Winchester Holidays

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Top hotels in Winchester

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is S$385 per night from 25 May to 26 May
S$385
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (4,304 reviews)
The breakfast very good

Reviewed on 9 May, 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
Fully refundableReserve now, pay when you stay
The price is S$357 per night from 25 May to 26 May
S$357
25 May - 26 May
includes taxes & fees
9.2/10 Wonderful! (4,646 reviews)
We were at an event that was for over 900 people, the food came out hot and delicious. The wait staff were extremely friendly and helpful. The entire event was flawless.

Reviewed on 9 May, 2026

Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is S$187 per night from 25 May to 26 May
S$187
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (2,608 reviews)
Very Lovely Place, Nice Architecture.

Reviewed on 10 May, 2026

The Revolution Hotel
See all 4,205 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

Fenway Park

4.5/5(62 reviews)

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

Fenway Park
Harvard University

Harvard University

4.5/5(104 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 Hop-On Hop-Off Trolley Tour

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

S$67
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
History and Hauntings of Salem Guided Walking Tour

History and Hauntings of Salem Guided Walking Tour

S$39
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$107
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities in Winchester

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