Winchester Holidays

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Winchester Holiday

Our pick of the best Winchester Hotel Deals

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$367 per night from 5 Feb to 6 Feb
NZ$367
5 Feb - 6 Feb
includes taxes & fees
9.6/10 Exceptional! (3,949 reviews)
Amazing gym! Clean rooms and great amenities. Beds were comfortable. We were snowed in and the hotel restaurants stayed open when everything in Boston was shut down.

Reviewed on 27 Jan 2026

Seaport Hotel Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
The price is NZ$207 per night from 8 Feb to 9 Feb
NZ$207
8 Feb - 9 Feb
includes taxes & fees
9.2/10 Wonderful! (6,194 reviews)
All around clean and cozy…also great location

Reviewed on 31 Jan 2026

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (2,433 reviews)
Really good place. Walking distance anywhere

Reviewed on 31 Jan 2026

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The Revolution Hotel
See all 4,218 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

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 Foxboro. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium
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

What to do in Winchester

Boston Hop-On Hop-Off Trolley Tour

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

NZ$92
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
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

NZ$59
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$137
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
See all activities in Winchester

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