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

Vacation rentals in Berkshire County

Browse 2,241 available vacation homes and compared across 11 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+

  • Booking Options

    • Instant Booking

  • 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 2,241 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

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 $260
per night
Outstanding(176 ratings)
from $260
per night
View deal
House Stockbridge
House ∙ 10 guests ∙ 4 bedrooms

House with terrace & grill

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a cozy fireplace, a full kitchen, and ample parking for an unforgettable getaway with friends.
from $194
per night
Outstanding(2 ratings)
from $194
per night
View deal
House Stockbridge
House ∙ 6 guests ∙ 3 bedrooms

House with barbeque, garden & patio

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a fireplace, kitchen, yard, and parking, perfect for a getaway with up to six guests.
from $233
per night
Outstanding(28 ratings)
from $233
per night
View deal
House Stockbridge
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped vacation home with yard, terrace & grill

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge features a kitchen, yard, balcony, and parking, accommodating up to 8 guests for a perfect getaway.
from $522
per night
Outstanding(87 ratings)
from $522
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 $467
per night
Outstanding(155 ratings)
from $467
per night
View deal
House Becket
House ∙ 14 guests ∙ 6 bedrooms

House with garden, private pool & jacuzzi | Suitable for remote work

Becket, Berkshire County, Massachusetts, United States
This Becket house rental offers a private pool, hot tub, and spacious yard, perfect for gatherings of up to 14 guests.
from $599
per night
Outstanding(29 ratings)
from $599
per night
View deal
Cabin Monterey
Cabin ∙ 5 guests ∙ 2 bedrooms

Fully equipped cottage with barbecue, patio & garden | Nature view | 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 $187
per night
Outstanding(89 ratings)
from $187
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 $490
per night
Outstanding(136 ratings)
from $490
per night
View deal
House Sandisfield
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with hot tub, pool & patio

Sandisfield, Berkshire County, Massachusetts, United States
This Sandisfield house rental features a pool, hot tub, and fireplace, perfect for a family getaway with pets welcome.
from $240
per night
from $240
per night
View deal
House Housatonic
House ∙ 14 guests ∙ 6 bedrooms

House with barbeque

Housatonic, Great Barrington, Berkshire County
This house rental in Housatonic accommodates 14 guests, offering a kitchen, parking, and a pet-friendly environment for families.
from $375
per night
Outstanding(1 rating)
from $375
per night
View deal
House Great Barrington
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented ample vacation home with grill | Water view

Great Barrington, Berkshire County, Massachusetts, United States
This waterfront house rental in Great Barrington offers a fireplace, kitchen, and sea view, perfect for family gatherings.
from $402
per night
Excellent(23 ratings)
from $402
per night
View deal
House Becket
House ∙ 5 guests ∙ 2 bedrooms

Child-friendly vacation home with BBQ & garden | Dogs allowed

Becket, Berkshire County, Massachusetts, United States
This house rental in Becket features a yard, fireplace, and kitchen, making it ideal for families and pet lovers.
from $215
per night
Outstanding(26 ratings)
from $215
per night
View deal
House Stockbridge
House ∙ 5 guests ∙ 2 bedrooms

Vacation home with grill & yard | Mountain view

Stockbridge, Berkshire County, Massachusetts, United States
This Stockbridge house rental features a kitchen, fireplace, and yard with mountain views, perfect for a family getaway with pets.
from $179
per night
from $179
per night
View deal
House Stockbridge
House ∙ 4 guests ∙ 2 bedrooms

House with terrace & grill | Beach view

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge offers beach access, a kitchen, and parking, perfect for a family getaway for four.
from $279
per night
Outstanding(67 ratings)
from $279
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 $250
per night
Outstanding(3 ratings)
from $250
per night
View deal

Vacation rentals and apartments with air conditioning

Cabin Sandisfield
from $232
per night
Cabin ∙ 9 guests ∙ 4 bedrooms

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

4.8
Outstanding(176 ratings)
Sandisfield, Berkshire County, Massachusetts, United States
Air conditioning
View deal
Cabin Stockbridge
from $381
per night
Cabin ∙ 10 guests ∙ 4 bedrooms

Cottage with barbeque & terrace

5.0
Outstanding(2 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House Monterey
from $626
per night
House ∙ 12 guests ∙ 4 bedrooms

Fully equipped nice house with yard, sauna & hot tub | Lake view | Good for workation

4.8
Outstanding(78 ratings)
Monterey, Berkshire County, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

Cabin Hinsdale
from $403
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with grill & yard | Perfect for remote work

5.0
Outstanding(17 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
Balcony
View deal
House Sherwood Forest
from $182
per night
House ∙ 7 guests ∙ 2 bedrooms

House | Water view

4.7
Excellent(3 ratings)
Sherwood Forest, Becket, Berkshire County
Balcony
View deal
Farmhouse Monterey
from $184
per night
Farmhouse ∙ 6 guests ∙ 2 bedrooms

Farm with yard & barbeque | Perfect for remote work

5.0
Outstanding(6 ratings)
Monterey, Berkshire County, Massachusetts, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House Lenox
from $334
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden & BBQ | Mountain view

4.7
Excellent(178 ratings)
Lenox, Berkshire County, Massachusetts, United States
Fireplace
View deal
House Great Barrington
from $299
per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped ample vacation home with garden | Mountain view | Pets are welcome

4.7
Excellent(45 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
View deal
House East Otis
from $202
per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with BBQ

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

Budget-friendly rental options

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

Cabin Monterey
from $276
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with barbeque | Good for workation

4.9
Outstanding(15 ratings)
Monterey, Berkshire County, Massachusetts, United States
View deal
House Otis
from $293
per night
House ∙ 8 guests ∙ 4 bedrooms

House with barbecue, patio & yard | Lake view

5.0
Outstanding(75 ratings)
Otis, Berkshire County, Massachusetts, United States
View deal
House Otis
from $276
per night
House ∙ 10 guests ∙ 4 bedrooms

House with yard, grill & patio | Nature view

5.0
Outstanding(182 ratings)
Otis, 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 Hancock
from $380
per night
House ∙ 10 guests ∙ 3 bedrooms

House with barbecue, pool & yard | Mountain view

4.9
Outstanding(87 ratings)
Hancock, Berkshire County, Massachusetts, United States
View deal
House Hinsdale
from $210
per night
House ∙ 6 guests ∙ 4 bedrooms

Vacation home with barbecue, yard & patio | Lake view

5.0
Outstanding(78 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
View deal
Cabin Hinsdale
from $223
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

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

4.9
Outstanding(69 ratings)
Hinsdale, 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?
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 $182
per night
House ∙ 7 guests ∙ 2 bedrooms
4.7
Excellent(3 ratings)
Sherwood Forest, Becket, Berkshire County
View deal

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Popular Features & Amenities in Berkshire County

  • Pet-friendly (714)
  • Pool (884)
  • WiFi (2,202)
  • Fireplace (1,236)
  • Hot tub (229)
  • Kitchen (1,157)
  • TV (1,908)
  • Balcony/patio (1,067)
  • Air conditioning (2,020)
  • Parking (98)
  • Yard (1,202)
  • Washing machine (1,030)

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 4 guests and cost $413 per night. You can also compare and find an accommodation offering a pool near the water, which is the case for more than half of the rentals there.

Information about vacation rentals in Berkshire County

🏡 Vacation rentals available 2,241 rentals
🌙 Nightly prices starting at $98
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 714 homes
🏊 Vacation rentals with pools 892 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 $98. Average prices for house rentals are $696 per night. Bed and breakfast rentals in Berkshire County cost on average $412 per night.

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

There are currently 2,241 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 892 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 - 32% of vacation homes are pet-friendly.

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