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Boston - Concord - Woodstock - Manchester (Self Drive)

6 to 9+ Nights from $2,121*
* Sample price: priced within the past 7 days for a 9/16/2025 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 Manchester
  • Rental Car for 7 days
  • Hotel for 2 nights in Boston
  • Hotel for 1 night in Concord
  • Hotel for 2 nights in Woodstock
  • Hotel for 1 night in Manchester
  • Driving Time
    Boston– Concord: 1 hr 4 min approx.
    Concord – Woodstock: 1hr 21 min approx.
    Woodstock – Manchester: 1hrs 32 mins approx.

Self-drive packages through Massachusetts, New Hampshire and Vermont are a popular option for more experienced travelers, those looking to get off the beaten path and take their own time. Combine Boston (One of the oldest and populous cities of Massachusetts, famous for its baked beans and the Boston Marathon), Concord, Woodstock and Manchester (A town in southern Vermont and a true all season destination with an upscale outlet shopping).

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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  • Concord, NH

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  • Woodstock, VT

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  • Manchester, NH

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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!

  • Concord, NH
    Concord, NH

    Concord is the capital city of New Hampshire. In the 19th century, Concord became a hub for the railroad industry, with Penacook a textile manufacturing center using water power from the Contoocook River. The city is home to the State House, a gold-domed building dating from 1819, with a visitor center and the Hall of Flags.

    Explore The McAuliffe-Shepard, the Canterbury Shaker Village, the Bear Brook, the New Hampshire State House, the Chuckster`s, the NH Audubon, the New Hampshire Historical Society and so much more!

  • Woodstock, VT
    Woodstock, VT

    Named the `quintessential New England village,` the town of Woodstock is chock full of charming Americana, including a covered bridge smack in the center of town and a village green surrounded by restored Georgian, Federal Style and Greek Revival homes.

    Explore The Billings Farm and Museum, the Marsh-Billings-Rockefeller National Historical Park, the Suicide Six, the Calvin Coolidge Historic Site, the Sugarbush Farm, the Mount Tom and so much more!

  • Manchester, NH
    Manchester, NH

    Manchester is a city on the Merrimack River in southern New Hampshire. Manchester is most known for its history with the mills. Many buildings surrounding the Merrimack River, which run through the center of the city, are old mill buildings.

    Explore The Northeast Delta Dental Stadium, the Zimmerman House, the Studio 550 Art Center, the SEE Science Center, the Massabesic Lake, the Palace Theatre, the Millyard Museum, the Firefly American Bistro & Bar and so much more!

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