Berkshire County Holidays

Photo by Coby McNaughton

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Berkshire County

Landoll's Mohican Castle, Christmas lights.
FlightsFlightsHotelsHotels

Stockbridge

Stockbridge
FlightsFlightsHotelsHotels

Lee

Lee

Top hotels in Berkshire County

Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is €74 per night from 26 Apr to 27 Apr
€74
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (907 reviews)
such pretty interior design, cozy bed, nice shower, super clean great stay overall convenient parking

Reviewed on 21 Apr 2026

Berkshires Untold
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 €91 per night from 22 Apr to 23 Apr
€91
22 Apr - 23 Apr
includes taxes & fees
8.8/10 Excellent! (2,335 reviews)
While this is a good value for the money for a one bedroom with separate kitchenette and living area, this is basically 2nd or 3rd rate for a timeshare unit. Couch is uncomfortable to sit on and bed isn't the best. Didn't provide some very basics, such as dish soap to wash dishes and pans which are ...

Reviewed on 18 Apr 2026

Vacation Village in the Berkshires
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 €97 per night from 23 Apr to 24 Apr
€97
23 Apr - 24 Apr
includes taxes & fees
9/10 Wonderful! (910 reviews)
Very nice property but they need to have more amenities (restaurants, gift shop). I would stay again.

Reviewed on 20 Apr 2026

Berkshire Mountain Lodge
See all 1,119 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.