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The Lenox Hotel Boston
Fairmont Copley Plaza, Boston
Mandarin Oriental, Boston
The Langham, Boston
Raffles Boston

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Winchester Vacations

Are you set for your next unforgettable adventure? Ensure you don't miss out on any fun in Winchester by learning the basics about it before you jet off.

This town is 2 miles (3 kilometers) away from Woburn and 3 miles (5 kilometers) away from Stoneham.

The population of this area of Massachusetts is nearly 21,000.

Places to visit in Winchester

This town provides easy access to some excellent attractions. The Harvard University and the Semitic Museum are well worth taking a look at, so add them to your travel schedule and find out if you've got time to get to all of them.

If you want to see where the locals do much of their shopping, visit Harvard Square. Have a wander around and check out which stores they frequent the most. Want more options? Traveling can often mean wearing the same clothes day in, day out. So, if you fancy treating yourself to a snazzy new outfit, make your way over to Burlington Mall. But that's not all. If you're dying to see where the local people go to do their shopping, drop by Square One Mall. Have a look around and discover which stores they frequent the most.

Where do you fly into for Winchester?

When you're planning your upcoming Winchester trip, keep in mind that the closest airport, Logan International Airport (BOS), is about 9 miles (14 kilometers) to the southeast of the downtown area. Book your flights, pack your luggage and prepare for some awesome adventures!

Frequently asked questions

How much are vacation packages to Winchester?
Treat yourself to a memorable travel experience in Winchester with a vacation package starting at just CA $897. Reserving your flights, hotels and tours with Travelocity is so simple. And even better, our great deals will leave you with extra cash for fun.
Where can I get the best vacation package deals for Winchester?
You can pick up awesome Winchester package deals with Travelocity. Select from as many as 400 partner airlines and 1,000,000 properties worldwide and turn your travel dreams into reality.
Why should I purchase my Winchester vacation package via Travelocity?
You’ll not only enjoy big savings, but you’ll also have access to our 24/7 support, high-quality service and a Price Match Guarantee. Wander across the world, discover hidden sights and make lifelong memories — we’ll take care of the important details.
Can I save on my Winchester car rental if I bundle it with hotels and flights?
Combining your hotel, flight and car into a Winchester vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you freedom to get to all those famous sights you want to see. Sitting 64 kilometers away from Winchester, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.
Which airport is best for Winchester?
Many people fly into Logan Intl. Airport (BOS), 14 kilometers southeast of downtown Winchester. Others prefer T.F. Green Airport (PVD) (88 kilometers away from central Winchester) or Manchester-Boston Regional Airport (MHT) (56 kilometers away from central Winchester).
What is there to do in Winchester?
Snap up the excellent photo-ops at Winter Pond, one of the most well-known attractions in Winchester. There’s plenty more to uncover in this exciting destination, so give yourself enough time to visit some of its hidden gems.
Where should I stay when visiting Winchester?
Many people spend their nights at the Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93. It’s sure to be a good base for your Winchester getaway.

Photos of local treasures

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