Winchester Travel Guide

Tourist 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
The price is NZ$399 per night from 5 Apr to 6 Apr
NZ$399
5 Apr - 6 Apr
includes taxes & fees
Stay at this luxury hotel in Boston. Enjoy free Wi-Fi, a full-service spa and 4 restaurants. Our guests praise the breakfast and the pool in their reviews. Popular ...
9.2/10 Wonderful! (4,526 reviews)
Everything was well clean the stay was awesome.

Reviewed on 19 Mar 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
The price is NZ$357 per night from 22 Mar to 23 Mar
NZ$357
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! (3,116 reviews)
Good hotel

Reviewed on 18 Mar 2026

Hilton Boston Park Plaza
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is NZ$287 per night from 5 Apr to 6 Apr
NZ$287
5 Apr - 6 Apr
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! (4,070 reviews)
Easy check-in and check-out! Room was clean and spacious. The bed was soft as were the pillows.

Reviewed on 19 Mar 2026

Seaport Hotel Boston
See all 4,173 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! (336 reviews)
Love the location

Reviewed on 18 Mar 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! (669 reviews)
My only complaint with this property is the description for parking. It was definitely misleading. Parking is not on property and staff was not able to answer specific questions due to parking being through another vendor.! I feel like this needs to be more specific in the description.

Reviewed on 17 Mar 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 Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff in their 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 10 Mar 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

Fenway Park which includes night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(9 reviews)

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

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
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(27 reviews)

You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.

Harvard University
Boston Common which includes landscape views, a skyscraper and a park

Boston Common

4.5/5(32 reviews)

Trace the history of Boston and take a break from the city heat in the USA’s oldest public park.

Boston Common
Boston's Zakim Bridge

TD Garden

4.5/5(6 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
New England Aquarium featuring marine life

New England Aquarium

4/5(7 reviews)

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

NZ$87
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

NZ$60
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

NZ$38
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

NZ$57
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$132
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

NZ$140
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Winchester

Cities near Winchester

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

Boston