Winter Hill Vacations from ￥279,969
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The Latest Winter Hill Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston
Back Bay
per person
Aug 23 - Aug 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
We booked through Expedia. They charge rooms that booked through discount sites an “urban fee of $35 per night for your convenience”. Whether you want something or not, you are charged an additional $35 and this is only for rooms that book with a discount rate. We were given a room with no working refrigerator- they brought a banged up one up and it was placed in the room randomly. We were not able to access a movie which was part of their “urban deal”. Phone to concierge either wasn’t working or no one was answering around 9:30 pm so had to get redressed and head downstairs to ask a question. It’s a beautiful hotel and the people behind the scenes were so kind but we were definitely treated like reduced rate guests.
Reviewed on Jul 14, 2025
Boston Harbor Hotel
North End
Save 100% on your flight
per person
Aug 23 - Aug 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Location is perfect. A lots of places to see within walking distance and good restaurants nearby too. The service is great. Friendly and professional staff. The room is clear and spacious. The gym is very big with all the equipments and have personal training rooms too. We stayed 5 nights and were very lucky to get room on 16th floor with a balcony!
Reviewed on Jul 14, 2025
Raffles Boston
Back Bay
Save 100% on your flight
per person
Aug 23 - Aug 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.
Reviewed on Jul 14, 2025
The Charles Hotel
West Cambridge
per person
Aug 23 - Aug 30
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,007 reviews)
We had high hopes for this hotel after visiting its restaurant last year and seeing the lobby and reviews. Unfortunately, we were first booked on the 9th floor during a heat wave. The musty smell of the room was so strong when we opened the door. The hotel did right by us and moved us to a lower floor. The person from the front desk that moved our room was lovely - so friendly and understanding. The new room was wonderful and the TV had a better picture as well. We later learned that the musty smell can occur on the higher floors when the temperature is high. Why put us there to begin with then?
In addition, there is no refrigerator in the room unless you request one. Maybe not a big deal for some, but we like to keep our water cold.
I am glad that the hotel ended up doing right by us, but still question the decision to put us on the 9th floor at the start.
Reviewed on Jul 12, 2025
Where to stay in Winter Hill
Find the best Winter Hill areas and neighborhoods for the activities you enjoy most. Learn more about Winter Hill
Downtown Boston
4.5/5(2,415 area reviews)
Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.
Winter Hill Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥31,448 per night from Aug 10 to Aug 11
￥31,448
￥42,691 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,695 reviews)
"Room was spacious and clean. The restaurants in the hotel were great, a little costly but delicious food."
Reviewed on Jul 16, 2025
citizenM Boston Back Bay
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥27,208 per night from Jul 20 to Jul 21
￥27,208
￥31,684 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,445 reviews)
"loved staying here. there is plenty of space to relax and make time pass by while you explore boston. the rooms were clean and chic. would recommend to a friend :)"
Reviewed on Jul 16, 2025
Harborside Inn Of Boston
185 State St, Boston, MA
The price is ￥30,476 per night from Jul 27 to Jul 28
￥30,476
￥35,489 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (5,319 reviews)
"Good stay"
Reviewed on Jul 15, 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.
Frequently asked questions
Discover the most popular places to visit in Winter Hill
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.
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.
Boston Common
4.5/5(4,786 reviews)
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.
Things to do
Boston CityPASS®: Admission to Top 4 Attractions
￥11,581
per adult
90% of travellers recommend
View Boston Observation Deck Admission Tickets
￥4,984
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.