Berkshire County Vacations & Trips from $1,102

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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.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

$1,102
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf.

Reviewed on Oct 14, 2026

The Perch Hotel

The Perch Hotel

Save 100% on your flight
$2,198
per person
Nov 19 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.6/10 Exceptional! (41 reviews)
**Premium Pricing Without Premium Service** This was our second stay at The Perch for Maker Camp, and unfortunately, our second disappointing experience. Last year we paid approximately $1,200 for two nights. This year, nearly $2,000 for the same room. Despite the significant price increase, the experience remained underwhelming. Both years, our promised 3 PM check-in codes never arrived, requiring us to call late in the evening just to access the property. There is no traditional front desk or evening staff on-site. The hotel markets itself as a boutique experience, yet the building shows its age, temperature cannot be adjusted without using an outdated AC unit or opening windows, and our requested air purifier wasn't even plugged in. Most disappointing was discovering that daily housekeeping wasn't included. This wasn't clearly disclosed during Expedia's booking process. We returned after a full day out untouched trash, including food we'd have removed had we known. At nearly $1,000 per night, these shortcomings are difficult to justify. Especially when the same room is advertised for approximately $300–$400 on another October weekend. I contacted Expedia seeking a partial refund, but my request was denied. As a small business owner, I don't leave negative reviews lightly. I understand demand-based pricing, but premium rates should come with premium service. I genuinely wanted to love this hotel, but after two stays, I'm left incredibly disappointed

Reviewed on Oct 13, 2026

Modern Berkshires Farmhouse w/ Porch, Fireplace & Views Beaver Creek by Avantstay

Modern Berkshires Farmhouse w/ Porch, Fireplace & Views Beaver Creek by Avantstay

Save 100% on your flight
$2,799
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
No reviews
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Save 100% on your flight
$3,494
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
No reviews
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Save 100% on your flight
$14,243
per person
Nov 19 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
No reviews

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
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$115 nightly
$128 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (1,207 reviews)
"The bath tub and the wash basin had some water clogging"

Reviewed on Oct 15, 2026

Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."

Reviewed on Oct 14, 2026

The Yankee Inn
See all 1,092 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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