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Lenox Vacation Packages

A dream destination for those who love all things artistic, this upscale town is known for hosting the world-famous Tanglewood Music Festival.

With stately mansions, five-star hotels, intriguing literary history and illustrious art venues, the town of Lenox stands out from its more modest Berkshires counterparts. Marvel at the grand summer homes of the elite and attend one of the music concerts held in the town. 

Enjoy a picnic on the lawn while listening to a live classical concert at Tanglewood, the famous summer home of the Boston Symphony Orchestra. The annual music festival has made Lenox an extremely popular destination in summer, so book your trip well ahead and expect high prices. The Jacob’s Pillow summer dance festival is also just a half-hour drive away in Becket. 

Glimpse lives of the super-rich who owned mansions in the area at the turn of the last century. Ventfort Hall was the summer "cottage" of Sarah Morgan, the sister of financier J.P. Morgan. Today, tour the lavish rooms and arrange to have a Victorian high tea on the grounds. Don’t miss the exhibits at the adjoining museum, showcasing the Berkshires as seen in that era, an exclusive mountain hideaway. 

The Blantyre offers a taste of turn-of-the-century glamor. Modeled after a Scottish castle, this former private mansion features eye-catching turrets and towers. It now functions as a luxury hotel. Visit the Italian garden or take a ghost tour at The Mount, the Lenox estate where Edith Wharton wrote The House of Mirth. Find many additional impressive homes downtown and along the beautiful winding country roads leading out of town.

Enjoy the surrounding countryside at the Pleasant Valley Wildlife Sanctuary, just a 10-minute drive from Lenox. From here start the hike up the green slopes of the 2,112-foot (644-meter) Lenox Mountain.

Find one-of-a-kind shops, cafés and restaurants contained within the few blocks of colonial buildings in the center of Lenox. You’ll need a car to reach the area and to explore the surroundings, but once here, the small town center is easily walkable. It’s also easy to get to Tanglewood on foot.


Top Hotel Deals

See all 102 Hotels in Lenox
£48
Days Inn Lenox MA

Days Inn Lenox MA

194 Pittsfield Rd, Lenox
3.1
of 5, from 96 reviews
2.0 out of 5.0

Situated in Lenox, this motel is within 2 mi (3 km) of Kennedy Park, Guido's Marketplace, and Pleasant Valley Wilderness Sanctuary. B.J. Faulkner Gallery and The Bookstore are also within 3 mi (5 km).

£92
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 111 reviews
2.5 out of 5.0

Situated in a rural location, this hotel is within 2 mi (3 km) of Guido's Marketplace, Arrowhead Museum, and Kennedy Park. Herman Melville's Arrowhead and Bousquet Ski Area are also within 2 mi (3 km).

£57
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
3.7
of 5, from 134 reviews
2.5 out of 5.0

Located in the heart of Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Guido's Marketplace, and Pleasant Valley Wilderness Sanctuary. Arrowhead Museum and B.J. Faulkner Gallery are also within 3 mi (5 km).

£46
Howard Johnson Express Inn - Lenox

Howard Johnson Express Inn - Lenox

462 Pittsfield Rd, Lenox
3.4
of 5, from 183 reviews
2.0 out of 5.0

Situated in Lenox, this motel is within 2 mi (3 km) of Guido's Marketplace, Arrowhead Museum, and Herman Melville's Arrowhead. Kennedy Park and Bousquet Ski Area are also within 2 mi (3 km).

£159
The Summer White House

The Summer White House

17 Main St, Lenox
3.0 out of 5.0

Situated in Lenox, this bed & breakfast is steps from Lenox Library, B.J. Faulkner Gallery, and The Bookstore. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 10 minutes.

£38
Wagon Wheel Inn

Wagon Wheel Inn

484 Pittsfield Rd, Lenox
3.6
of 5, from 68 reviews
2.0 out of 5.0

Located in the heart of Lenox, this motel is within 2 mi (3 km) of Guido's Marketplace, Bousquet Ski Area, and Arrowhead Museum. Herman Melville's Arrowhead and Kennedy Park are also within 2 mi (3 km).

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