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
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
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! (6,293 reviews)
The room was okay. We had a window but it just was a view of a wall. The hotel location was amazing, we walked all over.

Reviewed on 21 Feb 2026

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Harborside Inn Of Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
The price is ฿3,902 per night from 22 Feb to 23 Feb
฿3,902
฿5,815 total
22 Feb - 23 Feb
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! (4,498 reviews)
Was a pleasant night

Reviewed on 20 Feb 2026

Omni Boston Hotel at the Seaport
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! (2,486 reviews)
Staffs were very friendly. I w

Reviewed on 20 Feb 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! (662 reviews)
Great staff, clean, and location

Reviewed on 18 Feb 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! (332 reviews)
Very spacious

Reviewed on 15 Feb 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! (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 a sporting event and night scenes 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 a skyscraper, landscape views and a park

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
Harvard University showing a city and heritage architecture

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

Things to do

Boston Hop-On Hop-Off Trolley Tour

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

฿1,670
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

฿1,082
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

฿891
per adult
100% of travellers recommend
LEGO Discovery Center Boston Admission Ticket
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

฿732
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
The artist curates a studio wall.

The Art of Paul Pedulla

฿849
per adult
The Art of Paul Pedulla
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

฿2,674
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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Cities near Winchester

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

Boston