Winter Hill Vacations from ￥165,818

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

The Latest Winter Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥204,114, price is now ￥165,818 per person
￥165,818
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
17.2/10 Exceptional! (1,337 reviews)
Staff were very courteous! Clean room!

Reviewed on Nov 15, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥308,703, price is now ￥207,566 per person
￥207,566
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
19.6/10 Exceptional! (1,005 reviews)
Beautiful room with a view. The fitness center and spa was great!

Reviewed on Nov 17, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥303,367, price is now ￥217,692 per person
￥217,692
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
19.2/10 Exceptional! (482 reviews)
The room was wonderful, the bed was heaven. Room service was delicious and the overall aesthetic and ambience of the lobby and common areas were fabulous

Reviewed on Nov 18, 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was ￥254,466, price is now ￥187,147 per person
￥187,147
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
18.4/10 Exceptional! (2,268 reviews)
Room was really clean!!

Reviewed on Nov 17, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥291,086, price is now ￥233,224 per person
￥233,224
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
18.8/10 Exceptional! (536 reviews)
This hotel has it all, best in class care and service.

Reviewed on Oct 24, 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 which includes night scenes and a city as well as a small group of people

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.

Find hotels in Downtown Boston

Winter Hill 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 ￥19,002 per night from Nov 30 to Dec 1
￥19,002
￥22,128 total
Nov 30 - Dec 1
includes taxes & fees
9.2/10 Wonderful! (4,060 reviews)
Room was cute and compact. The view from the causeway was amazing. Centrally located to all things i wanted to walk to and the train station.

Reviewed on Nov 20, 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 ￥28,618 per night from Dec 21 to Dec 22
￥28,618
￥39,664 total
Dec 21 - Dec 22
includes taxes & fees
9/10 Wonderful! (4,225 reviews)
Room was extremely clean, wonderful smell. We received extra amenities in honor of our anniversary. They have everything you need from restaurants, pools, and activities.

Reviewed on Nov 18, 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 ￥13,081 per night from Nov 24 to Nov 25
￥13,081
￥15,232 total
Nov 24 - Nov 25
includes taxes & fees
9/10 Wonderful! (2,257 reviews)
Great hotel! no bathroom in the room

Reviewed on Nov 18, 2025

The Revolution Hotel
See all 3,879 properties in Winter Hill
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

How much does a Winter Hill vacation package cost?
We make it simple to see the world, with Winter Hill packages starting from just ￥165,818. You'll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a few tours and activities to your travel itinerary?
How do I get a cheap travel package to Winter Hill?
Book everything in the one place with our Winter Hill vacation packages. We have deals on flights, hotels and more that'll keep your pocket happy and your adventurous spirit alive. And, with more than 550 air carriers and 1,000,000 hotel options throughout the world to pick from, there are endless opportunities to mix and match.
Where should I stay in Winter Hill?
A trip to Winter Hill isn't complete without stopping by Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Spend your nights near these popular attractions and make sightseeing simple.
What are the top hotels in Winter Hill?
When it comes to comfy places to stay in Winter Hill, you can't go past Top Floor Of One Family Home. Have a look at our deals and land a bargain.
How far in advance should I book my Winter Hill vacation?
Travelers are usually able to look up international airfares on Expedia within 12 months of the departure date. Booking last minute? With a little bit of luck, it's still possible to nab a cheap ticket only weeks before your flight.
What does an Expedia Winter Hill travel package include?
From airfares and hotels to rental cars, Expedia can help you craft a Winter Hill package that's ideal for you. Vacationing for a week or longer? Consider a rental car, flight and hotel bundle. If you're taking a short break, a hotel and airfare deal may be more your style. Experiences can also be added once you've made your booking. Our vacation packages make it a breeze to save and plan.
What should I know before booking a Winter Hill travel package?
You'll save plenty with an Expedia travel package. Bundle your airfares, rental cars and hotels and pick up great discounts. Hotels aren't your only option, however. Book with us and select from beachside condos, rural cottages and even ranches and treehouses!
Can I choose my airline with a Winter Hill Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Winter Hill vacation package?
It's good to know that you can cancel your Winter Hill booking if your plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Winter Hill

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
Boston Common featuring landscape views, a skyscraper and flowers

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.

Boston Common
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

Things to do

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

￥5,190
per adult
86% of travellers recommend
View Boston Observation Deck Admission Tickets
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥12,060
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥8,312
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.