Vacation rentals in Berkshire County - HomeToGo base64Hash Vacation rentals in Berkshire County - HomeToGo

Vacation rentals in Berkshire County

Browse 2,274 available vacation homes and compared across 13 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Cabin
    • House
    • Farmhouse

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • WiFi
    • Fireplace
    • Hot tub
    • Kitchen
    • TV
    • Balcony/patio
    • Air conditioning
    • Parking
    • Yard
    • Washing machine
    • Sauna
    • Microwave
    • Dishwasher
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Berkshire County

Discover your ideal Berkshire County vacation rental with real-time comparisons of 2,274 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Monterey
Cabin ∙ 5 guests ∙ 2 bedrooms

Fully equipped cottage with barbecue, patio & garden | Suitable for remote work | Dogs allowed

Monterey, Berkshire County, Massachusetts, United States
This Monterey cabin features a fireplace, kitchen, and yard, perfect for 5 guests and their pets to unwind and explore.
from $209
per night
Outstanding(87 ratings)
from $209
per night
View deal
House Sandisfield
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with hot tub, yard & barbecue | Nature view

Sandisfield, Berkshire County, Massachusetts, United States
This waterfront house rental in Sandisfield offers a cozy fireplace, a kitchen, and a yard, perfect for six guests.
from $467
per night
Outstanding(30 ratings)
from $467
per night
View deal
House East Otis
House ∙ 10 guests ∙ 4 bedrooms

House with yard, grill & patio | Lake view

East Otis, Otis, Berkshire County
This waterfront house in Otis features a fireplace, kitchen, balcony, and yard, perfect for family gatherings of up to 10.
from $196
per night
Outstanding(194 ratings)
from $196
per night
View deal
House North Adams
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly house with yard, grill & patio | Mountain view | Perfect for remote work

North Adams, Berkshire County, Massachusetts, United States
This waterfront house rental in North Adams features a balcony, fireplace, and yard, perfect for family gatherings and mountain views.
from $449
per night
Outstanding(105 ratings)
from $449
per night
View deal
House Stockbridge
House ∙ 24 guests ∙ 12 bedrooms

House with barbeque, terrace & garden

Stockbridge, Berkshire County, Massachusetts, United States
This spacious house rental in Stockbridge accommodates 24 guests, featuring a kitchen, spa, yard, and pet-friendly amenities.
from $691
per night
Outstanding(70 ratings)
from $691
per night
View deal
Cabin Otis
Cabin ∙ 6 guests ∙ 2 bedrooms

Cottage with barbeque, garden & patio | Lake view

Otis, Berkshire County, Massachusetts, United States
This cabin in Otis offers lakeview access, a cozy fireplace, and a yard, perfect for families and pets alike.
from $321
per night
Very good(18 ratings)
from $321
per night
View deal
House Pittsfield
House ∙ 10 guests ∙ 3 bedrooms

Children-friendly wonderful vacation home with barbeque & patio | Lake view

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house rental in Pittsfield offers a kitchen, fireplace, and parking, perfect for family gatherings of up to 10.
from $352
per night
Outstanding(98 ratings)
from $352
per night
View deal
House Lenox
House ∙ 10 guests ∙ 3 bedrooms

House with BBQ, yard & patio | Mountain view | Good for workation

Lenox, Berkshire County, Massachusetts, United States
This house rental in Lenox features a yard, mountain views, and space for 10, making it ideal for family gatherings and pets.
from $343
per night
Outstanding(17 ratings)
from $343
per night
View deal
Cabin Sandisfield
Cabin ∙ 6 guests ∙ 2 bedrooms

Cabin with garden, barbeque & patio | Nature view

Sandisfield, Berkshire County, Massachusetts, United States
This Sandisfield cabin features a fireplace, kitchen, yard, and parking, making it a perfect retreat for up to six guests and pets.
from $142
per night
Excellent(45 ratings)
from $142
per night
View deal
House Hinsdale
House ∙ 2 guests ∙ 1 bedroom

Family-oriented house with jacuzzi, terrace & garden | Suitable for remote work

Hinsdale, Berkshire County, Massachusetts, United States
This cozy house rental in Hinsdale features a yard and parking, perfect for a memorable getaway with family or friends.
from $182
per night
Outstanding(33 ratings)
from $182
per night
View deal
House Lenox
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool, hot tub & barbeque

Lenox, Berkshire County, Massachusetts, United States
This Lenox house rental features a private pool, a full kitchen, and ample space for 12, perfect for a family getaway.
from $917
per night
Excellent(61 ratings)
from $917
per night
View deal
House Hinsdale
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with barbecue, yard & patio | Nature view

Hinsdale, Berkshire County, Massachusetts, United States
This house rental in Hinsdale features a lakeview, yard, and fireplace, perfect for a family getaway with pets welcome.
from $152
per night
Outstanding(81 ratings)
from $152
per night
View deal
House Lee
House ∙ 20 guests ∙ 6 bedrooms

Child-friendly vacation home with garden, barbeque & terrace | Nature view | Perfect for remote work

Lee, Berkshire County, Massachusetts, United States
This spacious house rental in Lee features a fireplace, kitchen, yard, and parking, perfect for family gatherings of up to 20.
from $1,152
per night
Outstanding(287 ratings)
from $1,152
per night
View deal
House Great Barrington
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly house with private pool & barbecue | Perfect for remote work | Dogs allowed

Great Barrington, Berkshire County, Massachusetts, United States
This Great Barrington house rental features a private pool, fireplace, and balcony, accommodating up to 8 guests and pets.
from $452
per night
Very good(6 ratings)
from $452
per night
View deal
Cabin New Marlborough
Cabin ∙ 4 guests ∙ 2 bedrooms

Fully equipped cottage with BBQ, patio & yard | Perfect for remote work

New Marlborough, Berkshire County, Massachusetts, United States
This cozy cabin in New Marlborough offers a fireplace, kitchen, yard, and parking, perfect for a memorable getaway.
from $295
per night
Outstanding(112 ratings)
from $295
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin Becket
from $172
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Big cabin with patio, garden & BBQ | Perfect for remote work | Pets are welcome

4.5
Excellent(22 ratings)
Becket, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House Monterey
from $448
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped pleasant vacation home with yard, barbecue & patio | Dogs allowed

5.0
Outstanding(42 ratings)
Monterey, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House Sherwood Forest
from $219
per night
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented beautiful house with barbecue, garden & terrace | Nature view | Pet-friendly

4.8
Outstanding(287 ratings)
Sherwood Forest, Becket, Berkshire County
Air conditioning
View deal
See all offers

Vacation Rentals With Fireplaces

House Lee
from $457
per night
House ∙ 14 guests ∙ 5 bedrooms

Vacation home with garden, jacuzzi & patio | Lake view

4.6
Excellent(75 ratings)
Lee, Berkshire County, Massachusetts, United States
Fireplace
View deal
Cabin Sandisfield
from $301
per night
Cabin ∙ 9 guests ∙ 4 bedrooms

Fully equipped nice cabin with yard, terrace & barbecue | Pets allowed

4.8
Outstanding(70 ratings)
Sandisfield, Berkshire County, Massachusetts, United States
Fireplace
View deal
House Great Barrington
from $915
per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with BBQ, terrace & jacuzzi | Lake view | Suitable for remote work

5.0
Outstanding(78 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
View deal
See all offers

Vacation houses with Balconies or Patios

House Williamstown
from $766
per night
House ∙ 10 guests ∙ 3 bedrooms

Family-oriented beautiful vacation home with yard, terrace & hot tub | Good for workation | Pets allowed

5.0
Outstanding(38 ratings)
Williamstown, Berkshire County, Massachusetts, United States
Balcony/Patio
View deal
Cabin Lanesborough
from $275
per night
Cabin ∙ 5 guests ∙ 3 bedrooms

Cabin with jacuzzi, grill & terrace | Lake view | Suitable for remote work

5.0
Outstanding(165 ratings)
Lanesborough, Berkshire County, Massachusetts, United States
Balcony/Patio
View deal
Chalet Monterey
from $226
per night
Chalet ∙ 6 guests ∙ 2 bedrooms

Family-oriented chalet with terrace, barbecue & yard | Nature view | Dogs allowed

5.0
Outstanding(158 ratings)
Monterey, Berkshire County, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Berkshire County offering exceptional value for money

House Hinsdale
from $230
per night
House ∙ 8 guests ∙ 2 bedrooms

Vacation home with BBQ & yard | Nature view

4.6
Excellent(97 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
View deal
House Otis
from $504
per night
House ∙ 16 guests ∙ 4 bedrooms

Family-friendly house with garden, BBQ & jacuzzi | Lake view | Pets allowed

5.0
Outstanding(139 ratings)
Otis, Berkshire County, Massachusetts, United States
View deal
House Stockbridge
from $250
per night
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque, garden & patio

4.9
Outstanding(35 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal

Top-Rated Vacation rentals in Berkshire County

Book the highest-rated Berkshire County vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Cabin Lanesborough
from $206
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with garden | Nature view | Suitable for remote work

5.0
Outstanding(140 ratings)
Lanesborough, Berkshire County, Massachusetts, United States
View deal
Apartment Williamstown
from $241
per night
Apartment ∙ 2 guests ∙ 3 bedrooms

Family-friendly holiday apartment with grill, yard & patio | Perfect for remote work

5.0
Outstanding(35 ratings)
Williamstown, Berkshire County, Massachusetts, United States
View deal
House Becket
from $210
per night
House ∙ 7 guests ∙ 2 bedrooms

Fully equipped spacious house with grill & garden | Good for workation | Pet-friendly

4.8
Outstanding(32 ratings)
Becket, Berkshire County, Massachusetts, United States
View deal

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Popular Features & Amenities in Berkshire County

  • Pet-friendly (711)
  • Pool (884)
  • WiFi (2,186)
  • Fireplace (1,224)
  • Hot tub (229)
  • Kitchen (1,150)
  • TV (1,896)
  • Balcony/patio (1,060)
  • Air conditioning (2,009)
  • Parking (98)
  • Yard (1,189)
  • Washing machine (1,014)

You can find a large selection of accommodations to compare and choose from if you are looking for a rental including a pool in Berkshire County. Additionally, more hotel room provide a pool than motel. Usually, hotel room with pools in Berkshire County accommodate 8 guests and cost $455 per night. You can also compare and find an accommodation offering a pool near the water, which is the case for nearly half of the rentals there.

Price and Availability Index in Berkshire County

Click on any bar to see price and availability information

Vacation Rental Price Information in Berkshire County

We analyzed price data and input them into this graph, which shows vacation rental prices for the upcoming twelve months in Berkshire County. Vacation rental prices are their highest during June (6/26 – 7/3). The most affordable accommodation prices can be found in September (9/12 – 9/19).

Rental availability information in Berkshire County

This graph shows the level of availability for vacation rentals over the next twelve months. The week with the lowest percentage of available accommodations is in May (5/1 – 5/8). July (7/25 – 8/1) has got the highest percentage of available rentals.

Information about vacation rentals in Berkshire County

🏡 Vacation rentals available 2,274 rentals
🌙 Nightly prices starting at $129
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 782 homes
🏊 Vacation rentals with pools 904 homes

Frequently Asked Questions

What is the average price per night for a vacation rental in Berkshire County?

The price of a night's stay in Berkshire County starts at $129. Average prices for house rentals are $748 per night. Bed and breakfast rentals in Berkshire County cost on average $480 per night.

How many vacation rentals are available for booking in Berkshire County?

There are currently 2,274 vacation rentals from 13 providers in Berkshire County.

What are the most popular amenities for vacation homes in Berkshire County?

Travelers look for Pool, Pets allowed, and Internet when booking a vacation rental in Berkshire County.

How many vacation rentals with pools are there in Berkshire County?

Discover 904 vacation rentals available to book in Berkshire County.

Are pets allowed in vacation rentals in Berkshire County?

In case if you are traveling with a pet in Berkshire County - 34% of vacation homes are pet-friendly.

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