Berkshire County Holidays

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to €150 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top destinations in Berkshire County

Top Flight + Hotel Deals in Berkshire County

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Albany Airport
Hilton Garden Inn Albany Airport
Hyatt Place Albany
Hampton Inn Albany-Wolf Road (Airport)
Hampton Inn & Suites Albany-Downtown

Top hotels in Berkshire County

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is €124 per night from 16 Jun to 17 Jun
€124
per night
16 Jun - 17 Jun
9/10 Wonderful! (260 reviews)
Modern, friendly and clean
"From my kind greeting from Bobby to my checkout in the morning, my stay could not have been better. Clean and up to date rooms, a great bar and friendly staff. Will definitely come back."

Reviewed on 13 Jun 2024

Life House Berkshires
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is €155 per night from 16 Jun to 17 Jun
€155
per night
16 Jun - 17 Jun
8.4/10 Very Good! (929 reviews)
"I really liked everything about it"

Reviewed on 10 Jun 2024

Hotel Downstreet
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is €149 per night from 16 Jun to 17 Jun
€149
per night
16 Jun - 17 Jun
9/10 Wonderful! (1,000 reviews)
"AC in the room was to noise. Other than that it was all good."

Reviewed on 10 Jun 2024

The Yankee, Trademark Collection by Wyndham
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 €1,911, 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.