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

Vacation rentals in Berkshire County

Browse 2,313 available vacation homes and compared across 12 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 2,313 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Monterey
House ∙ 8 guests ∙ 5 bedrooms

Vacation home with barbeque, garden & terrace | Lake view | Good for workation

Monterey, Berkshire County, Massachusetts, United States
This waterfront house rental in Monterey features a fireplace, family-friendly yard, and parking for an unforgettable getaway.
from $463
per night
Outstanding(64 ratings)
from $463
per night
View deal
House Peru
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented house with patio, garden & BBQ | Nature view | Dogs allowed

Peru, Berkshire County, Massachusetts, United States
This house rental in Peru offers a yard, fireplace, and mountain views, perfect for families and pets, accommodating up to 6 guests.
from $197
per night
Outstanding(225 ratings)
from $197
per night
View deal
House Egremont
House ∙ 6 guests ∙ 4 bedrooms

House with patio, yard & jacuzzi | Mountain view

Egremont, Berkshire County, Massachusetts, United States
This house rental in Egremont features a kitchen, hot tub, and mountain views, perfect for families and pets alike.
from $198
per night
Excellent(36 ratings)
from $198
per night
View deal
House Monterey
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with barbecue, private pool & yard

Monterey, Berkshire County, Massachusetts, United States
This Monterey house rental for 16 features a private pool, hot tub, and a spacious yard, perfect for family gatherings.
from $1,096
per night
Outstanding(42 ratings)
from $1,096
per night
View deal
House Williamstown
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly nice vacation home with patio, private pool & barbecue | Mountain view

Williamstown, Berkshire County, Massachusetts, United States
This house rental in Williamstown features a private pool, fireplace, and mountain views, perfect for families seeking adventure.
from $615
per night
Outstanding(39 ratings)
from $615
per night
View deal
Cabin Hinsdale
Cabin ∙ 4 guests ∙ 2 bedrooms

Children-friendly spacious cabin with garden, grill & patio | Lake view

Hinsdale, Berkshire County, Massachusetts, United States
This cabin in Hinsdale features a fireplace, kitchen, and waterfront access, perfect for a family getaway with parking.
from $205
per night
Outstanding(69 ratings)
from $205
per night
View deal
House Great Barrington
House ∙ 12 guests ∙ 5 bedrooms

Family-friendly vacation home with patio, grill & yard | Nature view | Suitable for remote work

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington features a private pool, yard, and fireplace, perfect for families seeking relaxation.
from $459
per night
Outstanding(158 ratings)
from $459
per night
View deal
House Otis
House ∙ 16 guests ∙ 4 bedrooms

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

Otis, Berkshire County, Massachusetts, United States
This spacious house rental in Otis features a waterfront view, balcony, and family-friendly yard, perfect for large groups.
from $502
per night
Outstanding(137 ratings)
from $502
per night
View deal
House Lenox
House ∙ 12 guests ∙ 6 bedrooms

Vacation home with private pool & 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 $949
per night
Excellent(57 ratings)
from $949
per night
View deal
House Lee
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with patio, BBQ & hot tub | Nature view

Lee, Berkshire County, Massachusetts, United States
This waterfront house rental in Lee offers a hot tub, fireplace, and yard, perfect for family gatherings and pet-friendly fun.
from $544
per night
Outstanding(94 ratings)
from $544
per night
View deal
House Pittsfield
House ∙ 28 guests ∙ 8 bedrooms

Vacation home with hot tub, patio & garden | Nature view | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
This waterfront house rental in Pittsfield features a hot tub, mountain views, and ample space for 28 guests, perfect for families.
from $329
per night
Outstanding(175 ratings)
from $329
per night
View deal
House Monterey
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with patio, yard & barbeque | Lake view | Suitable for remote work

Monterey, Berkshire County, Massachusetts, United States
This waterfront house in Monterey features a kitchen, fireplace, hot tub, and a yard, perfect for family gatherings of 8.
from $353
per night
Outstanding(4 ratings)
from $353
per night
View deal
House Lanesborough
House ∙ 7 guests ∙ 4 bedrooms

House with hot tub, barbecue & terrace

Lanesborough, Berkshire County, Massachusetts, United States
This house rental in Lanesborough features a hot tub, fireplace, and family-friendly amenities, accommodating up to seven guests.
from $289
per night
Outstanding(21 ratings)
from $289
per night
View deal
House Hinsdale
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented house with grill, patio & yard | Suitable for remote work

Hinsdale, Berkshire County, Massachusetts, United States
This house rental in Hinsdale features a kitchen, yard, and balcony, perfect for families seeking a memorable getaway.
$411 from $387
per night
Outstanding(43 ratings)
$411 from $387
per night
View deal
House Sandisfield
House ∙ 9 guests ∙ 4 bedrooms

House with yard, patio & BBQ | Lake view

Sandisfield, Berkshire County, Massachusetts, United States
This house rental in Sandisfield offers waterfront views, a yard, and space for families or groups up to 9, plus pet-friendly amenities.
from $270
per night
Outstanding(178 ratings)
from $270
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin New Marlborough
from $226
per night
Cabin ∙ 2 guests ∙ 1 bedroom

Children-friendly cottage with patio & barbecue | Water view | Pet-friendly

4.6
Excellent(90 ratings)
New Marlborough, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House Southfield
from $231
per night
House ∙ 5 guests ∙ 2 bedrooms

House with barbeque, patio & yard | Water view

4.9
Outstanding(198 ratings)
Southfield, New Marlborough, Berkshire County
Air conditioning
View deal
House East Otis
from $197
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with BBQ

4.4
Very good(40 ratings)
East Otis, Otis, Berkshire County
Air conditioning
View deal
See all offers

Vacation homes and rentals with a yard

Cabin Hinsdale
from $411
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with grill, patio & yard | Perfect for remote work

5.0
Outstanding(43 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
Yard
View deal
Cabin New Marlborough
from $297
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Family-oriented charming cottage with patio, garden & grill | Lake view | Pets allowed

4.8
Outstanding(37 ratings)
New Marlborough, Berkshire County, Massachusetts, United States
Yard
View deal
House Williamstown
from $767
per night
House ∙ 10 guests ∙ 3 bedrooms

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

5.0
Outstanding(29 ratings)
Williamstown, Berkshire County, Massachusetts, United States
Yard
View deal
See all offers

Vacation Rentals With Fireplaces

House Windsor
from $530
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with BBQ & yard

4.8
Outstanding(15 ratings)
Windsor, Berkshire County, Massachusetts, United States
Fireplace
View deal
Cabin Sandisfield
from $293
per night
Cabin ∙ 9 guests ∙ 4 bedrooms

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

4.8
Outstanding(178 ratings)
Sandisfield, Berkshire County, Massachusetts, United States
Fireplace
View deal
House Ashley Falls
from $309
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with 5 rooms for 10 persons

4.9
Outstanding(73 ratings)
Ashley Falls, Sheffield, Berkshire County
Fireplace
View deal
See all offers

Budget-friendly rental options

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

House Otis
from $560
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with jacuzzi & BBQ | Lake view

5.0
Outstanding(24 ratings)
Otis, Berkshire County, Massachusetts, United States
View deal
House Housatonic
from $436
per night
House ∙ 14 guests ∙ 6 bedrooms

House with barbeque

5.0
Outstanding(1 rating)
Housatonic, Great Barrington, Berkshire County
View deal
House Hinsdale
from $382
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented nice house with yard, barbecue & patio | Perfect for remote work

5.0
Outstanding(43 ratings)
Hinsdale, 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

House Great Barrington
from $598
per night
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly vacation home with yard, private pool & BBQ | Perfect for remote work | Dogs allowed

4.9
Outstanding(21 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal
Cabin Otis
from $155
per night
Cabin ∙ 5 guests ∙ 2 bedrooms

Cottage with barbecue & terrace | Nature view | Pet-friendly

4.8
Outstanding(19 ratings)
Otis, Berkshire County, Massachusetts, United States
View deal
House Florida
from $309
per night
House ∙ 4 guests ∙ 2 bedrooms

House with garden

5.0
Outstanding(10 ratings)
Florida, Berkshire County, Massachusetts, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Berkshire County

How are reviews collected?
Mary H.
Guest verified by HomeToGo

Beautiful home perfect for a large family gathering. The kitchen was well stocked. We took advantage of the hot tub, piano, puzzle table, and playing games on the large dining table. Cross country skiing was available right outside the door and downhill a short drive away. Thanking you for making such a special time possible.

Reviewed on 1/22/2026 | Family
House Stockbridge
from $1,371
per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding(7 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
View deal
Christine C.
Guest verified by HomeToGo

The house was very nice, clean, and comfortable, the screened in porch was lovely, there was a great backyard with a fire-pit, and the road and neighborhood was quiet. WiFi worked great. The lake access was much closer than I thought, just a quick walk, great for kids that like to fish and swim. Roads were minimally traveled on and safe for kids to ride bikes. Nearby is a supermarket and a shopping center as well. We did not get to hike while we were there but it is clear that there is a ton of hiking nearby. All in all it was a great few days at a great house and I would highly recommend for a quiet getaway.

Reviewed on 9/24/2024 | Family
House Sherwood Forest
from $165
per night
House ∙ 7 guests ∙ 2 bedrooms
4.7
Excellent(3 ratings)
Sherwood Forest, Becket, Berkshire County
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

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 $428 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 July (7/4 – 7/11). The most affordable accommodation prices can be found in May (5/16 – 5/23).

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 March (3/27 – 4/3). June (6/13 – 6/20) has got the highest percentage of available rentals.

Information about vacation rentals in Berkshire County

🏡 Vacation rentals available 2,313 rentals
🌙 Nightly prices starting at $116
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 761 homes
🏊 Vacation rentals with pools 875 homes
7 reviews
Berkshire County vacation rentals have an average rating of 4.3/5 on 7 reviews left by travelers.

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 $116. Average prices for house rentals are $723 per night. Bed and breakfast rentals in Berkshire County cost on average $453 per night.

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

There are currently 2,313 vacation rentals from 12 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 875 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 - 33% of vacation homes are pet-friendly.

Top cities to visit

Discover Nearby Regions Worth Exploring

States near to consider for your next vacation

Most Popular Destinations

Show more
image-tag