Airbnbs in The Berkshires - HomeToGo base64Hash

Airbnbs in The Berkshires

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Popular amenities for Airbnbs in The Berkshires

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Top-rated airbnbs in The Berkshires

Browse our top rated airbnbs offers

Dec 9 - Dec 16

-38%

~~$499~~

$311 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

House in Stockbridge with Botanical Garden

4.9

Outstanding (117 ratings)

Stockbridge, Berkshire County, Massachusetts, United States

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Jan 6 - Jan 13

-72%

~~$290~~

$83 per night

Airbnb ∙ 4 guests ∙ 1 bedroom

Pleasant Cottage in New Fairfield with Exquisite Garden + Mountain Views

4.6

Excellent (101 ratings)

New Fairfield, Fairfield County, Connecticut, United States

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Apr 28 - May 5

$153 per night

Airbnb ∙ 5 guests ∙ 2 bedrooms

Cottage in Monterey with Grill & Yard

4.7

Excellent (66 ratings)

Monterey, Berkshire County, Massachusetts, United States

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Best Deals and Discounts on Airbnbs

Save up to 58%

Nov 11 - Nov 18

-34%

~~$455~~

$298 per night

Airbnb ∙ 10 guests ∙ 4 bedrooms

House in Great Barrington with Wood-Burning Fireplace + Incredible Views

3.8

Good (50 ratings)

Great Barrington, Berkshire County, Massachusetts, United States

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Apr 20 - Apr 27

-58%

~~$693~~

$295 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

Beautiful House in Stockbridge with Botanical Garden

4.9

Outstanding (18 ratings)

Stockbridge, Berkshire County, Massachusetts, United States

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Jan 13 - Jan 20

-44%

~~$250~~

$140 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

Cottage in Taconic with Yard & Grill + Mountain Views

4.8

Outstanding (213 ratings)

Taconic, Salisbury, Connecticut, United States

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Airbnbs in The Berkshires: Top Accommodations

Oct 21 - Oct 28

$163 per night

Airbnb ∙ 2 guests ∙ 1 bedroom

Rustic Cottage in New Marlborough with Grill + Unbeatable Views

4.6

Excellent (42 ratings)

New Marlborough, Berkshire County, Massachusetts, United States

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Oct 7 - Oct 14

$395 per night

Airbnb ∙ 10 guests ∙ 5 bedrooms

House in Monterey with Yard & Grill + Great Views

4.7

Excellent (44 ratings)

Monterey, Berkshire County, Massachusetts, United States

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Apr 20 - Apr 27

-58%

~~$693~~

$295 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

Beautiful House in Stockbridge with Botanical Garden

4.9

Outstanding (18 ratings)

Stockbridge, Berkshire County, Massachusetts, United States

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Aug 24 - Aug 31

$563 per night

Airbnb ∙ 8 guests ∙ 4 bedrooms

House in South Lee with Private Patio

4.8

Outstanding (30 ratings)

South Lee, Lee, Massachusetts, United States

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Sep 14 - Sep 21

-31%

~~$403~~

$278 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

Rental Cottage in Hinsdale with Grill + Lake Views

4.7

Excellent (27 ratings)

Hinsdale, Berkshire County, Massachusetts, United States

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Nov 3 - Nov 10

-62%

~~$611~~

$233 per night

Airbnb ∙ 10 guests ∙ 4 bedrooms

Family Friendly Nice Cabin in Sandisfield with Botanical Garden

4.9

Outstanding (37 ratings)

Sandisfield, Berkshire County, Massachusetts, United States

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Jan 13 - Jan 20

-44%

~~$250~~

$140 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

Cottage in Taconic with Yard & Grill + Mountain Views

4.8

Outstanding (213 ratings)

Taconic, Salisbury, Connecticut, United States

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Nov 3 - Nov 10

-56%

~~$434~~

$192 per night

Airbnb ∙ 7 guests ∙ 3 bedrooms

Nice Cabin in Otis

4.8

Outstanding (4 ratings)

Otis, Berkshire County, Massachusetts, United States

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Nov 11 - Nov 18

-64%

~~$582~~

$211 per night

Airbnb ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Sheffield + Pond Views

4.7

Excellent (14 ratings)

Sheffield, Berkshire County, Massachusetts, United States

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Budget-friendly airbnbs in The Berkshires

Our top value vacation rentals for airbnbs

Dec 9 - Dec 16

-53%

~~$364~~

$170 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Vacation Home in Otis with Grill + Spectacular Views

5.0

Outstanding (1 rating)

Otis, Berkshire County, Massachusetts, United States

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Oct 20 - Oct 27

$199 per night

Airbnb ∙ 8 guests ∙ 2 bedrooms

Vacation Home in Hinsdale with Grill + Water Views

4.5

Excellent (67 ratings)

Hinsdale, Berkshire County, Massachusetts, United States

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Jul 20 - Jul 27

$177 per night

Airbnb ∙ 6 guests ∙ 2 bedrooms

Cottage in Otis with Grill

4.9

Outstanding (25 ratings)

Otis, Berkshire County, Massachusetts, United States

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Stay Connected: Airbnbs with Internet

$79 per night

Airbnb ∙ 5 guests ∙ 2 bedrooms

House in Norfolk

Norfolk, Litchfield County, Connecticut, United States

Internet

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$363 per night

Airbnb ∙ 3 guests ∙ 1 bedroom

Bed And Breakfast in Norfolk with Yard & Patio + Garden Views

4.7

Excellent (161 ratings)

Norfolk, Litchfield County, Connecticut, United States

Internet

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$336 per night

Airbnb ∙ 2 guests ∙ 1 bedroom

Bed And Breakfast in Norfolk with Yard & Patio + Garden Views

4.7

Excellent (161 ratings)

Norfolk, Litchfield County, Connecticut, United States

Internet

Details

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Stay Cool: Airbnbs with Air Conditioning

Dec 2 - Dec 9

-79%

~~$575~~

$124 per night

Airbnb ∙ 9 guests ∙ 3 bedrooms

House in Copake with Grill & Yard

4.2

Very good (10 ratings)

Copake, Columbia County, New York, United States

Air conditioning

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Nov 4 - Nov 11

$539 per night

Airbnb ∙ 14 guests ∙ 4 bedrooms

Nice Vacation Home in Hancock with Grill & Pool + Mountain Views

5.0

Outstanding (2 ratings)

Hancock, Berkshire County, Massachusetts, United States

Air conditioning

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Apr 20 - Apr 27

-27%

~~$473~~

$347 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Pleasant Vacation Home in West Stockbridge with Grill & Yard

4.9

Outstanding (21 ratings)

West Stockbridge, Berkshire County, Massachusetts, United States

Air conditioning

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Get Cozy: Airbnbs with Fireplace

Dec 2 - Dec 9

$325 per night

Airbnb ∙ 8 guests ∙ 3 bedrooms

Family Friendly House in New Fairfield with Decorative Fireplace

5.0

Outstanding (25 ratings)

New Fairfield, Fairfield County, Connecticut, United States

Fireplace

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Jun 8 - Jun 15

-24%

~~$1,500~~

$1,135 per night

Airbnb ∙ 20 guests ∙ 6 bedrooms

Vacation Home in Lee with Yard & Grill

4.9

Outstanding (239 ratings)

Lee, Berkshire County, Massachusetts, United States

Fireplace

Details

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Jun 15 - Jun 22

$333 per night

Airbnb ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Dalton with Yard & Grill

4.9

Outstanding (45 ratings)

Dalton, Berkshire County, Massachusetts, United States

Fireplace

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Airbnbs with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Nov 4 - Nov 11

-53%

~~$232~~

$110 per night

Airbnb ∙ 8 guests ∙ 2 bedrooms

Condo in Hancock with Jacuzzi, Grill & Yard

Hancock, Berkshire County, Massachusetts, United States

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Dec 2 - Dec 9

$75 per night

Airbnb ∙ 4 guests ∙ 2 bedrooms

Condo in South Lee with Jacuzzi, Grill & Pool

South Lee, Lee, Massachusetts, United States

Free cancellation

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Nov 11 - Nov 18

-58%

~~$4,793~~

$2,000 per night

Airbnb ∙ 24 guests ∙ 12 bedrooms

Wonderful House in Great Barrington with Private Pool + Postcard Views

Great Barrington, Berkshire County, Massachusetts, United States

Free cancellation

Details

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Airbnbs in The Berkshires for Any Type of Traveler

Traveling with a big group in The Berkshires?

HomeToGo has numerous Airbnbs in The Berkshires with 8+ bedrooms and eight or more bathrooms. Find unique Airbnbs for big groups in The Berkshires, complete with private pool, big kitchen, and lots of space to enjoy. January is the most affordable month to stay in The Berkshires with a large group, when nightly prices for Airbnbs will range from $350 to $471 per night. Start browsing our top Airbnbs for big groups and plan the perfect vacation!

Searching for a large family getaway in The Berkshires?

Take a look at HomeToGo's selection of spacious Airbnbs in The Berkshires, able to accommodate a large family with six or more beds and many washrooms. The Berkshires has lots of fun family-friendly activities to try, including hiking, swimming, biking, and many other activities. You will find lots of Airbnbs in The Berkshires come with family-friendly options, including private pools, game rooms, hot tubs, and many others. Most Airbnbs in The Berkshires will cost around $373 per day for a family of 2 people but there are lots of affordable options in The Berkshires to choose from. Start your search for family-friendly Airbnbs now!

Searching for a private getaway in The Berkshires with your spouse?

Book luxurious Airbnbs in The Berkshires for a couples getaway, complete with jacuzzi, spa, and a wonderful view of The Berkshires's stunning scenery. There are lots of romantic activities to try with your partner during your couples vacation, including hiking, swimming, biking, and many other outdoor activities. The cheapest time to book is January with prices starting at $80 per day. Search HomeToGo's best offers for romantic retreats in The Berkshires today!

Information about Airbnbs in The Berkshires

📏 Average home size	258 m²
😎 Least busy month	November
🛏️ Popular home types	House rental and Bed and breakfast rental
🌡️ Hottest months	July and August
❄️ Coldest months	January and February
🌧️ Rainiest months	16 rainy days in December and January

Frequently Asked Questions

What kinds of vacation rentals can i book for Airbnbs in The Berkshires?

We would advice checking out our selection of Bed and breakfast rental and House rental for Airbnbs in The Berkshires.

Airbnbs in The Berkshires: What is the vacation rental cost in The Berkshires?

You can get a great vacation rental for somewhere between $350 and $471 and find discounts up to 53%!

Can I find a vacation home for a large group for Airbnbs in The Berkshires?

in The Berkshires, large groups should look for House rental since they usually fit 8 guests.

Searching for something else?

Find more interesting places to stay in The Berkshires

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Airbnbs in The Berkshires

Choose the perfect vacation rental

Popular amenities for Airbnbs in The Berkshires

Find the perfect home for your stay

Pet-Friendly Airbnbs

Airbnbs with pools

Airbnbs with internet

Airbnbs with air conditioning

Top-rated airbnbs in The Berkshires

Best Deals and Discounts on Airbnbs

Airbnbs in The Berkshires: Top Accommodations

Budget-friendly airbnbs in The Berkshires

Stay Connected: Airbnbs with Internet

Stay Cool: Airbnbs with Air Conditioning

Get Cozy: Airbnbs with Fireplace

Airbnbs with Hot Tubs

Airbnbs in The Berkshires for Any Type of Traveler

Traveling with a big group in The Berkshires?

Searching for a large family getaway in The Berkshires?

Searching for a private getaway in The Berkshires with your spouse?

Information about Airbnbs in The Berkshires

Frequently Asked Questions

What kinds of vacation rentals can i book for Airbnbs in The Berkshires?

Airbnbs in The Berkshires: What is the vacation rental cost in The Berkshires?

Can I find a vacation home for a large group for Airbnbs in The Berkshires?

Searching for something else?

Find more interesting places to stay in The Berkshires

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Farmhouse

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