Winthrop Vacations from ￥52,750
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Better together
Save up to ￥45,448 when you book a flight and hotel together*
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With over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Winthrop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Porter Square Hotel
North Cambridge
Price was ￥77,304, price is now ￥52,750 per person
￥52,750
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.2/10 Wonderful! (1,008 reviews)
Great location to transportation, dining and shopping. Friendly staff. Clean and safe.
Definitely recommend for a stay in Boston
Reviewed on Sep 28, 2025
Boston Harbor Hotel
North End
Save 100% on your flight
Price was ￥606,232, price is now ￥332,338 per person
￥332,338
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
The Boston Harbor Hotel is absolutely gorgeous! The staff are extremely polite, professional and always happy to help!
Our room was beautiful and the views of the harbor were great! Loved the location being walkable to so many great spots! Would absolutely stay here again!
Reviewed on Sep 29, 2025
The Whitney Hotel
Beacon Hill
Save 100% on your flight
Price was ￥173,358, price is now ￥112,988 per person
￥112,988
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (457 reviews)
We love the Whitney and it is our first choice when in Boston and we refer many to stay with you. The property is lovely, the location fantastic and staff excellent.
Reviewed on Sep 30, 2025
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was ￥167,994, price is now ￥112,736 per person
￥112,736
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (1,002 reviews)
This is the first time we have stayed at this property. The location, accommodations and staff were fantastic. I was especially impressed by the customer service provided by the staff. Every staff member greeted us personally, asked if we needed anything and invariably wished us a good day. The staff alone made our stay a pleasure-able experience.
Reviewed on Sep 17, 2025
Hyatt Place Boston/Medford
Save 100% on your flight
Price was ￥86,866, price is now ￥58,462 per person
￥58,462
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.4/10 Very Good! (1,449 reviews)
Nice hotel but needs updating inside rooms!
Reviewed on Sep 27, 2025
Find the Best Winthrop Vacation Packages
Winthrop Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥35,382 per night from Oct 30 to Oct 31
￥35,382
￥47,231 total
Oct 30 - Oct 31
includes taxes & fees
9/10 Wonderful! (4,082 reviews)
"For our trip to Boston, this location worked out well! The hotel was comfortable, well appointed and had ample onsite parking. We were able to park the car and leave it for the 4 days-walked or took “the T” everywhere. Lots of restaurants nearby but the hotel also had really good options too!"
Reviewed on Sep 28, 2025
citizenM Boston North Station
70 Causeway Street, Boston, MA
The price is ￥34,029 per night from Oct 5 to Oct 6
￥34,029
￥39,628 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (3,855 reviews)
"Great location! Very nice hotel, comfortable and clean"
Reviewed on Sep 27, 2025
The Dagny Boston
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥29,215 per night from Oct 31 to Nov 1
￥29,215
￥39,189 total
Oct 31 - Nov 1
includes taxes & fees
9.4/10 Exceptional! (6,553 reviews)
"Very nice"
Reviewed on Sep 27, 2025
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 Winthrop
Fenway Park
Catch a game or take a tour at one of America’s most historic and beloved ballparks.
Harvard University
Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.
Boston Common
The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.
What to do in Winthrop
Boston CityPASS®: Admission to Top 4 Attractions
￥11,572
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
￥4,980
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
