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
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is NZ$367 per night from 5 Feb to 6 Feb
NZ$367
5 Feb - 6 Feb
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! (3,949 reviews)
Amazing gym! Clean rooms and great amenities. Beds were comfortable. We were snowed in and the hotel restaurants stayed open when everything in Boston was shut down.

Reviewed on 27 Jan 2026

Seaport Hotel Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is NZ$207 per night from 8 Feb to 9 Feb
NZ$207
8 Feb - 9 Feb
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! (6,194 reviews)
All around clean and cozy…also great location

Reviewed on 31 Jan 2026

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,433 reviews)
Really good place. Walking distance anywhere

Reviewed on 31 Jan 2026

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The Revolution Hotel
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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.
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! (655 reviews)
Staff was friendly and helpful. Apartment was spotless. It was so cute, modern, and intimate. I love that it was completely furnished and included everything you need for a functional kitchen including cookware, dinnerware, utensils, numerous appliances, etc. Exceeded all my expectations, will definitely ...

Reviewed on 28 Jan 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 Wi-Fi, 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 2 Jan 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 Wi-Fi, laundry facilities and concierge services. Popular attractions Fenway Park and Copley Square are located ...
8.6/10 Excellent! (335 reviews)
Amazing

Reviewed on 1 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

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 Foxboro. 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

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
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
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$92
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

NZ$59
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$137
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$146
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

NZ$40
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Built-in 15-minute break at Quincy Market.

The Full Revolutionary Story Epic Small Group Boston Walking Tour

NZ$96
per adult
100% of travellers recommend
The Full Revolutionary Story Epic Small Group Boston Walking Tour
See all activities in Winchester

Cities near Winchester

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

Boston