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Winchester Travel Guide

On the hunt for amazing-value Winchester bargains? Save time and cash by letting the brilliant team at Orbitz bundle up your hotels and flights.

Bundling your bookings is a perfect way to save money. Choose your desired hotels, rental cars, airfares and experiences for savings of up to !

What's more, our database lists no less than 500,000 hotels across the globe and 500 partner airlines. Don't stress out if you have trouble selecting the right ones — we'll make it a breeze!

There are countless flight options, room types and incredible experiences to satisfy your wandering spirit. Which ones will you go for?

Winchester Travel Guide

Where is Winchester?

The boss has signed off your annual leave, work friends have recommended Winchester and you just need a little reminder of where it actually sits on the map? Sit back and let us guide you there.

If you take a trip 2 miles north of Woburn, or 3 miles southwest of Stoneham, you'll be in Winchester.

Eager to mingle with the locals? That shouldn't be too difficult. 21,000 people call this area of Massachusetts home.

Places to Visit in Winchester

Don't pack your bags without having a squiz at some of the area's most popular attractions, like the Harvard University and the Semitic Museum.Spend the day shopping at Harvard Square where you can buy the perfect souvenirs to take back home. Need some more options? Shop up a storm, run some errands or just sit back with a drink at Burlington Mall, a popular shopping destination for travelers and locals alike. Hold up, there's still more! Square One Mall is among the best shopping centers in the area and an excellent place to carry out some retail therapy.

Car Rentals in Winchester

Adventure is fuel for the soul, and there’s no better way to find it than with the freedom of your own wheels. See and experience more by checking out car rentals in Winchester with the help of Orbitz.

There's no reason to waste time figuring out the best way into town. Pick up a car from the Logan International Airport area and save yourself the stress. Check out Advantage Rent-A-Car and Enterprise.

Head on over to Enterprise and you'll be cruising around the busy streets in a jiffy. They are located at 4 Dudley Place, a mere 2 miles from the town center.

Where to stay in Winchester – Hotel Accommodation

Lock in your hotel in Winchester with Orbitz right now! There are 65 listed options in this awesome destination, so securing a nice room will be a breeze.If something a little extravagant is what you're longing for, slip between the silky sheets at the Global Luxury Suites at Kendall East or the Global Luxury Suites at General. Alternatively, check out the Harvard Square Hotel and the Days Hotel-Boston/Cambridge. These are some of our top budget hotels.

Nearest Airports to Winchester

Your adventure kicks off the moment you step out of the cabin at Logan International Airport (BOS). Situated 9 miles southeast of the downtown area, this is Winchester's main terminal.

Popular Places to Visit Near Winchester

Winchester has an abundance of things to keep you busy, but if you'd like to branch outwards, you're in luck! You've got globally celebrated tourist attractions close at hand! 40 miles away is Duxbury. Many visitors use this destination as a base to visit the world-famous attraction, the Plymouth Rock.

No Cancellation Fees

Need to cancel or alter your booking? Worried about getting hit with a fee? Well, you'll be relieved to learn that we don't have one!^ Touch wood, your chosen airline and hotel don't either, but it's a good idea to get in touch with them regarding their rules.

Top rated hotels for your Winchester vacation

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