Winchester, MA

Travel Guide

A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.
An aerial view of a town with a lake, church steeples, and a bridge.
A historic building with a clock tower, red brick walls, and a green roof.
A city skyline with industrial buildings and a highway.
A rocky hillside with scattered boulders and dense green foliage.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundable
$394 nightly
The price is $459 total per night from Oct 2 to Oct 3
$459 total
Oct 2 - Oct 3
Total with taxes and fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$265 nightly
The price is $308 total per night from Sep 27 to Sep 28
$308 total
Sep 27 - Sep 28
Total with taxes and fees
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,939 reviews)
"Only problem was that Bar was never open during my stay"

Reviewed on Sep 22, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$304 nightly
The price is $353 total per night from Oct 4 to Oct 5
$353 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
Seaport Hotel Boston
See all 4,032 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.
Premier Suites - Bay Village

Premier Suites - Bay Village

2 out of 5
1-3-5 Cortes Street Boston MA
Stay at this aparthotel in Boston. Enjoy free WiFi and laundry facilities. Popular attractions Copley Square and Boston Common are located nearby.
6.4/10 (345 reviews)
"We should have read more reviews before booking. I am 75 years old, traveled extensivly throughout my career and have never, ever had such a poor, scary experience. From the moment we walked into the building we were appalled at the condition. There was a hole in the wall of our room, where the AC ..."

Reviewed on Sep 18, 2026

Premier Suites - Bay Village
Temple Place Suites

Temple Place Suites

2.5 out of 5
29 Temple Place Boston MA
Stay at this apartment in Boston. Enjoy free WiFi, laundry facilities, and cable TV channels. Popular attractions Boston Common and Faneuil Hall Marketplace ...
7.2/10 Good! (478 reviews)
"Everything was clean and as expected. Great value. Would stay again."

Reviewed on Sep 21, 2026

Temple Place Suites
Crescent Suites Hotel

Crescent Suites Hotel

3 out of 5
287 Crescent Street Waltham MA
Book a stay at this business-friendly aparthotel in Waltham. Enjoy a fitness center, a business center, and a garden. Our guests praise the helpful staff and ...
Crescent Suites 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.

Stay near popular Winchester attractions

Winter Pond

9.0/10 (2 reviews)
Enjoy an outing to Winter Pond during your stay in Winchester. Discover the top-notch restaurants and acclaimed art scene in this vibrant area.
See properties

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$37
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$46
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Museum of Ice Cream Boston Admission Ticket

Museum of Ice Cream Boston Admission Ticket

$44
per adult
80% of travellers recommend
Museum of Ice Cream Boston Admission Ticket
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

$28
per adult
LEGO Discovery Center Boston Admission Ticket
See all activities in Winchester

Cities near Winchester

A statue on a rock formation in a snowy park with houses and a tall tower in the background.

Lexington

A vintage truck parked in a field with a wooden house in the background.

Medford

A red brick building with white columns and a green lawn with pink flowers.

Woburn

An aerial view of a city with two large lakes, a highway, and residential areas.

Arlington

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