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44 Travelers rated Winchester highly for Soccer and Family-Friendly

Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
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Book a package and join the 188 others who’ve received 100% off their flights this year!

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Top Rated Hotels for your Winchester Vacation

Boston Park Plaza
Boston Park Plaza
4.0 out of 5.0 50 Park Plaza at Arlington Street, Boston, MA
Free Cancellation
$94
4.2/5 (226 reviews)

convenient to the theatre, to the restaurants, to China Town,

Reviewed on Dec 2, 2019
Located in Back Bay, this historic hotel is within a 10-minute walk of Newbury Street, Boston Public Garden, and Boston Common. Copley Place and Hynes Convention ...
Boston Omni Parker House Hotel
Boston Omni Parker House Hotel
4.0 out of 5.0 60 School St, Boston, MA
Free Cancellation
$105
4.2/5 (145 reviews)

Very nice staff and beautiful historic property. Would stay again.

Reviewed on Dec 8, 2019
Located in Downtown Boston, this historic hotel is within a 10-minute walk of Boston City Hall, Quincy Market, and Boston Common. New England Aquarium and Boston ...

Tips for planning your Winchester vacation

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Join Orbitz Rewards

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 $420^!

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?

Join Orbitz Rewards

Want really, really fast rewards? All you have to do is continue booking with us and you'll gain Orbucks! It's an easy system we've come up with to reward you, lightning fast!

Obtain gold or platinum status for special perks at Orbitz Rewards VIP Hotels. How? Just book four nights for gold and 12 nights for platinum in a year. And how do you redeem Orbucks? It's easy — just make use of your Orbitz Rewards points on your next booking.

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.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.