Winchester Holidays

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Winchester Holiday

Our pick of the best Winchester Hotel Deals

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 NZ$399 per night from 5 Apr to 6 Apr
NZ$399
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (4,526 reviews)
Everything was well clean the stay was awesome.

Reviewed on 19 Mar 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
The price is NZ$357 per night from 22 Mar to 23 Mar
NZ$357
22 Mar - 23 Mar
includes taxes & fees
8.4/10 Very Good! (3,116 reviews)
Good hotel

Reviewed on 18 Mar 2026

Hilton Boston Park Plaza
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 NZ$287 per night from 5 Apr to 6 Apr
NZ$287
5 Apr - 6 Apr
includes taxes & fees
9.6/10 Exceptional! (4,070 reviews)
Easy check-in and check-out! Room was clean and spacious. The bed was soft as were the pillows.

Reviewed on 19 Mar 2026

Seaport Hotel Boston
See all 4,173 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.

Discover the most popular places to visit in Winchester

Fenway Park which includes night scenes and a sporting event as well as a large group of people

Fenway Park

4.5/5(9 reviews)

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

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
Harvard University which includes heritage architecture and a city

Harvard University

4.5/5(27 reviews)

You don’t have to be a history student to appreciate the unique heritage of this world-renowned academic institution.

Harvard University

What to do in Winchester

Boston Hop-On Hop-Off Trolley Tour

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

NZ$87
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

NZ$60
per adult
98% of travellers recommend
History and Hauntings of Salem Guided Walking Tour
Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

NZ$38
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Winchester

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