The Berkshires Holidays

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Your The Berkshires Holiday

With all the details organised before you go, our The Berkshires holiday packages are the easiest way to uncover this mountainous destination. Cultural experiences, laid-back lifestyle and spectacular views are just the start of the things that lure visitors here. A well-thought-out itinerary is essential for your trip to The Berkshires. Lenox, Hancock and Williamstown are among the major cities here. When you're ready to stop daydreaming and start doing, Expedia will help turn your The Berkshires holiday into reality.

The Berkshires Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Top Sights
Mount Greylock, Bash Bish Falls State Park and Natural Bridge State Park

Our pick of the best The Berkshires Hotel Deals

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 AU$169 per night from 30 Apr to 1 May
AU$169
per night
30 Apr - 1 May
9/10 Wonderful! (230 reviews)
Loved it!
"This place is so cute! My husband, my toddler and our Yorkie had a great night stay. You can check in on a kiosk and text them for anything you need! Everyone was so friendly and being pet friendly was a big bonus! Bit of a misunderstanding on my part, no complimentary breakfast."

Reviewed on 27 Apr. 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 6 May to 7 May
AU$238
per night
6 May - 7 May
8.8/10 Excellent! (868 reviews)
"What a pleasure to have the opportunity to stay in an historic inn such as the Red Lion."

Reviewed on 13 Apr. 2024

The Red Lion Inn
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 AU$202 per night from 5 May to 6 May
AU$202
per night
5 May - 6 May
9/10 Wonderful! (1,001 reviews)
"My overall experience at the Yankee was very good, my only complaint is the shower. The water took forever to warm up and when it eventually did it was moderately warm, never got hot, and the water pressure was poor. Otherwise my stay there was all I needed it to be"

Reviewed on 25 Apr. 2024

The Yankee, Trademark Collection by Wyndham
See all 1,022 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
beach holidays

Beach Holidays

Beach Holidays
family friendly holidays

Family Friendly Holidays

Family Friendly Holidays

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 homes 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.

Discover the most popular places to visit in The Berkshires

Image for 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
Image for Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Hit the slopes in Hancock with a visit to Jiminy Peak Mountain Resort. Discover the mountain views in this quaint area.

Jiminy Peak Mountain Resort
Image for Norman Rockwell Museum

Norman Rockwell Museum

5/5(1 review)

You can spend time browsing the exhibits at Norman Rockwell Museum during your trip to Stockbridge. Wander the lakeside in this quaint area.

Norman Rockwell Museum

What to do in The Berkshires

Image for Stockbridge Showdown MA Scavenger Hunt

Stockbridge Showdown MA Scavenger Hunt

AU$41
Per adult
Stockbridge Showdown MA Scavenger Hunt
See all activities in The Berkshires

More holiday ideas

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.