Berkshire County Vacations & Trips from $572

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Your Berkshire County Vacation

With a Berkshire County vacation package, you can forget about the stress of planning and simply focus on experiencing what this exciting destination has on offer. Kick off your trip to Berkshire County with a few nights in Lenox visiting popular attractions like National Shrine of the Divine Mercy and Norman Rockwell Museum. Williamstown is another city that draws crowds from far and wide. Massachusetts Museum of Contemporary Art and Mount Greylock are two of the leading places to see in this destination. If you're ready to stop daydreaming and start doing, Expedia will help turn your Berkshire County vacation into reality.

Top destinations in Berkshire County

A street lined with historic buildings, including a Morgan House restaurant.

Lee

Lee
A cityscape with autumn-colored trees, historic buildings, and a mountainous backdrop.

Adams

Adams
A street lined with brick buildings, one with a red awning and a sign reading "Shear Madness Salon".

North Adams

North Adams
A town hall with a central dome and columns, surrounded by trees and people.

Lenox

Lenox
The Purple Pub with outdoor seating and autumn foliage.

Williamstown

Williamstown
A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.

Great Barrington

Great Barrington
A historic building with classical architecture, a traffic light, and a yellow taxi.

Pittsfield

Pittsfield
A river surrounded by autumn-colored trees and a forested hill.

Stockbridge

Stockbridge
A road lined with autumn-colored trees, a green house, and a mountain in the background.

Hancock

Hancock

The Latest Berkshire County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

$572
per person
Jan 14 - Jan 17
found 5 hours ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
8.2/10 Very Good! (1,009 reviews)
The woman who checked us in was courteous and friendly but neglected to tell us that we needed to request that our room be given housekeeping while we were there. So the room was just as we left it when we returned in the afternoon. We were amazed as this was unheard of in our extensive travel experience. When we went to check out there was a different woman at the desk chatting with 2 other employees. I was ignored until I asked why our room hadn't been attended to the day before, she told me I should have signed up to have it done when I checked in. I said Noone had suggested this when I checked in. She shrugged, made no apology for this and justified went on chatting with her fellow workers. Forget about customer service, these folks have never heard of it! The breakfast was poor. We would never go back, which is a shame because it's conveniently located.

Reviewed on Oct 23, 2026

Wilder House Berkshires

Wilder House Berkshires

$624
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
9.8/10 Exceptional! (67 reviews)
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.

Reviewed on Oct 19, 2026

The Perch Hotel

The Perch Hotel

$734
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Albany (ALB)
9.6/10 Exceptional! (41 reviews)
Hotel Kinsley

Hotel Kinsley

Stockade District
$647
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
9/10 Wonderful! (405 reviews)
The breakfast could have been better.

Reviewed on Oct 22, 2026

The Wiltwyck

The Wiltwyck

$627
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
9.2/10 Wonderful! (221 reviews)
Very comfortable stay and a prime location in Kingston. Will definitely be staying here again.

Reviewed on Oct 21, 2026

Find the Best Berkshire County Vacation Packages

Berkshire County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Top Sights
Bash Bish Falls State Park, Pittsfield State Forest and Tolland State Forest

Berkshire County Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$117 nightly
$131 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (2,782 reviews)
"Very easy check in. Clean and safe."

Reviewed on Oct 23, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$110 nightly
$123 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,224 reviews)
"Wonderful place to stay for short or long time. Everything is just perfect."

Reviewed on Oct 23, 2026

Berkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
Fully refundable
$77 nightly
$86 total
Nov 15 - Nov 16
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."

Reviewed on Oct 23, 2026

Quality Inn Great Barrington
See all 1,088 properties in Berkshire County
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Berkshire County attractions

A forested hillside with a clear path and a small building at the top.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)
Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this family-friendly area.
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A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
You can get tickets for a performance at Tanglewood Music Center during your trip to Lenox. While you're in the area, stroll along the lakeside.
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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)
Take a campus tour or just explore the area of Williams College, during your travels in Williamstown. In the area, take in the fascinating museums and mountain views.
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A calm river surrounded by autumn foliage.
Photo by Adnan Kakazai

Norman Rockwell Museum

9.4/10 (347 reviews)
You can spend time studying the exhibits at Norman Rockwell Museum during your travels in Stockbridge. Wander the lakeside in this quaint area.
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A building with 'MASS MoCA' written on it, surrounded by greenery and hills.
Photo by Caminante

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)
You can spend time browsing the exhibits at Massachusetts Museum of Contemporary Art in North Adams. Take in the fascinating museums while you're in the area.
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Ski Butternut

9.0/10 (134 reviews)
Hit the slopes in Great Barrington with a visit to Ski Butternut. While you're in the area, stroll along the lakeside.
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National Shrine of the Divine Mercy

9.0/10 (83 reviews)
Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.
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Lee Premium Outlets

8.2/10 (265 reviews)
You can find the perfect gifts to bring home at Lee Premium Outlets during your trip to Lee. Amble around the area's gardens or attend a sporting event.
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