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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
Cabin
House
Camping
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+
Save up to 27%

Best Vacation Home Deals The Berkshires

Apartment Winsted
Sep. 30 - Oct. 7
-27%
$339
$249 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Apartment in Winsted with Grill & Yard
Winsted, Winchester, Connecticut, United States
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House Lenox
Nov. 18 - Nov. 25
-20%
$730
$586 per night
House ∙ 4 guests ∙ 2 bedrooms
Wonderful Vacation Home in Lenox with Yard & Grill
5.0
"Excellent" (70 ratings)
Lenox, Berkshire County, Massachusetts, United States
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Book a welcoming property for as little as $113 per night by searching among the 3,062 options featured in The Berkshires. Using HomeToGo's search feature you can instantaneously search and compare the prices of each listed property to find the best deal and save up to 27%.

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Top-Rated Offers and Accommodations The Berkshires

House Sheffield
$363 per night
House ∙ 4 guests ∙ 2 bedrooms
Whole Vacation Home in Sheffield with Botanical Garden
4.9
"Excellent" (166 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Cottage Monterey
$242 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Monterey with Grill & Yard
4.7
"Outstanding" (64 ratings)
Monterey, Berkshire County, Massachusetts, United States
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House Hillsdale
$366 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Hillsdale with Grill & Yard
5.0
"Excellent" (44 ratings)
Hillsdale, Columbia County, New York, United States
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Recommended Vacation Rentals The Berkshires

Find your perfect vacation rental The Berkshires: from $113 per night

House North Canaan
$361 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in North Canaan with Private Pool
5.0
"Excellent" (8 ratings)
North Canaan, Litchfield County, Connecticut, United States
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House Monterey
$947 per night
House ∙ 9 guests ∙ 4 bedrooms
Vacation Home in Monterey with Botanical Garden + Lake Views
5.0
"Excellent" (33 ratings)
Monterey, Berkshire County, Massachusetts, United States
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Cottage Lenox
$402 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Lenox with Yard & Grill + Panoramic Views
4.9
"Excellent" (50 ratings)
Lenox, Berkshire County, Massachusetts, United States
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House Kent
$383 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Kent with Seasonal Pool
5.0
"Excellent" (1 rating)
Kent, Litchfield County, Connecticut, United States
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House Winsted
$412 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Winsted with Yard & Grill + Spectacular Views
5.0
"Excellent" (76 ratings)
Winsted, Winchester, Connecticut, United States
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Cottage Hinsdale
$190 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
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Cabin Becket
$141 per night
Cabin ∙ 5 guests ∙ 1 bedroom
Charming Cabin in Becket with Grill
4.9
"Excellent" (136 ratings)
Becket, Berkshire County, Massachusetts, United States
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House Ashfield
$255 per night
House ∙ 6 guests ∙ 3 bedrooms
Beautiful Vacation Home in Ashfield with Yard & Grill
5.0
"Excellent" (29 ratings)
Ashfield, Franklin County, Massachusetts, United States
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House Lenox
$472 per night
House ∙ 4 guests ∙ 2 bedrooms
Wonderful Vacation Home in Lenox with Yard & Grill
5.0
"Excellent" (70 ratings)
Lenox, Berkshire County, Massachusetts, United States
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Find Fantastic yet Inexpensive Rentals

Budget-friendly Rentals The Berkshires

House Cummington
$344 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Cummington with Yard & Grill + River Views
4.7
"Outstanding" (36 ratings)
Cummington, Hampshire County, Massachusetts, United States
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House Hinsdale
$253 per night
House ∙ 6 guests ∙ 4 bedrooms
Vacation Home in Hinsdale with Yard & Grill
5.0
"Excellent" (51 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
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Chalet Monterey
$282 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Chalet in Monterey with Botanical Garden
5.0
"Excellent" (105 ratings)
Monterey, Berkshire County, Massachusetts, United States
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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 Air conditioning Norfolk
$113 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Norfolk
Norfolk, Litchfield County, Connecticut, United States
Air conditioning
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Bed & Breakfast Air conditioning Norfolk
$508 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Pleasant Bed & Breakfast in Norfolk with Yard & Patio + Garden View
4.4
"Very good" (50 ratings)
Norfolk, Litchfield County, Connecticut, United States
Air conditioning
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Bed & Breakfast Air conditioning Norfolk
$496 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed And Breakfast in Norfolk with Yard & Patio + Garden Views
4.4
"Very good" (50 ratings)
Norfolk, Litchfield County, Connecticut, United States
Air conditioning
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Vacation rentals with Wi-Fi

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

Cabin Internet Norfolk
$518 per night
Cabin ∙ 8 guests ∙ 4 bedrooms
Cabin in Norfolk with Grill
Norfolk, Litchfield County, Connecticut, United States
Internet
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Bed & Breakfast Internet Norfolk
$478 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Wonderful Bed & Breakfast in Norfolk with Yard & Patio + Garden Views
4.4
"Very good" (50 ratings)
Norfolk, Litchfield County, Connecticut, United States
Internet
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Bed & Breakfast Internet Norfolk
$511 per night
Bed & Breakfast ∙ 3 guests ∙ 1 bedroom
Bed And Breakfast in Norfolk with Yard & Patio + Garden Views
4.4
"Very good" (50 ratings)
Norfolk, Litchfield County, Connecticut, United States
Internet
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations The Berkshires with private yards.

Bed & Breakfast Yard Norfolk
$515 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed And Breakfast in Norfolk with Patio & Yard + Garden Views
4.4
"Very good" (50 ratings)
Norfolk, Litchfield County, Connecticut, United States
Yard
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Bed & Breakfast Yard Norfolk
$547 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
Bed And Breakfast in Norfolk with Yard & Patio
4.4
"Very good" (50 ratings)
Norfolk, Litchfield County, Connecticut, United States
Yard
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Popular Rental Amenities The Berkshires

  • Pool (1,121)
  • Pets allowed (664)
  • Internet (3,014)
  • Air conditioning (2,600)
  • Kitchen (1,506)
  • TV (2,632)
  • Washer (1,416)
  • Parking (137)
  • Balcony/Patio (749)
  • Dishwasher (1,076)
  • Grill (1,203)
  • Jacuzzi (221)

Finding a vacation rental with a pool shouldn't be too hard The Berkshires. One-third of the vacation rentals have one. Additionally, more House rental have pools than any other type of property. They are a great choice if you go in a group of 8, as that is the number of people they can usually accommodate. Among these rentals, 83 of them are located within 2 kilometres of water.

Price and Availability Index in The Berkshires

Vacation Rental Price Information The Berkshires

We analyzed vacation houses, cottages and apartments to display a price graph showing the average price per night The Berkshires. Prices reach a peak a week in August. The price per night in a vacation rental The Berkshires this week (8/5 - 8/12) costs on average $631. The cheapest week is in November (11/11 - 11/18). Prices fall to an average of $468 per night.

Rental Availability Information The Berkshires

Find out the percentage of available rentals The Berkshires with the graph above. It is harder to find an accommodation during a week of April (4/27 - 5/4), as 90% of the rentals are booked. More accommodations are available in a week of September (9/16 - 9/23) as the booking rate is only 28%.

The Weather 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

Above are the weather conditions for The Berkshires. On average, the warmest month is July. On the contrary, the coolest month is January. Bring your umbrella in December, the rainiest month of the year!

7-Day Weather Forecast The Berkshires

Sun., 28 May
25°
13°

0%

14 h

8 km/h

Mon., 29 May
21°
11°

0%

14 h

14 km/h

Tue., 30 May
24°

15%

14 h

7 km/h

Wed., 31 May
27°
10°

15%

13 h

6 km/h

Thu., 1 Jun.
28°
13°

10%

9 h

9 km/h

Fri., 2 Jun.
28°
20°

10%

7 h

12 km/h

Sat., 3 Jun.
22°
15°

15%

3 h

6 km/h

Information about vacation rentals The Berkshires

🏡 Vacation rentals available 3,062 properties
💳 Discounts available up to 27%
🌙 Price per night from $113
⭐ Popular amenities Pool, Pets allowed and Internet
🏊 Vacation rentals with pools 1,098 properties

Frequently Asked Questions

What is the typical price of a vacation home The Berkshires?

The starting price for House rental or Bed & Breakfast rentals The Berkshires is $113 per night.

What is the typical availability of House rental The Berkshires?

September has the highest availability of House rental The Berkshires, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities The Berkshires?

The most popular amenities for rentals The Berkshires include vacation homes with Pool, Pets allowed, or Internet.

How many House rental and Bed & Breakfast rentals can I find The Berkshires?

The Berkshires has 3,062 House rental and Bed & Breakfast rentals available to book.

What's the best month to visit The Berkshires?

When booking accommodation The Berkshires, remember that the rainiest months are usually December and January, with November often being the sunniest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals The Berkshires TripAdvisor Vacation Rentals The Berkshires Vrbo Vacation Rentals The Berkshires Novasol Vacation Rentals The Berkshires Inter Chalet Vacation Rentals The Berkshires Interhome Vacation Rentals The Berkshires HouseTrip Vacation Rentals The Berkshires Belvilla Vacation Rentals The Berkshires Homestay.com Vacation Rentals The Berkshires Ski Planet Vacation Rentals The Berkshires Only-apartments Vacation Rentals The Berkshires James Villa Holidays Vacation Rentals The Berkshires

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