Berkshire County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Berkshire County

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Pittsfield

Pittsfield

Top hotels in Berkshire County

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is 3.323.372 ₫ per night from 23 Jul to 24 Jul
3.323.372 ₫
4.000.607 ₫ total
23 Jul - 24 Jul
includes taxes & fees
8.8/10 Excellent! (2,461 reviews)
"At check-in, I was advised I would be charged $21 per day for use of "amenities" (i.e., the pool, etc.). When I stated I would not be using any amenities I was told essentially, "tough luck" as they charge it to everyone anyway. Then the young girl at the front desk proceeded to put me in a room ..."

Reviewed on 20 Jul 2026

Vacation Village in the Berkshires
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 4.223.489 ₫ per night from 19 Aug to 20 Aug
4.223.489 ₫
4.717.637 ₫ total
19 Aug - 20 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very ..."

Reviewed on 17 Jul 2026

Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is 3.106.164 ₫ per night from 13 Aug to 14 Aug
3.106.164 ₫
3.469.584 ₫ total
13 Aug - 14 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Great experience. Friendly staff. Easy walk to town."

Reviewed on 18 Jul 2026

Quality Inn Great Barrington
See all 1,091 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 holiday 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 holiday package with Expedia is a smart way to save. We have over 550 air carriers and 1null000null000 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 cosy 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 holiday?
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 holiday 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 holiday 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 holiday 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

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 make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.
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