The Berkshires Vacation Rentals - HomeToGo base64Hash The Berkshires Vacation Rentals - HomeToGo

The Berkshires Vacation Rentals

Find 35 available home rentals from 14 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
    • Air conditioning
    • Kitchen
    • TV
    • Washing machine
    • Parking
    • Balcony/patio
    • Dishwasher
    • Jacuzzi
    • Fireplace
    • Yard
    • Microwave
    • Sauna
    • Crib
    Show more

  • Accommodation type

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

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in The Berkshires

Find your perfect vacation rental in The Berkshires from just $170 per night!

Cabin The Berkshires
Cabin ∙ 12 guests ∙ 4 bedrooms

Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $1,493
per night
from $1,493
per night
View deal
Cabin The Berkshires
Cabin ∙ 12 guests ∙ 5 bedrooms

Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $603
per night
from $603
per night
View deal
Cabin The Berkshires
Cabin ∙ 6 guests ∙ 3 bedrooms

83 m² Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $332
per night
Outstanding(1 rating)
from $332
per night
View deal
Cabin The Berkshires
Cabin ∙ 6 guests ∙ 3 bedrooms

83 m² Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $402
per night
from $402
per night
View deal
House The Berkshires
House ∙ 10 guests ∙ 4 bedrooms

184 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $459
per night
from $459
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 5 bedrooms

214 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $622
per night
Outstanding(59 ratings)
from $622
per night
View deal
House The Berkshires
House ∙ 4 guests ∙ 2 bedrooms

79 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $201
per night
Outstanding(27 ratings)
from $201
per night
View deal
Chalet The Berkshires
Chalet ∙ 6 guests ∙ 2 bedrooms

125 m² Chalet

The Berkshires, Sandisfield, Massachusetts, United States
from $288
per night
Outstanding(136 ratings)
from $288
per night
View deal
Cabin The Berkshires
Cabin ∙ 2 guests ∙ 1 bedroom

Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $208
per night
Outstanding(55 ratings)
from $208
per night
View deal
Cabin The Berkshires
Cabin ∙ 6 guests ∙ 3 bedrooms

98 m² Cabin

The Berkshires, Sandisfield, Massachusetts, United States
from $387
per night
Excellent(48 ratings)
from $387
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 3 bedrooms

House

The Berkshires, Sandisfield, Massachusetts, United States
from $296
per night
from $296
per night
View deal
Farmhouse The Berkshires
Farmhouse ∙ 8 guests ∙ 4 bedrooms

Farmhouse

The Berkshires, Sandisfield, Massachusetts, United States
from $823
per night
from $823
per night
View deal
House The Berkshires
House ∙ 8 guests ∙ 3 bedrooms

153 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $418
per night
Outstanding(48 ratings)
from $418
per night
View deal
House The Berkshires
House ∙ 6 guests ∙ 3 bedrooms

223 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $865
per night
Outstanding(28 ratings)
from $865
per night
View deal
House The Berkshires
House ∙ 6 guests ∙ 4 bedrooms

251 m² House

The Berkshires, Sandisfield, Massachusetts, United States
from $460
per night
from $460
per night
View deal

Apartments with a balcony or patio

House The Berkshires
from $715 per night
House ∙ 6 guests ∙ 2 bedrooms

211 m² House

5.0
Outstanding(1 rating)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House The Berkshires
from $391 per night
House ∙ 6 guests ∙ 3 bedrooms

148 m² House

4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
House The Berkshires
from $366 per night
House ∙ 8 guests ∙ 3 bedrooms

232 m² House

4.9
Outstanding(74 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony/Patio
View deal
See all offers

Best vacation rentals with a balcony

House The Berkshires
from $404 per night
House ∙ 6 guests ∙ 3 bedrooms

147 m² House

4.9
Outstanding(55 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony
View deal
Cabin The Berkshires
from $506 per night
6 guests ∙ 3 bedrooms

Cabin

5.0
Outstanding(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony
View deal
House The Berkshires
from $578 per night
House ∙ 10 guests ∙ 5 bedrooms

372 m² House

4.7
Excellent(48 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Balcony
View deal
See all offers

Vacation homes and cottages with a garden

House The Berkshires
from $1,498 per night
House ∙ 16 guests ∙ 6 bedrooms

415 m² House

5.0
Outstanding(1 rating)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
House The Berkshires
from $1,025 per night
8 guests ∙ 5 bedrooms

House

5.0
Outstanding(39 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
Cabin The Berkshires
from $299 per night
Cabin ∙ 5 guests ∙ 2 bedrooms

119 m² Cabin

4.8
Outstanding(81 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
Yard
View deal
See all offers

Budget-friendly Rentals in The Berkshires

Find Fantastic yet Inexpensive Rentals

House The Berkshires
from $564 per night
House ∙ 10 guests ∙ 4 bedrooms

184 m² House

The Berkshires, Sandisfield, Massachusetts, United States
View deal
Cabin The Berkshires
from $330 per night
Cabin ∙ 6 guests ∙ 4 bedrooms

130 m² Cabin

5.0
Outstanding(44 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $768 per night
7 guests ∙ 3 bedrooms

House

4.8
Outstanding(18 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal

Top-Rated Offers and Accommodations in The Berkshires

Book Vacation Rentals with the Highest User Rating

House The Berkshires
from $1,493 per night
House ∙ 16 guests ∙ 6 bedrooms

415 m² House

4.5
Excellent(8 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $501 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(4 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
View deal
House The Berkshires
from $449 per night
House ∙ 7 guests ∙ 4 bedrooms

186 m² House

5.0
Outstanding(2 ratings)
The Berkshires, Sandisfield, Massachusetts, United States
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 Rental Amenities in The Berkshires

  • Pool (1)
  • Pet-friendly (10)
  • WiFi (36)
  • Air conditioning (28)
  • Kitchen (36)
  • TV (27)
  • Washing machine (30)
  • Parking (2)
  • Balcony/patio (13)
  • Dishwasher (23)
  • Grill (28)
  • Jacuzzi (8)

If you want to bring your pet, you can easily find a pet-friendly vacation home in The Berkshires. Also, pet-friendly vacation homes in The Berkshires have an average price of $713 per night. You can also find different vacation home options if you would like to rent near the city center, as a few of the pet-friendly accommodations are less than 2 mile away from the center of the city (0).

Information about vacation rentals in The Berkshires

🏡 Vacation rentals available 35 rentals
🌙 Nightly prices starting at $170
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 9 homes
3 reviews
The Berkshires vacation rentals have an average rating of 3.7/5 on 3 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in The Berkshires?

June has the highest availability of House rental in The Berkshires, so you can expect a lot of vacation rentals available, even for last-minute bookings.

What are the most popular vacation home amenities in The Berkshires?

The most popular amenities for rentals in The Berkshires include vacation homes with Pool, Pets allowed, or Internet.

Are there pet-friendly vacation rentals in The Berkshires?

If you're travelling with a dog, over 26% of vacation rentals in The Berkshires are pet-friendly.

What's the best month to book a vacation rental in The Berkshires?

When booking a vacation rental in The Berkshires, remember that the rainiest months are usually December and January, with November often being the sunniest.

Provinces nearby to consider for your next vacation

Top Vacation Destinations

Show more
image-tag