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Brattleboro - The Berkshires - Hudson - New York City (Self Drive)

8 to 12+ Nights from $990*
* This sample price: priced within the past 7 days for arrival on 9/1/2024. Choose your own arrival dates.

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This 8 night sample itinerary includes:

  • Rental Car for 9 days
  • Pick up in Manchester and drop off first day of NY
  • Hotel for 2 nights in Brattleboro
  • Hotel for 2 nights in The Berkshires
  • Hotel for 2 nights in Hudson
  • Hotel for 2 nights in New York City
  • Driving Time
    Manchester – Brattleboro: 1 hr 35 min approx.
    Brattleboro - The Berkshires:1hr 39 min approx.
    The Berkshires- Hudson: 1hr 1 min approx.
    Hudson - New York City: 2hs 22 min approx.

Venture through these beautiful cities of Vermont, Massachusetts and New York State enjoy its natural landscapes and nightlife with a rental car. Explore the beautiful city of Brattleboro (the city is easily Accessible From Everywhere, with great outdoors activities and a main street full of shops and restaurants), The Berkshires, Hudson and New York City (one of the world's largest entertainment capitals; with world-class museums, amazing food and shows). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.

Flexible Itinerary

  • Brattleboro, VT

  • The Berkshires, MA

  • Hudson, NY

  • New York City, NY

Customer Reviews

Trip Summary

  • Brattleboro, VT

    Brattleboro, originally Brattleborough, is a city in Windham County, Vermont. The town operates and maintains the Gibson-Aiken Center, a large recreation and community activities facility, located downtown on Main Street, along with a number of parks and outdoor recreation centers, including Living Memorial Park, whose features include an outdoor swimming pool and a municipal skiing facility.

    Explore The Madame Sherri Forest, the Retreat Farm, the Wantastiquet Mountain Natural Area, the Fort Dummer State Park, the Brattleboro Historical Society, the Vermont Center for Photography and so much more!

  • The Berkshires, MA

    The Berkshires boast over 100 cultural attractions, many of which are world-renowned. The region is surrounded by picturesque mountains in a lush green valley, where you will find numerous, unique recreational activities and festivals that run throughout the year.

    Explore The Ski Butternut, the Otis Ridge, the Beartown State Forest, the Monument Mountain Reservation, the Ski Blandford, the Tolland State Forest and so much more!

  • Hudson, NY

    Hudson is located on the Hudson River between Albany and Poughkeepsie. It is known for its historic district, which spans 45 city blocks and consists of a variety of architectural styles from the 18th to early 20th centuries. Once known as a town with legalized gambling and prostitution, today it is renowned for some of the best antiques shopping you can find in the Northeast, and a burgeoning LGBTQ community, many of whom are transplants from New York City.

    Explore the Olana State Historic Site, Hudson-Athens Lighthouse, Fireman`s Firefighting Museum, Warren Street, Thomas Cole National Historic Site, Henry Hudson Riverfront Park, Rip Van Winkle Bridge, Cornelius H. Evans House, and so much more!

  • 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'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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