Berkshire County Vacations & Trips

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Top destinations in Berkshire County

FlightsFlightsHotelsHotels

Lenox

Lenox
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Williamstown

Williamstown

Berkshire County Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is NT$5,368 per night from Jun 21 to Jun 22
NT$5,368
NT$5,996 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (1,015 reviews)
"This is a wonderful modern hotel in a very center of North Adams. A view from 7th floor is picturesque. It is very clean. The room is spacious; the beds are comfortable. The pool looks good, although we didn't try that. There are a coupe of nice art exhibitions on the first floor. The coffee is good, ..."

Reviewed on 2026/6/15

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is NT$4,518 per night from Jun 21 to Jun 22
NT$4,518
NT$5,752 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (982 reviews)
"Well decorated. Staff were helpful and pleasant. The suite was very big and well stocked with everything you would need"

Reviewed on 2026/6/16

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is NT$4,070 per night from Jun 22 to Jun 23
NT$4,070
NT$4,893 total
Jun 22 - Jun 23
includes taxes & fees
8.8/10 Excellent! (2,397 reviews)
"Nice staff and property but they don’t seem to see the Hotels.com notes so room was different and there was no upgrade."

Reviewed on 2026/6/17

Vacation Village in the Berkshires
See all 1,102 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.

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

Tanglewood Music Center in Autumn, Lenox, Massachusetts

Tanglewood Music Center

9.6/5 (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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.