Berkshires Vacation Rentals

Compare 1,607 available properties from 19 providers
Berkshires
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Best Vacation Home Deals in The Berkshires

-30%
e.g. 10/27 - 11/3
House ∙ 4 guests ∙ 2 bedrooms
Sherman, Fairfield County, Connecticut, United States
from $296 $422
VRBO
4.8
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-27%
e.g. 11/3 - 11/10
House ∙ 6 guests ∙ 3 bedrooms
Richmond, Berkshire County, Massachusetts, United States
from $135 $185
VRBO
4.4
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-23%
e.g. 10/6 - 10/13
House ∙ 6 guests ∙ 3 bedrooms
Otis, Berkshire County, Massachusetts, United States
from $229 $296
VRBO
5.0
View deal

Find the ideal accommodation for as little as $51 per night by searching and comparing the 1,557 properties listed in Berkshires. By comparing these properties, HomeToGo features the most economical offers and the highest rated accommodations in Berkshires.

Recommended Vacation Rentals in The Berkshires

Rent a vacation accommodation in The Berkshires: from $53 per night

House ∙ 6 guests ∙ 2 bedrooms
Stockbridge, Berkshire County, Massachusetts, United States
from $315
HomeAway
4.8
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Apartment ∙ 2 guests ∙ 1 bedroom
Lee, Berkshire County, Massachusetts, United States
from $65
HomeAway
4.6
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Apartment ∙ 4 guests ∙ 1 bedroom
Lee, Berkshire County, Massachusetts, United States
from $100
HomeAway
4.7
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House ∙ 4 guests ∙ 2 bedrooms
West Stockbridge, Berkshire County, Massachusetts, United States
from $185
HomeAway
5.0
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House ∙ 4 guests ∙ 2 bedrooms
New Marlborough, Berkshire County, Massachusetts, United States
from $158
HomeAway
4.6
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House ∙ 7 guests ∙ 4 bedrooms
Stockbridge, Berkshire County, Massachusetts, United States
from $247
VRBO
4.9
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House ∙ 6 guests ∙ 2 bedrooms
Hillsdale, Columbia County, New York, United States
from $161
HomeAway
5.0
View deal
House ∙ 6 guests ∙ 2 bedrooms
Lee, Berkshire County, Massachusetts, United States
from $143
HomeAway
4.9
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 2 bedrooms
Sherman, Fairfield County, Connecticut, United States
from $299
VRBO
4.8
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Fishing
House ∙ 6 guests ∙ 2 bedrooms
Sharon, Litchfield County, Connecticut, United States
from $144
VRBO
4.6
View deal
Fishing
House ∙ 6 guests ∙ 3 bedrooms
Richmond, Berkshire County, Massachusetts, United States
from $135
VRBO
4.4
View deal
Fishing
House ∙ 6 guests ∙ 2 bedrooms
Sherwood Forest, Becket, Massachusetts, United States
from $235
HomeAway
4.8
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Vacation Rentals With a Fireplace

Fireplace
House ∙ 6 guests ∙ 2 bedrooms
New Marlborough, Berkshire County, Massachusetts, United States
from $215
VRBO
5.0
View deal
Fireplace
Apartment ∙ 4 guests ∙ 1 bedroom
Pittsfield, Berkshire County, Massachusetts, United States
from $143
HomeAway
4.8
View deal
Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Otis, Berkshire County, Massachusetts, United States
from $229
VRBO
5.0
View deal
Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Stockbridge, Berkshire County, Massachusetts, United States
from $273
HomeAway
5.0
View deal
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Best Dog-Friendly Rentals

Pet-friendly
House ∙ 6 guests ∙ 5 bedrooms
Becket, Berkshire County, Massachusetts, United States
from $192
VRBO
5.0
View deal
Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
New Preston, Litchfield County, Connecticut, United States
from $295
VRBO
4.4
View deal
Pet-friendly
House ∙ 8 guests ∙ 3 bedrooms
Pawling, Dutchess County, New York, United States
from $149
VRBO
4.5
View deal
Pet-friendly
Apartment ∙ 4 guests ∙ 1 bedroom
Charlemont, Franklin County, Massachusetts, United States
from $114
VRBO
4.9
View deal
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Popular Rental Amenities in The Berkshires

  • Internet (1,290)
  • Parking (1,253)
  • No smoking (1,248)
  • TV (1,163)
  • Kitchen (1,021)
  • AC (1,012)
  • Microwave (909)
  • Yard (852)
  • Grill (808)
  • Washer (807)
  • Fishing (720)
  • Dishwasher (717)
Check above for the most selected filters in Berkshires and the number of vacation rentals that provide them. Most of the vacation rentals in 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 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 Berkshires.

Price and Availability Index 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 Berkshires are in July (7/21 - 7/28). In October (10/27 - 11/3), prices will hit an average low of $282 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 (8/4 - 8/11), as 62% of the rentals are booked. Conversely, it is in October (10/13 - 10/20) 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 the climate diagram for Berkshires. July is the warmest month in The Berkshires with average maximum temperatures of 86°. On the other hand, you could have temperatures dropping under 19° in January. The rainiest month is December while the driest month is November.

In Berkshires, more than half of the 1,557 accommodation types are house rentals, which represent 57.76% of its short-term accommodations. Additionally, they have a median size of 2,530 ft² and cost, on average, $403 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 bed & breakfast rentals, which are the other very typical property type in Berkshires. Our data shows that the standard price of bed & breakfast rentals is $279 a night for an area of 360 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.

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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 Wimdu 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