Berkshires Vacation Rentals

Compare 1,234 available properties from 23 providers
The Berkshires
Save up to 17%

Best Vacation Home Deals in The Berkshires

-17%
e.g. 1/5 - 1/12
House ∙ 10 guests ∙ 3 bedrooms
Plainfield, Hampshire County, Massachusetts, United States
from $228 $275
9flats.com
5.0
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Find the ideal accommodation for as little as $49 per night by searching and comparing the 1,234 properties listed in The Berkshires. By comparing these properties, HomeToGo features the most economical offers and the highest rated accommodations in The Berkshires.

Recommended Vacation Rentals in The Berkshires

Rent a vacation accommodation in The Berkshires: from $49 per night

House ∙ 6 guests ∙ 3 bedrooms
Richmond, Berkshire County, Massachusetts, United States
from $134
VRBO
4.4
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Apartment ∙ 2 guests ∙ 1 bedroom
Lee, Berkshire County, Massachusetts, United States
from $65
VRBO
4.7
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House ∙ 4 guests ∙ 2 bedrooms
West Stockbridge, Berkshire County, Massachusetts, United States
from $258
VRBO
5.0
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House ∙ 6 guests ∙ 3 bedrooms
Peru, Berkshire County, Massachusetts, United States
from $78
VRBO
4.9
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House ∙ 6 guests ∙ 2 bedrooms
Becket, Berkshire County, Massachusetts, United States
from $150
VRBO
4.3
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Apartment ∙ 4 guests ∙ 1 bedroom
Housatonic, Great Barrington, Massachusetts, United States
from $10
VRBO
4.9
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House ∙ 5 guests ∙ 2 bedrooms
Tolland, Hampden County, Massachusetts, United States
from $181
VRBO
5.0
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Apartment ∙ 4 guests ∙ 1 bedroom
Pittsfield, Berkshire County, Massachusetts, United States
from $144
VRBO
4.8
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House ∙ 4 guests ∙ 2 bedrooms
Savoy, Berkshire County, Massachusetts, United States
from $116
VRBO
4.9
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Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 4 guests ∙ 1 bedroom
Lanesborough, Berkshire County, Massachusetts, United States
from $48
VRBO
4.8
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Fishing
House ∙ 4 guests ∙ 2 bedrooms
Sherman, Fairfield County, Connecticut, United States
from $294
VRBO
4.8
View deal
Fishing
House ∙ 4 guests ∙ 1 bedroom
East Otis, Otis, Massachusetts, United States
from $135
VRBO
4.8
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Vacation Rentals With Fireplaces

Fireplace
Apartment ∙ 4 guests ∙ 1 bedroom
Lee, Berkshire County, Massachusetts, United States
from $87
VRBO
4.6
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $75
VRBO
4.3
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Fireplace
House ∙ 4 guests ∙ 2 bedrooms
East Otis, Otis, Massachusetts, United States
from $215
VRBO
4.6
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 5 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $157
VRBO
4.9
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Pet-friendly
House ∙ 2 guests ∙ 1 bedroom
New Marlborough, Berkshire County, Massachusetts, United States
from $110
VRBO
4.0
View deal
Pet-friendly
House ∙ 3 guests ∙ 1 bedroom
Lenox, Berkshire County, Massachusetts, United States
from $106
VRBO
4.9
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Popular Rental Amenities in The Berkshires

  • Internet (1,063)
  • No smoking (1,041)
  • Parking (1,027)
  • Kitchen (987)
  • TV (976)
  • Microwave (840)
  • AC (835)
  • Grill (785)
  • Washer (758)
  • Dishwasher (664)
  • Yard (637)
  • No pets (602)
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 "TVs," which makes it a great vacation spot if you need internet access during your vacation or you want to tune out with some TV time. Not as many accommodations in The Berkshires are available if you want a rental with a jacuzzi or if you love sweating the stress away in saunas as "saunas" and "Jacuzzis" are not often provided in The Berkshires.

Price and Availability Index in The Berkshires

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 June (6/22 - 6/29). In March (3/2 - 3/9), prices will hit an average low of $290 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 December (12/22 - 12/29), as 38% of the rentals are booked. Conversely, it is in March (3/30 - 4/6) that the highest percentage of rentals are available.

The Weather in The Berkshires

37°
19°
39°
19°
46°
28°
61°
39°
73°
50°
81°
57°
86°
64°
84°
61°
77°
54°
64°
43°
52°
32°
43°
28°
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 July while the driest month is November.

Accommodations in The Berkshires

In The Berkshires, more than half of the 1,234 accommodation types are house rentals, which represent 55.73% of its short-term accommodations. Additionally, they have a median size of 2,390 ft² and cost, on average, $478 per night. Moreover, the majority of house rentals 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 hotel rooms, which are the other very typical property type in The Berkshires. Our data shows that the standard price of hotel rooms is $187 a night for an area of 380 ft².

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 1,234 properties
Food & Drinks

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.

Family Activities

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.

Local Attractions

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.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in The Berkshires VRBO Vacation Rentals in The Berkshires HomeAway Vacation Rentals in The Berkshires TripAdvisor Vacation Rentals in The Berkshires VacationRentals.com Vacation Rentals in The Berkshires HouseTrip Vacation Rentals in The Berkshires FlipKey Vacation Rentals in The Berkshires 9flats.com Vacation Rentals in The Berkshires VaycayHero Vacation Rentals in The Berkshires PerfectPlaces.com 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 Bedycasa Vacation Rentals in The Berkshires Novasol Vacation Rentals in The Berkshires HomeEscape Vacation Rentals in The Berkshires