Winchester, MA

Travel Guide

Winchester Town Hall and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.
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
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
$139 nightly
The price is $162 total per night from Feb 19 to Feb 20
$162 total
Feb 19 - Feb 20
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 ...
8.2/10 Very Good! (3,117 reviews)
Location

Reviewed on Feb 6, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$119 nightly
The price is $139 total per night from Feb 16 to Feb 17
$139 total
Feb 16 - Feb 17
Total with taxes and fees
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. ...
9.2/10 Wonderful! (6,199 reviews)
Best price for the location! Always clean and great staff!

Reviewed on Feb 4, 2026

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$81 nightly
The price is $95 total per night from Feb 9 to Feb 10
$95 total
Feb 9 - Feb 10
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! (2,450 reviews)
I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would ...

Reviewed on Feb 7, 2026

The Revolution Hotel
See all 4,230 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! (656 reviews)
studio room is clean, a soap holder in the shower would be nice

Reviewed on Feb 2, 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! (331 reviews)
Hospitality from the staff… easy check in close to everything… very quiet which I loved…

Reviewed on Jan 2, 2026

Temple Place Suites
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

3 out of 5
28 Fenway Boston MA
Stay at this apartment in Boston. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Fenway Park and Copley Square are located ...
8.6/10 Excellent! (337 reviews)
Amazing

Reviewed on Jan 1, 2026

Maverick Suites at 28 Fenway
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
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
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
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
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

$79
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
Museum of Ice Cream Boston

Museum of Ice Cream Boston Admission Ticket

$44
per adult
Museum of Ice Cream Boston Admission Ticket
Real Pirates Salem Museum General Admission Ticket

Real Pirates Salem Museum General Admission Ticket

$22
per adult
84% of travellers recommend
Real Pirates Salem Museum General Admission Ticket
Built-in 15-minute break at Quincy Market.

The Full Revolutionary Story Epic Small Group Boston Walking Tour

$55
per adult
100% of travellers recommend
The Full Revolutionary Story Epic Small Group Boston Walking Tour
See all activities in Winchester

Cities near Winchester

The statue had me wondering what went through the minds of the brave men and women who have fought for our freedom!

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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