Winchester Holidays

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Top hotels in Winchester

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is S$161 per night from 21 Dec to 22 Dec
S$161
21 Dec - 22 Dec
includes taxes & fees
9.2/10 Wonderful! (6,027 reviews)
Room was clean and spacious! The staff was very welcoming every time we came back! Would definitely stay there again!! Was within walking distance to a lot of sights!

Reviewed on 10 Dec, 2025

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
Fully refundableReserve now, pay when you stay
The price is S$325 per night from 1 Jan to 2 Jan
S$325
1 Jan - 2 Jan, 2026
includes taxes & fees
9/10 Wonderful! (4,285 reviews)
Room was neat but too small. We did not liked that we ordered room service thinking they will bring the cart with the food in regular dishes and utensils, like in any hotel of this level, and instead they brought our food in a shopping bag on disposable containers/plastic utensils(???). There was ...

Reviewed on 10 Dec, 2025

Omni Boston Hotel at the Seaport
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is S$251 per night from 21 Dec to 22 Dec
S$251
21 Dec - 22 Dec
includes taxes & fees
8.4/10 Very Good! (1,241 reviews)
Staff was fantastic

Reviewed on 8 Dec, 2025

Hilton Boston Back Bay
See all 3,978 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 a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University featuring a city and heritage architecture

Harvard University

4.5/5(102 reviews)

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

New England Aquarium

4.5/5(57 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

What to do in Winchester

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$103
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 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

S$44
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Go City: Boston All-Inclusive Pass with 45+ Attractions

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

S$110
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Winchester

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