
Winchester Vacations from $542
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Your Winchester Vacation
Book a Winchester vacation package that includes everything you need and nothing you don't. Great for nightlife, shopping and bars and pubs, consider staying in the neighborhood of Downtown Boston. A trip to Winchester is a terrific opportunity to see the sights. Be sure to look around renowned attractions like Harvard Square, Harvard University and Bentley College. Stop dreaming and start traveling. Browse the broad range of options on Expedia today and finally put your Winchester vacation plans into gear!
The Latest Winchester vacation packages


Embassy Suites Boston Logan Airport
Reviewed on Jul 6, 2025

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Reviewed on May 8, 2025


Ocean Air Suites
Reviewed on Sep 3, 2024
Discover the most popular places to visit in Winchester

Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Boston Common
The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.
What to do in Winchester

Boston CityPASS®: Admission to Top 4 Attractions

Liberty, Freedom, and Revolution: American History Tours Bundle
Winchester Hotel Deals

Reviewed on Jul 6, 2025

Reviewed on Jul 3, 2025

Reviewed on Jul 5, 2025
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Logan Intl. Airport (BOS) |
Population | 21,400 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | New England Aquarium, Boston Museum of Fine Arts and Revere Beach |
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