Winchester Travel Guide

Tourist 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

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Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
The price is AU$273 per night from 22 Mar to 23 Mar
AU$273
22 Mar - 23 Mar
includes taxes & fees
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 rooms in ...
8.4/10 Very Good! (3,130 reviews)
EVERYTHING WAS PERFECT !!, LOCACATION, HOTEL AND THE STAFF

Reviewed on 9 Mar 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is AU$252 per night from 10 Mar to 11 Mar
AU$252
10 Mar - 11 Mar
includes taxes & fees
Stay at this hotel in Boston. Enjoy free Wi-Fi, a 24-hour front desk and a business centre. Our guests praise the breakfast and the restaurant in their reviews. ...
9.2/10 Wonderful! (6,374 reviews)
Nice

Reviewed on 9 Mar 2026

Harborside Inn Of Boston
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is AU$315 per night from 22 Mar to 23 Mar
AU$315
22 Mar - 23 Mar
includes taxes & fees
Stay at this business-friendly hotel in Boston. Enjoy free Wi-Fi, 2 restaurants and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (4,052 reviews)
Room was clean but the hair conditioner dispenser was empty. I didn’t bring my own expecting a supply at the hotel so it did create an issue for me. Staff was extremely nice. Minor detail but inconvenient that the light at the coffee bar didn’t work.

Reviewed on 9 Mar 2026

Seaport Hotel Boston
See all 4,194 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 Wi-Fi, laundry facilities and cable TV channels. Popular attractions Boston Common and New England Aquarium are ...
7.2/10 Good! (334 reviews)
Shower was an issue but got it resolved

Reviewed on 26 Feb 2026

Temple Place Suites
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
8 Harrison Ave Boston MA
Stay at this business-friendly aparthotel in Boston. Enjoy free Wi-Fi, a 24-hour front desk and a 24-hour business centre. Our guests praise the helpful staff ...
8/10 Very Good! (666 reviews)
Location is great. Quiet rooms. Easy to get in and out of the building. Easy check in and check out

Reviewed on 25 Feb 2026

Global Luxury Suites Downtown Boston
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 Wi-Fi, laundry facilities and concierge services. Popular attractions Fenway Park and Copley Square are located ...
8.6/10 Excellent! (337 reviews)
I stayed here for an extended stay after relocation from my apartment. I had been staying in the same unit and it was not expressed as to for my second extension I was to be relocated. I received a call in the middle of the work day saying I needed to move all my stuff. I was met with a rude temperament ...

Reviewed on 31 Jan 2026

Maverick Suites at 28 Fenway
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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 which includes night scenes and a sporting event as well as a large group of people

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 theatre scene and great live music.

Gillette Stadium
Boston Common which includes landscape views, a skyscraper and a park

Boston Common

The oldest public park in the United States, Boston Common is the ideal place to relax, unwind and soak up some history.

Boston Common
Harvard University which includes heritage architecture and a city

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'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
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

Activities

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

AU$74
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

AU$51
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

AU$33
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$119
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

AU$69
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

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

AU$76
per adult
98% of travellers recommend
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions
See all activities in Winchester

Cities near Winchester

Quincy Market showing a city, an administrative buidling and heritage architecture

Boston