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Holidays to The Berkshires

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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.

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 13 Oct to 14 Oct

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

4.2/5Excellent! (1,170 reviews)

"Clean, well-appointed, quiet, pleasant staff. Our only complaints were (1`) The streetlight directly outside our unit windows was not conducive to sleep. We ended up getting a dark blanket out of our car to stuff around the bedroom window so we could sleep. (2) The fireplace was non-functional--a ..."…"

Reviewed on 22 Sep 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 £82 per night from 19 Oct to 20 Oct

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! (655 reviews)

"Had a wonderful experience at the Black Swan, staff was very helpful from the sign in to check out. HATS OFF TO MISTER MEYERS FRONT DESK."…"

Reviewed on 4 Aug 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 1 Nov to 2 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! (207 reviews)

"Friendly and amazing staff.. The hotel was extremely clean"…"

Reviewed on 22 Sep 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

All-Inclusive Luxury Group Tour of Vermont
Image for All-Inclusive Luxury Group Tour of Vermont

All-Inclusive Luxury Group Tour of Vermont

£1,991
Per adult
All-Inclusive Luxury Group Tour of the Berkshires
Image for All-Inclusive Luxury Group Tour of the Berkshires

All-Inclusive Luxury Group Tour of the Berkshires

£2,788
Per adult
Zip Line Canopy Tour in the Northern Berkshires
Image for Zip Line Canopy Tour in the Northern Berkshires

Zip Line Canopy Tour in the Northern Berkshires

£65
Per adult

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

Q: What are the most popular types of hotels for a holiday to The Berkshires?
A: The Berkshires has lots of options for travellers on all budgets. If you’re seeking a bit of R&R, you’ll find no shortage of bed & breakfasts. Hotels, motels and inns are also a hit with visitors.
Q: What does a The Berkshires holiday booking with Expedia include?
A: It’s completely your choice. Bundle cars, flights and hotels, or simply select one option. You can also add some top attractions and experiences to your travel itinerary. Whatever it is you’re after, we can help you create a holiday in The Berkshires that’s right for you.
Q: What is the best way to save money on my holiday to The Berkshires?
A: Book a package with Expedia. It’s as simple as that! Flights, Hotels, Activities — put together what you need for your getaway and watch your savings grow. It’s time to plan your dream holiday (and save yourself some dollars at the same time).