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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Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is £140 per night from 8 Mar to 9 Mar
£140
8 Mar - 9 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! (4,044 reviews)
Very helpful and kind staff. Clean rooms and comfy beds. Will stay again!

Reviewed on 25 Feb 2026

Seaport Hotel 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 £117 per night from 1 Mar to 2 Mar
£117
1 Mar - 2 Mar
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! (4,503 reviews)
Good people and nice service

Reviewed on 26 Feb 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 £135 per night from 8 Mar to 9 Mar
£135
8 Mar - 9 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! (3,101 reviews)
Very attentive and friendly staff , clean rooms . Our stay was very pleasant

Reviewed on 25 Feb 2026

Hilton Boston Park Plaza
See all 4,176 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
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! (665 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
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

£38
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

£58
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

£17
per adult
92% of travellers recommend
Harvard University Campus Guided Walking 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

£25
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

£26
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

£61
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Winchester

Cities near Winchester

Cold but sunny A day out stretching my lazy legs..... 🚶🏻‍♀️🚶🏻‍♀️🚶🏻‍♀️🚶🏻‍♀️

Medford

Woburn showing an administrative building and street scenes

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

Skyline of Boston

Stoneham

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