The Berkshires Holidays

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top hotels in The Berkshires

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 €113 per night from 27 Aug to 28 Aug
€113
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,931 reviews)
"Studio was nice and spacious. I got there late and left early so didn’t take advantage of amenities but they looked nice."

Reviewed on 5 Aug 2025

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
8.8/10 Excellent! (548 reviews)
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."

Reviewed on 9 Aug 2025

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Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is €68 per night from 24 Aug to 25 Aug
€68
24 Aug - 25 Aug
includes taxes & fees
5.2/10 (763 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on 2 Aug 2025

FairBridge Inn Express
See all 1,109 properties in The Berkshires
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.

Popular places to visit

Tanglewood Music Center

Tanglewood Music Center

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.

Tanglewood Music Center

National Shrine of the Divine Mercy

Learn about the local history of Stockbridge when you spend time at National Shrine of the Divine Mercy. While you're in the area, stroll along the lakeside.

National Shrine of the Divine Mercy

Naumkeag Museum

You can spend time studying the exhibits at Naumkeag Museum in Stockbridge. While you're in the area, stroll along the lakeside.

Naumkeag Museum

Frequently asked questions

How much does a The Berkshires holiday package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as . You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to The Berkshires?
Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires holiday package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 properties around the world. Whether you're holidaying with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.
What are the top hotels in The Berkshires?
Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travellers.
How far in advance should I book my The Berkshires holiday?
Travellers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia The Berkshires travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organising your The Berkshires trip, you're in charge!
What should I know before booking a The Berkshires travel package?
Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including holiday rentals such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.
If I'm not able to travel, can I cancel my The Berkshires holiday package?
Don't stress if you're rethinking your The Berkshires holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.