Winchester

Travel 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 €187 per night from 5 Feb to 6 Feb
€187
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! (3,937 reviews)
Wonderful staff and great experience!

Reviewed on 28 Jan 2026

Seaport Hotel Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Fully refundable
The price is €114 per night from 3 Feb to 4 Feb
€114
3 Feb - 4 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! (6,189 reviews)
Clean, comfortable bed

Reviewed on 26 Jan 2026

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
The price is €77 per night from 2 Feb to 3 Feb
€77
2 Feb - 3 Feb
includes taxes & fees
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! (2,423 reviews)
The front desk lady was friendly and helpful. The room and bathrooms were extremely clean. The hotel had a great vibe. At the price, it exceeded my expectations.

Reviewed on 27 Jan 2026

The Revolution Hotel
See all 4,212 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! (653 reviews)
The staff was so kind and helpful and so sweet!!! I’ve never had a better experience with the staff being so friendly I love them, thank you for the best experience.

Reviewed on 23 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
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 showing 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 Foxboro. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium
Boston Common showing a garden, a city and a skyscraper

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
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
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
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 CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€67
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

€72
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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

€29
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

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

€46
per adult
98% of travellers recommend
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions
The artist curates a studio wall.

The Art of Paul Pedulla

€23
per adult
The Art of Paul Pedulla
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

€24
per adult
100% of travellers recommend
LEGO Discovery Center Boston Admission Ticket
See all activities in Winchester
Quincy Market showing a city, an administrative buidling and heritage architecture

Boston