in Copake with Grill & Yard
4.2
Very good (10 ratings)
Copake, Columbia County, New York, United States
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Vacation rentals with Wi-Fi

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

House  Norfolk
$80 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Norfolk
Norfolk, Litchfield County, Connecticut, United States
Internet
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Bed and breakfast  Norfolk
$366 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
Bed And Breakfast in Norfolk with Yard & Patio + Garden Views
4.7
Excellent (161 ratings)
Norfolk, Litchfield County, Connecticut, United States
Internet
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Bed and breakfast  Norfolk
$328 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
Pleasant Bed & Breakfast in Norfolk with Yard & Patio + Garden View
4.7
Excellent (161 ratings)
Norfolk, Litchfield County, Connecticut, 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  Hancock
Nov 11 - Nov 18
$540 per night
House ∙ 14 guests ∙ 4 bedrooms
Nice Vacation Home in Hancock with Grill & Pool + Mountain Views
5.0
Outstanding (2 ratings)
Hancock, Berkshire County, Massachusetts, United States
Air conditioning
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House  Egremont
Dec 9 - Dec 16
-42%
$797
$464 per night
House ∙ 17 guests ∙ 7 bedrooms
Beautiful Vacation Home in Egremont with -The Pool + Beautiful Views
5.0
Outstanding (5 ratings)
Egremont, Berkshire County, Massachusetts, United States
Air conditioning
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House  Brookfield
Oct 13 - Oct 20
$77 per night
House ∙ 2 guests ∙ 1 bedroom
Pleasant House in Brookfield with Grill & Yard + Lake Views
5.0
Outstanding (9 ratings)
Brookfield, Fairfield County, Connecticut, United States
Air conditioning
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Vacation Rentals With Fireplaces

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

House  Copake
Apr 5 - Apr 12
-34%
$615
$405 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Copake with Yard & Grill + Incredible Views
5.0
Outstanding (29 ratings)
Copake, Columbia County, New York, United States
Fireplace
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House  Lee
Mar 9 - Mar 16
-24%
$1,500
$1,135 per night
House ∙ 20 guests ∙ 6 bedrooms
Vacation Home in Lee with Yard & Grill
4.9
Outstanding (234 ratings)
Lee, Berkshire County, Massachusetts, United States
Fireplace
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House  New Fairfield
Dec 9 - Dec 16
$325 per night
House ∙ 8 guests ∙ 3 bedrooms
Family Friendly House in New Fairfield with Decorative Fireplace
5.0
Outstanding (25 ratings)
New Fairfield, Fairfield County, Connecticut, United States
Fireplace
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Popular Rental Amenities in The Berkshires

  • Pet-friendly (667)
  • Pool (1,149)
  • WiFi (3,220)
  • Air conditioning (2,810)
  • TV (2,782)
  • Fireplace (1,498)
  • Hot tub (213)
  • Kitchen (1,631)
  • Balcony/patio (796)
  • Grill (1,337)
  • Fishing (733)
  • Washing machine (1,457)

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're dreaming of days spent poolside. Not as many accommodations in The Berkshires are available if you want a rental with a sauna or if you want a rental providing a crib as "Crib" and "Sauna" are not often provided in The Berkshires.

Price and Availability Index in The Berkshires

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Vacation Rental Price Information in The Berkshires

The price graph will give you the nightly price average for the upcoming months of the year. The most expensive dates to travel to The Berkshires are in August (8/3 - 8/10). In February (2/3 - 2/10), prices will hit an average low of $331 per night.

Rental availability information in The Berkshires

The availability graph shows the percentage of available rentals in The Berkshires. It is harder to find an accommodation during a week of August (8/31 - 9/7), as 79% of the rentals are booked. Conversely, it is in December (12/9 - 12/16) that the highest percentage of rentals are available.

The Weather in The Berkshires

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37°
19°
15 days 15
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39°
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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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73°
50°
14 days 14
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81°
57°
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°
54°
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

Tue, 26 Sep
59°
48°

10%

3 h

9 mi/h

Wed, 27 Sep
55°
46°

5%

0 h

10 mi/h

Thu, 28 Sep
48°
46°

15%

0 h

11 mi/h

Fri, 29 Sep
62°
46°

10%

0 h

4 mi/h

Sat, 30 Sep
68°
51°

15%

5 h

3 mi/h

Sun, 1 Oct
57°
51°

10%

1 h

5 mi/h

Mon, 2 Oct
64°
50°

10%

11 h

8 mi/h

Accommodations for your vacation in The Berkshires

In The Berkshires, nearly half of the 3,263 accommodation types are house rental, which represent 47.87% of its short-term accommodations. Additionally, they have a median size of 258 m² and cost, on average, $680 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 and breakfast rental, which are the other very typical property type in The Berkshires. Our data shows that the standard price of bed and breakfast rental is $373 a night for an area of 57 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 available 3,263 homes
💳 Possible discounts up to 53%
🌙 Nightly prices starting at $80
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 644 homes
🏊 Vacation rentals with pools 1,115 homes

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 $80 per night. If you would like to stay in a house rental, the average price is $680 per night. A bed and breakfast rental The Berkshires will cost on average $373 per night.

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

There are 3,263 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 1,115 rentals across 9 providers in The Berkshires.

Are dogs allowed in vacation rentals in The Berkshires?

If you are traveling with a dog in The Berkshires - 20% 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.

Get inspired for your vacation in The Berkshires

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