Book Hotels in Winchester, Massachusetts

Wander wisely with the Travelocity Price Match Guarantee

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check hotel availability in Winchester

Tonight
Check prices in Winchester for tonight, Nov 30 - Dec 1
Tomorrow night
Check prices in Winchester for tomorrow night, Dec 1 - Dec 2
This weekend
Check prices in Winchester for this weekend, Dec 2 - Dec 4
Next weekend
Check prices in Winchester for next weekend, Dec 9 - Dec 11

Most frequently booked Winchester hotels

Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Winchester for Extended Stay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Seize your some day

Winchester Hotel & Travel Guide

Apartment and hotel choices are in abundance in Winchester. If you want to be within a 6-mile (10-kilometer) radius of Winchester, our comprehensive database contains at least 68 hotel options that match that criteria.

Read about many hotels you can stay at within a 3 miles (5 kilometers) drive from Winchester's downtown, including the Hyatt Place Boston/Medford and Hilton Boston/Woburn.

Have a look at the Mandarin Oriental Boston or the Four Seasons Hotel Boston. The Mandarin Oriental Boston is only 8 miles (13 kilometers) from the town center of Winchester. The Four Seasons Hotel Boston, is located just 8 miles (13 kilometers) away. The The Ritz-Carlton, Boston and also the Fifteen Beacon are alternative accommodation options worth looking into in Winchester.

The extended Eastern Massachusetts district is well worth seeing for yourself too. Explore Eastern Massachusetts's churches and art museums. Outdoorsy types should leave time to check out the region's coastal plains. Visitors in this pocket of United States of America adore snowboarding and skiing.

Cambridge is 5 miles (9 kilometers) south of Winchester and features Harvard Square and Harvard University. A few Travelocity-listed Cambridge hotels include the Fairmont Copley Plaza, Boston and The Charles Hotel. For another option, head to Natick, 16 miles (25 kilometers) to the southwest of Winchester, where you can choose from the Crowne Plaza Boston-Natick and Courtyard by Marriott Boston Natick. The Natick Collection and Cochituate State Park are some of the most popular sites to get to know in Natick.

During your vacation, spend a few hours enjoying the spectacle with some of Boston's spectators at a community game. Fenway Park is 8 miles (12 kilometers) to the south of Winchester. Anybody hoping to find a room or apartment near to the sporting action can compare between the Marriott Vacation Club Pulse at Custom House, Boston or the The Colonnade Hotel Back Bay.

Logan International Airport is 9 miles (14 kilometers) away from Winchester's urban core. Enlightened travelers who choose to find a room nearby can look into a convenient option in the InterContinental Boston or Kimpton Nine Zero Hotel.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
Family trips are where amazing memories are made, but it’s no secret that traveling with youngsters can be challenging. These kid-friendly Winchester hotels come with perks that aim to keep young and old alike relaxed and happy: The whole gang will enjoy staying at 6 BR Home - 15 minutes to Harvard, Longwood, Tufts, MIT. Beach sun loungers and a nearby theme park are among the things that help make this hotel an appealing option. Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93 is another top pick. After an exciting day of sightseeing, return to your comfy room and amenities like nearby hiking and a nearby theme park.
Where can I find cheap hotels in Winchester?
At Travelocity you’ll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we’ve already found in Winchester then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $104. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 2501 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during . If you’d prefer the peace of off-season, book a stay during quieter months, such as .
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We’ve got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers