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The Berkshires are home to an impressive collection of cultural and historic sights. Get your fill of music, art and theater at Tanglewood, the Boston Symphony's summer home, MASS MoCA, the country's largest contemporary art center, the Norman Rockwell Museum and the Williamstown Theatre Festival. Recreational opportunities also abound, including snowshoeing, snowboarding, skiing, rafting, kayaking, fishing and golf. The Berkshires are an easy drive, just two and a half hours from Boston and... more » The Berkshires are home to an impressive collection of cultural and historic sights. Get your fill of music, art and theater at Tanglewood, the Boston Symphony's summer home, MASS MoCA, the country's largest contemporary art center, the Norman Rockwell Museum and the Williamstown Theatre Festival. Recreational opportunities also abound, including snowshoeing, snowboarding, skiing, rafting, kayaking, fishing and golf. The Berkshires are an easy drive, just two and a half hours from Boston and New York. « less
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192 Hotels & Accommodations

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Reviews you can trust

“Very comfortable feeling- Liked It”

Wyndham at Bentley Brook

4 of 5 stars
roonyann
New York
Nov 22, 2009

We stayed for almost a week in November. We were looking for a comfortable place to be our base as we did things in the area. The place was great. The unit was very comfortable and quite clean. ...more

“If there are no spaces out front - keep going - DREADFUL service”

Sullivan Station Restaurant

2 of 5 stars
roonyann
New York
Nov 22, 2009

We had been to this restaurant a few times a couple of years back while we were in the area on vacation. We decided to try it on 11/11/09 for lunch, which was Veteran's Day. They only have limited...more

“Yummy Italian food, especially to this very picky Italian eater!”

Frankie's Ristorante Italiano

5 of 5 stars
kiwi28104
New York, NY
Nov 22, 2009

We've been to Frankie's several times over the last two summers, during our trips to the Berkshires. We've yet to try something that we didn't ultimately love. The pasta is cooked perfectly (never...more

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Lee MA into CT on Rt 8 October 31, 2009, 1 reply
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Don't go to the Ventfort Hall October 15, 2009, no replies
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Destinations of the Day
Miami Beach, Florida
  • Resident population: 87,925 Annual visitors: 10,000,000 (est.)
  • Major features: nightlife, beaches, shopping, art museums
  • 25,680 TripAdvisor reviews of 353 accommodations, 69 attractions and 399 restaurants
South Beach, or SoBe, is Miami Beach's buzziest bit. The vibrant area, with its pastel-hued buildings, hip nightclubs, trendy shops and see-and-be-seen restaurants, attracts socialites and their satellites year-round.
Phuket, Thailand
  • Resident population: 320,000 Annual visitors: 5,000,000 (est.)
  • Major features: beaches, water sports, golf courses, nightlife, temples
  • 16,311 TripAdvisor reviews of 755 accommodations, 88 attractions and 164 restaurants
Phuket offers a rainbow spectrum of spectacular vacation sights from blue lagoons and pink sunsets to orange-robed monks.
Tenerife, Spain
  • Resident population: 852,945 Annual visitors: 3,440,000 (est.)
  • Major features: beaches, parks, water sports, golf courses
  • 23,576 TripAdvisor reviews of 658 accommodations, 132 attractions and 781 restaurants
Strongly influenced by the tribal culture of the Guanches (the original inhabitants), Tenerife was conquered by the Spanish 500 years ago.
Jamaica
  • Resident population: 2,825,928 Annual visitors: 1,704,000 (est.)
  • Major features: beaches, scuba diving, cliff diving, jungle tours
  • 50,042 TripAdvisor reviews of 1,260 accommodations, 260 attractions and 305 restaurants
Jamaica is a melting pot of African, Asian, European and Middle Eastern cultures. You'll experience this diversity in its strong crafts tradition, performing arts and distinctive dining options, like ackee and saltfish with roast breadfruit.
Koh Samui, Thailand
  • Resident population: 47,874 (est.)
  • Major features: beaches, water sports, ecotourism
  • 8,979 TripAdvisor reviews of 431 accommodations, 43 attractions and 75 restaurants
Luxury resorts rub elbows with backpacker accommodations on the Thai island of Ko Samui, a 15-mile-long palm-covered tropical oasis located off the country's east coast.