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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 3.204.230 ₫ per night from 24 Jun to 25 Jun
3.204.230 ₫
4.167.628 ₫ total
24 Jun - 25 Jun
includes taxes & fees
9/10 Wonderful! (962 reviews)
"We love the Bershire Mountain Lodge. We've stayed here five other times but this time we do have a few very minor negatives. 1) The cabinet door under the kitchenette sink had a loose hinge. We messaged the staff and requested that they wait until after we checked out to repair the hinge. We hope ..."

Reviewed on 4 Jun 2026

Berkshire Mountain Lodge
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is 3.328.807 ₫ per night from 23 Jun to 24 Jun
3.328.807 ₫
4.007.150 ₫ total
23 Jun - 24 Jun
includes taxes & fees
8.8/10 Excellent! (2,389 reviews)
"Great place just listed again for four more nights"

Reviewed on 3 Jun 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is 2.928.230 ₫ per night from 30 Jun to 1 Jul
2.928.230 ₫
3.270.822 ₫ total
30 Jun - 1 Jul
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful and well maintained and close to shipping and food"

Reviewed on 29 May 2026

The Yankee Inn
See all 1,099 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.