Winchester, MA

Travel Guide

Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.
Aerial view of Winchester Center Historic District and First Congregational Church panorama in downtown Winchester, Massachusetts, USA.
Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA.
Winchester
Winchester
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$202 nightly
The price is $234 total per night from May 10 to May 11
$234 total
May 10 - May 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (4,300 reviews)
Excellent

Reviewed on May 8, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
$225 nightly
The price is $262 total per night from May 10 to May 11
$262 total
May 10 - May 11
Total with taxes and fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (4,641 reviews)
Great location. Nice modern room.

Reviewed on May 8, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$135 nightly
The price is $157 total per night from May 10 to May 11
$157 total
May 10 - May 11
Total with taxes and fees
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,602 reviews)
The location was perfect. Super fun hotel. Would absolutely stay here again

Reviewed on May 8, 2026

The Revolution Hotel
See all 4,205 properties in Winchester
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.
Temple Place Suites

Temple Place Suites

2.5 out of 5
29 Temple Place Boston MA
Stay at this apartment in Boston. Enjoy free WiFi, laundry facilities, and cable TV channels. Popular attractions Boston Common and Faneuil Hall Marketplace ...
7/10 Good! (368 reviews)
The maintenance of the room was very poor: stains, rust, dust, wobbly taps and towel racks, old paint, etc. Cleanliness: stains on carpet, dust everywhere, long hairs on pillows. Upon check in the room was organized, but no deep cleaning was apparent.

Reviewed on May 5, 2026

Temple Place Suites
Crescent Suites Hotel

Crescent Suites Hotel

3 out of 5
287 Crescent Street Waltham MA
Book a stay at this business-friendly aparthotel in Waltham. Enjoy a fitness center, a business center, and a garden. Our guests praise the helpful staff and ...
9.6/10 Exceptional! (1,188 reviews)
Good location, clean, good condition and room set up

Reviewed on May 9, 2026

Crescent Suites Hotel
Premier Suites - Bay Village

Premier Suites - Bay Village

2 out of 5
1-3-5 Cortes Street Boston MA
Stay at this aparthotel in Boston. Enjoy free WiFi and laundry facilities. Popular attractions Copley Square and Boston Common are located nearby.
6.2/10 (275 reviews)
It was a nice room and pretty close to things to do.

Reviewed on May 8, 2026

Premier Suites - Bay Village
See all properties in Winchester
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.

Popular places to visit

Fenway Park

Fenway Park

4.5/5(2,543 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(1,983 reviews)

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

Harvard University
Boston Common

Boston Common

4.5/5(4,846 reviews)

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.

Boston Common
Gillette Stadium

Gillette Stadium

4.5/5(400 reviews)

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Gillette Stadium
Boston's Zakim Bridge

TD Garden

4.5/5(1,818 reviews)

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

TD Garden
Copley Square

Copley Square

4.5/5(643 reviews)

Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax.

Copley Square

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$46
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

$28
per adult
LEGO Discovery Center Boston Admission Ticket
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

$54
per adult
98% of travellers recommend
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions
See all activities in Winchester

Cities near Winchester

Revolutionary War memorial in winter, Lexington, Massachusetts

Lexington

Historic Kirby Mill, circa 1778, Medford, New Jersey

Medford

Woburn

Woburn

Arlington Heights suburban landscape panoramic aerial view in spring with Spy Pond and Boston modern city skyline at the background in historic town of Arlington, Massachusetts MA, USA.

Arlington

Explore a world of travel with Expedia