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Plan your The Berkshires holiday with Expedia

  • Our 2020 bundled deals are currently unavailable, but you can now book our 2021 holiday packages deals. Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in The Berkshires. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

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*Some hotels require you to cancel at least 24-48 hours before check-in.

2021 The Berkshires holiday deals

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Top Hotel Deals

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Hancock, MA
The price is £91 per night from 5 Nov to 6 Nov

Situated in Hancock, this condo is 0.1 mi (0.1 km) from Jiminy Peak Mountain Resort and within 6 miles (10 km) of Mount Greylock State Reservation and Pittsfield ...

4.2/5Excellent! (1,193 reviews)

"Incredible service and cleanliness. Amazing atmosphere and views and fantastic amenities."…"

Reviewed on 19 Oct 2020

Vacation Village in the Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
The price is £84 per night from 12 Nov to 13 Nov

Situated on the waterfront, this hotel is within 2 miles (3 km) of Animagic Museum of Animation, Lee Library and Greenock Country Club. The Mount and Lee Prime ...

4.2/5Excellent! (665 reviews)

"Best place to stay in The Berkshires. Is just an amazing, super clean and beautiful place to stay. Highly recommended!!!"…"

Reviewed on 13 Oct 2020

The Black Swan Lee - Lenox, Ascend Hotel Collection
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
3 out of 5
70 Pittsfield Rd, Lenox, MA
The price is £87 per night from 3 Nov to 4 Nov

Situated in Lenox, this hotel is 0.1 mi (0.2 km) from Kennedy Park and 3 mi (4.8 km) from Tanglewood Music Center. Lenox Library and Pleasant Valley Wilderness ...

4.6/5Exceptional! (224 reviews)

"Very comfortable and very clean property. Location is excellent. This is a great choice for a budget friendly, no frills, safe and comfortable stay."…"

Reviewed on 25 Oct 2020

Courtyard by Marriott Lenox 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.

Top things to do in The Berkshires

The Berkshires Holiday Packages

This mountain range in west Massachusetts combines spectacular nature, world-class cultural destinations and charming New England towns.  The Berkshires is a picturesque mountain range that runs for 98 miles (158 kilometres) along Massachusetts west border. Known for its scenic beauty and its cultural offerings, the Berkshires is one of the state’s top holiday destinations.

Bring a pair of comfortable hiking boots and explore the beautiful wilderness. Hike some of the famous Appalachian Trail, which runs through the Berkshires on its 2,160-mile (3,476.18-kilometre) journey. The Berkshires portion of the trail passes through spectacular peaks such as Mount Greylock and Mount Everett, along with small New England towns.

Explore the trees at the “living tree library” of Hebert Arboretum. This 231-acre (93.5-hectare) park lies in the city of Pittsfield, the largest town in the Berkshires. The arboretum is home to fields, forests and wildflowers. During the spring and fall, the garden is host to migrating songbirds.

Surround yourself with flowers at the Berkshire Botanical Garden in Stockbridge, 14 miles (22.5 kilometres) south of Pittsfield. Browse more than 3,000 species of plants in the botanical garden, which is one of the oldest public gardens in the United States. It was founded in 1934. Stay in Stockbridge to visit the Norman Rockwell Museum of Art, which has the world’s largest collection of work by the famous American artist. Rockwell spent the last several decades of his life in the town, and the museum displays over 500 pieces of his art. 

If you’re in Stockbridge in summer, visit Tanglewood. The music venue is the summer home of the Boston Symphony Orchestra and hosts regular music concerts.

Drive 1-hour north of Stockbridge to North Adams for the Massachusetts Museum of Contemporary Art, one of the largest and most renowned contemporary art centers in the United States. Look through 19 galleries in the converted factory space. 

The best time to visit the Berkshires is in summer, when the Boston Symphony Orchestra is in residence and many visitors flock to the mountains from New York and Boston. Cold winters are best enjoyed indoors, but there are plenty of museums, concert halls and theatres to keep visitors occupied. 

To learn more about all there is to do in the region, visit the official Berkshires of Western Massachusetts tourism website.

Frequently asked questions

How much does a The Berkshires holiday package cost?
Our The Berkshires holiday packages, which start from as low as , are an ideal way to save big. Pick your preferred hotels, flights and rental car to create your perfect trip.
If I'm not able to travel, can I cancel my The Berkshires holiday package?
You sure can, and we’re here to help. You may be able to cancel or amend your The Berkshires holiday package for free within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your travel plans suddenly change, have a look at our Customer Service Portal for more information.
How do I get a cheap travel package to The Berkshires?
Bundle your bookings with Expedia and save up to 15%. With over 400 air carriers and 321,000 hotels globally, your The Berkshires holiday package can be tailored exactly to suit your budget. With all those extra dollars, why not add in one or more interesting experiences and tours? That’s the easiest way to unlock even more bargains. The holiday you’ve always dreamed of in The Berkshires is much closer than you thought!
What are the top hotels in The Berkshires?
When it comes to hotels in Lenox, Hampton Inn & Suites Berkshires Lenox and Yankee Inn are two great options. If you’re considering heading to Williamstown, The Orchards Hotel and Hotel Williamstown MA Mohawk Trail look forward to welcoming you.
When is the best time of year to visit The Berkshires?
Anytime is a great time of year to take a break in The Berkshires, but you’ll likely score the best deals in . Prices tend to go up in , so expect to pay more for your hotel and airfares. Love sightseeing but don’t like big crowds? Lock in your The Berkshires getaway for . Typically, it’s a lot quieter than in .
How far in advance should I book my The Berkshires holiday?
It can be difficult to know exactly when is the ideal time to book your trip to The Berkshires. But usually the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels up to 12 months prior to departure. If you’re considering a last-minute getaway, no need to fret! There are unbeatable deals posted on Expedia all the time.
What does an Expedia The Berkshires travel package include?
Expedia has all you need to organise your The Berkshires trip, but how your package is structured is up to you. Choose from a combination of rental cars, hotels and flights. Looking for some tours or activities to fill in your time? Once you’ve made your booking, you can add them too. No matter your budget or style, there’s a holiday package to meet your needs.
What should I know before booking a The Berkshires travel package?
Locking in all the parts of your holiday together is an excellent way to save. Bundle your car rentals, flights and hotels into a handy package. But your options don’t end at hotels. Expedia features all types of properties, including holiday rentals like beach villas and spacious residences. You’ve got loads of choices!
Does Expedia offer Book Now, Pay Later The Berkshires holiday packages?
Pay the full cost of your package booking when you book or split it into a few installments — it’s up to you. Every jetsetter has their own financial circumstances. It’s for that reason Expedia has proudly partnered with online lender Affirm to offer a Book Now, Pay Later solution for all package bookings.
Can I choose my airline with a The Berkshires Expedia holiday package?
Yes, and with more than 550 airlines to pick from around the world, you’ve got lots of choice. Have a look through the available options and find out which airline fits your needs and budget.