Berkshire County Vacations & Trips
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Top destinations in Berkshire County
Adams
Berkshire County Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
₩107,871
₩135,221 total
Nov 11 - Nov 12
includes taxes & fees
8.8/10 Excellent! (2,743 reviews)
"If you want an average time share/condo unit in a suite-like, remote mountain setting - this place is for you. If you want a hotel with room service, a restaurant and/or snack shop and/or breakfast (or other amenities) - go somewhere else. NOT what I was expecting. I don't recall seeing anywhere ..."
Reviewed on Oct 15, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
₩115,190
₩158,686 total
Nov 9 - Nov 10
includes taxes & fees
9/10 Wonderful! (1,207 reviews)
"The bath tub and the wash basin had some water clogging"
Reviewed on Oct 15, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
₩142,438
₩159,103 total
Nov 1 - Nov 2
includes taxes & 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
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.
Frequently asked questions
How much does a Berkshire County vacation package cost?
Less than you might think — from as low as , actually! By bundling hotels, flights and car rentals into a custom-made package, your Berkshire County escape is only clicks away.
How do I get a cheap travel package to Berkshire County?
Booking a Berkshire County vacation package with Expedia is a smart way to save. We have over 550 air carriers and 1,000,000 hotel options globally. With such a fabulous range to choose from, you'll have no trouble creating your dream adventure.
What are the top hotels in Berkshire County?
For properties in Great Barrington with cozy beds and friendly service, look up Hampton Inn Boston - Logan Airport and Boston Park Plaza. If you're visiting Hancock as well, you can look forward to a good night's sleep at Hilton Boston Logan Airport or Sheraton Boston, a Marriott Hotel.
How far in advance should I book my Berkshire County vacation?
While not all air carriers release ticket prices early, it's usually possible to compare international airfares on Expedia up to a year in advance. This is the time when you can score some fantastic deals. If you've left everything to the last minute, you might still be in luck. Low prices occasionally emerge a few weeks before departure.
What does an Expedia Berkshire County travel package include?
Choose from a combination of hotels, flights and rental cars. Once you've made your booking, you can add some activities and experiences. Want to pick your fare class? That's easily done too. The choice is yours when it comes to arranging your perfect Berkshire County getaway.
What should I know before booking a Berkshire County travel package?
Our prices are already low. However, you'll score even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Berkshire County Expedia vacation package?
Most definitely. Expedia has over 550 airline partners to choose from around the world. With so many choices, finding the ideal carrier to get you to Berkshire County will be easy.
If I'm not able to travel, can I cancel my Berkshire County vacation package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Berkshire County vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.
Stay near popular Berkshire County attractions
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.
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.
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.
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.
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.
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.
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
