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USA

Boston - Northampton - The Berkshires (Self Drive)

6 to 9+ Nights from $1,673*
* Sample price: priced within the past 7 days for a 7/29/2025 arrival, departing Miami MIA (FL), US. Choose departure city, cabin and dates.

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Add Outbound & Return Flights

This 6 night sample itinerary includes:

  • Flight into Boston and out of Albany
  • Rental Car for 6 days
  • Hotel for 2 nights in Boston
  • Hotel for 2 nights in Northampton
  • Hotel for 2 nights in The Berkshires
  • Driving Time
    Boston– Northampton: 1 hr 42 min approx.
    Northampton– The Berkshires: 1hr 3 min approx.
    The Berkshires– Albany: 1hr 2 mins approx.

With this vacation package you will visit exciting cities in Massachusetts and New York. Combine Boston (One of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), Northampton and The Berkshires (A popular vacation destination, known for outdoor activities, colorful fall and thriving arts institutions); with a rental car.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • Boston, MA

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  • Northampton, MA

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  • The Berkshires, MA

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USA

Customer Reviews

Trip Summary

  • Boston, MA
    Boston, MA

    Whether you are looking to take in the skyline or enjoy art, visit a museum or spend the day getting pampered, you will find what you want in Boston. Laced with parks, and pathways you can easily take in the skyline, while enjoying walking the Greenway, Harborwalk, Esplanade or Freedom Trail.

    Explore The Freedom Trail, the Museum of Fine Arts, the Faneuil Hall Marketplace, the Boston Tea Party Ships & Museums, the Boston Public Garden and so much more!

  • Northampton, MA
    Northampton, MA

    Northampton is a city in the Pioneer Valley of Massachusetts with a picturesque and vibrant downtown, consisting of numerous art galleries, restaurants and quirky shops sprinkled among coffee shops and performing arts venues. The city is nationally known for being a bohemian college town and LGBT mecca.

    Explore The Look Memorial Park, the Botanic Garden of Smith College, the Smith College Museum of Art, the Skinner State Park, the Mount Holyoke, the Norwottuck Rail Trail, the Metacomet-Monadnock Trail, the Calvin Coolidge Presidential Library and Museum and so much more!

  • The Berkshires, MA
    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!

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