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Berkshires and Hudson Valley (Self Drive)

6 to 9+ Nights from $409*
* This sample price: priced within the past 7 days for check-in on 3/2/2025. Choose your own arrival dates.

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This 6 night sample itinerary includes:

  • Rental Car for 5 days
  • Hotel for 1 night in Worcester
  • Hotel for 2 nights in Lenox
  • Hotel for 1 night in Beacon
  • Hotel for 2 nights in New York City
  • Driving Time
    Boston – Worcester: 1 hr approx.
    Worcester – Lenox: 1 hr. 35 mins approx.
    Lenox – Beacon: 1 hr. 45 mins approx.
    Beacon – New York City: 1 hr. 35 mins. approx.

This Self-Drive package through Massachusetts and New York States is great option for those looking to get off the beaten path and take their own time. Combine Worcester (best known for its magnificent Cathedral, also famous for the world renowned Worcester Porcelain, the piquant Worcestershire Sauce and the most picturesque cricket ground in the country)and Lenox in the beautiful Berkshires Area. After that, drive to The Empire State, spending glorious days in Beacon (noted for its proximity to numerous historic sites and large cities and for its creativity, art and culture) and finally, visit the capital of the world; New York City (a city where to enjoy its world-class museums, amazing food and entertainments). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Flexible Itinerary

  • Worcester, MA

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  • Lenox, MA

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  • Beacon, NY

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  • New York City, NY

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Trip Summary

  • Worcester, MA
    Worcester, MA

    Worcester (pronounced Wuss-ter) is the largest city in central Massachusetts and is a noteworthy commercial and cultural hub between Boston and The Berkshires. Nicknamed `The Heart of the Commonwealth`, Worcester is known for its gorgeous Victorian and Colonial-era buildings as well as museums such as the American Antiquarian Society, the Worcester Art Museum, the Worcester Historical Museum, and the EcoTarium.

    Explore The Worcester Art Museum, the Tower Hill Botanic Garden, the EcoTarium, the Ski Ward Ski Area, the Wachusett Reservoir, the Mass Audubon`s Broad Meadow Brook Conservation, the Green Hill Park, the Elm Park Center and so much more!

  • Lenox, MA
    Lenox, MA

    A short walk from the inn will find you in the historic village of Lenox, the heart of culture in the Berkshires. Shop the appealing boutiques, discover antique treasures and fine art in its many galleries, and dine in the town`s splendid restaurants. The Lenox Library is a historic landmark, hosted in a 200-year-old courthouse building since 1874.

    Explore The Tanglewood, The Mount, Edith Wharton's Home, Pleasant Valley Sanctuary, Ventfort Hall Mansion and Gilded Age Museum, Shakespeare & Company, Kennedy Park and so much more!

  • Beacon, NY
    Beacon, NY

    Just thirty minutes from Poughkeepsie in the Hudson River Valley sits the city of Beacon, situated just across the Hudson from its sister city, Newburgh. It is a gateway town to the Canopus Beach Complex, a popular lakeside beach destination, and to Hudson Highlands State Park. Walk to the top of Breakneck Ridge where you can catch a breathtaking view of the Hudson, Pollepel Island, and the abandoned military fortification there called Bannerman`s Castle.

    Visit the Dia:Beacon, Beacon Mountain, Breakneck Ridge, Pollepel Island, Bannerman`s Castle, Long Dock Road, Hudson Highlands State Park, Madam Brett Homestead Museum, and so much more!

  • New York City, NY
    New York City, NY

    New York City, the Big Apple, is the USA's largest city. Founded as New Amsterdam, the capital of New Netherland, it became the most important city in the English colonies, and the USA`s first capital. New York City is the world capital of finance, media, and culture, and is perhaps the world`s most diverse city, where over 800 languages are spoken. There are so many layers to the city that never sleeps...you'll have to come back again and again to experience all of them.

    Visit and vibe with the Central Park, Statue of Liberty, Empire State Building, Times Square, Museum of Modern Art (MoMA), Metropolitan Museum of Art, Brooklyn Bridge, Rockefeller Center, The High Line, Grand Central Station, One World Trade Center, Fifth Avenue, Broadway, and so much more!

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