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Most frequently booked The Berkshires hotels

C$126
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 out of 5.0 435 Laurel St, Lee, MA
4.6/5
(5 Reviews)
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 Outlets are also within 3 miles (5 km).
 
C$145
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 out of 5.0 70 Pittsfield Rd, Lenox, MA
4/5
(1 Reviews)
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 Sanctuary are also within 2 miles (3 km).
 
C$130
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 out of 5.0 276 Brodie Mountain Rd, Hancock, MA
4/5
(28 Reviews)
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 State Reservation Visitor Center. Waubeeka Golf Links and New Lebanon Library are also within 12 miles (20 km).
 

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C$84
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2.0 out of 5.0 42 Stockbridge Rd, West Stockbridge, MA
2.8/5
(13 Reviews)
Situated near the beach, this motel is 2.4 mi (3.8 km) from Berkshire Botanical Garden and within 6 miles (10 km) of Tanglewood Music Center and Norman Rockwell Museum. Chesterwood and Mission House are also within 6 miles (10 km).
 
C$73
Wagon Wheel Inn

Wagon Wheel Inn

2.0 out of 5.0 484 Pittsfield Rd, PO Box 808, Lenox, MA
3.2/5
(10 Reviews)
Located in the heart of Lenox, this motel is within 3 miles (5 km) of Arrowhead Museum, Canoe Meadows Wildlife Sanctuary and Pleasant Valley Wilderness Sanctuary. Tanglewood Music Center and Bousquet Ski Area are also within 6 miles (10 km).
 
C$86
Lantern House Motel

Lantern House Motel

2.5 out of 5.0 256 Stockbridge Road, Great Barrington, MA
4.3/5
(18 Reviews)
Situated in the mountains, this motel is 1.8 mi (2.9 km) from Lake Mansfield Park and 2.5 mi (4 km) from Ski Butternut. Mahaiwe Performing Arts Center and Beartown State Forest are also within 3 miles (5 km).
 

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1862 Seasons on Main Bed and Breakfast

1862 Seasons on Main Bed and Breakfast

4.5 out of 5.0 47 Main Street, Stockbridge, MA
Situated in Stockbridge, this luxury bed & breakfast is within a 10-minute walk of Mission House and Berkshire Theatre Festival. Naumkeag and National Shrine of the Divine Mercy are also within 1 mile (2 km).
 
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Stockbridge Country Inn

Stockbridge Country Inn

4.5 out of 5.0 26 Glendale Road, RR 183, Stockbridge, MA
Situated in Stockbridge, this luxury bed & breakfast is within 1 mile (2 km) of Chesterwood and Norman Rockwell Museum. Berkshire Botanical Garden and Mission House are also within 2 miles (3 km).
 
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The Orchards Hotel

The Orchards Hotel

3.5 out of 5.0 222 Adams Rd, Williamstown, MA
3.8/5
(6 Reviews)
Situated in the mountains, this hotel is within 1 mi (2 km) of Hopkins Observatory and Williams College. Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts are also within 1 mile (2 km).
Reviewed on 23 Nov. 2019

There's an old-world elegance to the place. I'd liken it to visiting the home of an elderly, well-off grandmother. A place with faded glory.

 
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How much is a hotel room in The Berkshires?

Hotels in The Berkshires start at C$73 per night. Prices and availability subject to change. Additional terms may apply.

The Berkshires Hotel & Travel Guide

Are you on the hunt for a getaway that's truly away from it all? You can't go wrong with a trip to The Berkshires. With its abundance of lush forests, gently sloping hills, and cultural amenities, you'll be hard pressed to find a lovelier place. Choose from among many daily Albany flights to get there in no time, and get ready to explore all of Massachusetts' most magnificent wonders.

Out and About in The Berkshires

Start your tour of The Berkshires by enjoying the gorgeous scenery. To get the best views, climb Mount Greylock. If you can make it to the top, then congratulations! You'll be at the highest point in all of Massachusetts—take in breathtaking views of the dramatic landscape. After your trek, see fascinating exhibits at the Massachusetts Museum of Contemporary Art (MOCA). If art galleries aren't your thing, then be sure to stop by MoCA to check out the live events. Whether you're into theater, musical performance, or films, you're sure to find something you'll enjoy. Afterwards, head back to your The Berkshires hotel to unwind.

Eating and Drinking

Feeling a bit famished? Go to Great Barrington to find the highest concentration of great restaurants in The Berkshires. You'll find that most menus place an emphasis on serving up classic American comfort food. Go ahead and pig out on a burger and fries or some fresh lobster. If you're looking for the hippest bars, stick around Great Barrington. The bars here are cozy and small but offer innovative cocktails in an inviting atmosphere. Be sure to try out a frozen whisky lemonade. They're absolutely delicious. After a great night, rest up at any of the charming hotels in The Berkshires.

Ready to relax in style at the best hotels in The Berkshires? Thanks to Travelocity, it's never been easier to book your ideal getaway. You can search more than 510,000 hotels and 400 airlines to find the perfect vacation package to The Berkshires. You're sure to be enchanted on your holiday to rural Massachusetts.


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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.