Berkshire County Holidays

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Top destinations in Berkshire County

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Pittsfield

Pittsfield

Our pick of the best Berkshire County Hotel Deals

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 NZ$252 per night from 8 July to 9 July
NZ$252
8 July - 9 July
includes taxes & fees
8.8/10 Excellent! (2,421 reviews)
"Vacation Villas in the Berkshires was a tremendous property. The facility was spectacular, the rooms clean, great and comfortable and the staff was so friendly and accommodating. We had the best time and I can't wait to go back."

Reviewed on 6 July 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$249 per night from 7 July to 8 July
NZ$249
7 July - 8 July
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Vert clean, incluses breakfast so so"

Reviewed on 6 July 2026

The Yankee Inn
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 NZ$300 per night from 5 Aug to 6 Aug
NZ$300
5 Aug - 6 Aug
includes taxes & fees
9/10 Wonderful! (1,023 reviews)
"This was a great place to stay. It was clean and quiet. The staff were really helpful And friendly. Although the decor is a bit dated the room was clean and comfortable. There a big kitchen (for a hotel), dining table, sitting room, separate bedroom And a big bathroom. The property also had a large ..."

Reviewed on 6 July 2026

Berkshire Mountain Lodge
See all 1,089 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 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 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.