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
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $167 total per night from Jun 30 to Jul 1
$167 total
Jun 30 - Jul 1
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 ...
The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
$177 nightly
The price is $205 total per night from Jul 19 to Jul 20
$205 total
Jul 19 - Jul 20
Total with taxes and fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant ...
9/10 Wonderful! (2,384 reviews)
"My Favorite Boston Hotel. Affordability w 5 star services. Balcony rooms are my go to : )"

Reviewed on Jun 24, 2026

Hyatt Regency Boston/Cambridge
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
$242 nightly
The price is $282 total per night from Jul 5 to Jul 6
$282 total
Jul 5 - Jul 6
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! (4,736 reviews)
"Clean room and excellent facilities. It’s maybe a bit far from the centre, but otherwise we couldn’t fault it."

Reviewed on Jun 24, 2026

Omni Boston Hotel at the Seaport
See all 4,165 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.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
8 Harrison Ave Boston MA
Book a stay at this business-friendly aparthotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a 24-hour business center. Our guests praise the helpful ...
8/10 Very Good! (710 reviews)
"Good location and convenient to Chinatown. Would have liked more than 1 hand towel and bath towel (no washcloths) for a 4-night stay but they provided laundry detergent and in-unit laundry was a plus. Having a microwave, tea kettle, and refrigerator was nice too. Comfortable bed and good safety features ..."

Reviewed on Jun 24, 2026

Global Luxury Suites Downtown Boston
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 New England Aquarium are ...
7/10 Good! (396 reviews)
"UNA ESTANCIA LIMPIA Y MUY SILENCIOSA TODOFUE EXCELENTE!!"

Reviewed on Jun 21, 2026

Temple Place Suites
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.
6.4/10 (294 reviews)
"Au centre ville bon rapport qualité prix on a marché fenway parc et TD garden environ 30 minutes chaque de notre chambre seul point a prendre en considération est la salle de bain partagé bien que ça n’a pas été un problème pour nous j’y retournerais bien !"

Reviewed on Jun 21, 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
Gillette Stadium

Gillette Stadium

4.5/5(400 reviews)

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

Gillette Stadium
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'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
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
Boston Harbor

Boston Harbor

4.5/5(732 reviews)

Adore Boston’s charming working harbor from the waterfront or head out by boat to get to know it more intimately.

Boston Harbor

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
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
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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

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