Winchester Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Ana Lei

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winchester Vacation Packages

Winchester Hotel Deals

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
70 Causeway Street Boston MA
Fully refundableReserve now, pay when you stay
The price is ₩203,357 per night from Dec 14 to Dec 15
₩203,357
₩236,816 total
Dec 14 - Dec 15
includes taxes & fees
9.2/10 Wonderful! (4,034 reviews)
I had an absolutely wonderful experience during my stay. From the moment I arrived, the staff made me feel welcomed and taken care of. Check-in was quick and easy, and every team member I encountered was friendly, professional, and genuinely eager to help. The room was spotless, beautifully designed, ...

Reviewed on Nov 14, 2025

citizenM Boston North Station
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 ₩231,471 per night from Nov 30 to Dec 1
₩231,471
₩328,809 total
Nov 30 - Dec 1
includes taxes & fees
9/10 Wonderful! (4,198 reviews)
Spacious room that was spotless. Friendly and helpful staff. My favorite place to stay in Boston!

Reviewed on Nov 14, 2025

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 ₩146,446 per night from Nov 23 to Nov 24
₩146,446
₩170,542 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (2,234 reviews)
The bathrooms were always well attended to and my room was spotless when I showed! Front desk was also very kind and responsive

Reviewed on Nov 11, 2025

The Revolution Hotel
See all 3,924 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 a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(2,499 reviews)

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

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(1,966 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
TD Garden

TD Garden

4.5/5(1,780 reviews)

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.