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.
Skyline of Boston
The art of stones... was it natural or by man? Doesn't matter as long as it attracted my attention. Art is abstract!!! #hiking
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
$194 nightly
The price is $226 total per night from Apr 5 to Apr 6
$226 total
Apr 5 - Apr 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! (4,541 reviews)
PERFECT

Reviewed on Mar 24, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
$182 nightly
The price is $212 total per night from Apr 5 to Apr 6
$212 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this luxury hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (3,133 reviews)
Best hotel experience I’ve ever had. The complementary waters made all the difference. Having access to an awesome gym was also amazing for people who enjoy fitness and gyms while traveling.

Reviewed on Mar 24, 2026

Hilton Boston Park Plaza
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$165 nightly
The price is $192 total per night from Apr 5 to Apr 6
$192 total
Apr 5 - Apr 6
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! (4,092 reviews)
Room was clean. Bathroom sink was not draining well. Took 40 minutes to get our car, which made us late for an appointment. On arrival was told we had a $30 credit from Expedia to use for breakfast or dinner at the restaurant. We decided to have breakfast but was charged $75.00. After several phone ...

Reviewed on Mar 24, 2026

Seaport Hotel Boston
See all 4,138 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 New England Aquarium are ...
7.2/10 Good! (341 reviews)
The apartment was very clean and the location very convenient to shopping, the Commons and there’s a great cafe right across the street. The kitchen was fairly well equipped except my unit only had 2 spoons. One improvement would be the addition of some dish towels in the kitchen. I had a great stay ...

Reviewed on Mar 25, 2026

Temple Place Suites
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! (672 reviews)
Large room with full kitchen and living room

Reviewed on Mar 24, 2026

Global Luxury Suites Downtown Boston
Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston

3.5 out of 5
3 Mckinley Square Boston MA
Stay at this condo in Boston. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (623 reviews)
Hotel is in the perfect area to go to Faneuil hall as well as to the north end everything’s in walking distance multiple restaurants you can eat high-end or very inexpensive fun time for all

Reviewed on Mar 10, 2026

Marriott Vacation Club® at Custom House, Boston
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

Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts

Fenway Park

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

Fenway Park
Historic architecture of Harvard University in Cambridge, Massachusetts under clear blue skies

Harvard University

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 showcases lush greenery and city skyline under a clear blue sky during a sunny day

Boston Common

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's Zakim Bridge

TD Garden

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
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

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

Gillette Stadium
New England Aquarium featuring marine life

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
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
100% 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

$56
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
Odyssey Boston Premier Elegant Dinner Cruise

City Cruises Boston: Premier Elegant Dinner Cruise

$146
per adult
72% of travellers recommend
City Cruises Boston: Premier Elegant Dinner Cruise
Museum of Ice Cream Boston Admission Ticket

Museum of Ice Cream Boston Admission Ticket

$44
per adult
Museum of Ice Cream Boston Admission Ticket
See all activities in Winchester

Cities near Winchester

Revolutionary War memorial in winter, Lexington, Massachusetts

Lexington

Cold but sunny A day out stretching my lazy legs..... 🚶🏻‍♀️🚶🏻‍♀️🚶🏻‍♀️🚶🏻‍♀️

Medford

Woburn showing street scenes and an administrative buidling

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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