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Most Frequently Booked The Berkshires Hotels

C$160
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 within 9 miles (15 km) of Mount Greylock State Reservation Visitor Center, Pittsfield State Forest and Waubeeka Golf Links. New Lebanon Library and Mount Lebanon Shaker Village are also within 12 miles (20 km).
C$138
The Red Lion Inn

The Red Lion Inn

3.5 out of 5.0 30 Main Street, Stockbridge, MA
3.9/5
(7 Reviews)
Situated in the historical district, this historic hotel is within a 10-minute walk of Mission House and Berkshire Theatre Festival. Naumkeag and National Shrine of the Divine Mercy are also within 15 minutes.
C$130
Holiday Inn & Suites Pittsfield-Berkshires

Holiday Inn & Suites Pittsfield-Berkshires

3.5 out of 5.0 One West Street, Pittsfield, MA
3.6/5
(22 Reviews)
Located in the heart of Pittsfield, this spa hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater and Berkshire Athenaeum. Canoe Meadows Wildlife Sanctuary and Arrowhead Museum are also within 3 miles (5 km). Pittsfield Intermodal Transportation Center is 6 minutes by foot.

Top Cheap The Berkshires Hotel Deals

C$79
Lantern House Motel

Lantern House Motel

2.5 out of 5.0 256 Stockbridge Road, Great Barrington, MA
4.4/5
(17 Reviews)
Situated in the mountains, this motel is 1.8 mi (2.9 km) from Lake Mansfield Park and 2.6 mi (4.2 km) from Ski Butternut. Mahaiwe Performing Arts Center and Beartown State Forest are also within 3 miles (5 km).
 
C$66
Wagon Wheel Inn

Wagon Wheel Inn

2.0 out of 5.0 484 Pittsfield Rd, PO Box 808, Lenox, MA
3.2/5
(8 Reviews)
Located in the heart of Lenox, this motel is within 2 miles (3 km) of Arrowhead Museum, Bousquet Ski Area and Kennedy Park. Canoe Meadows Wildlife Sanctuary and Pleasant Valley Wilderness Sanctuary are also within 3 miles (5 km).
 
C$57
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).
 

Top Luxury The Berkshires Hotel Deals

C$156
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).
 
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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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How much is a hotel room in The Berkshires?

Hotels in The Berkshires start at C$57 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.


Recent The Berkshires Hotel Reviews By Fellow Wanderers

*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.