Winter Hill Vacations

Book a Hotel + Flight or Car together to unlock savings

  • 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

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

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 ₩217,891 per night from Dec 4 to Dec 5
₩217,891
₩261,073 total
Dec 4 - Dec 5
includes taxes & fees
9.6/10 Exceptional! (3,738 reviews)
The food is very good. I have simple tastes and appreciated that the food was not over-processed but was simple yet extremely flavorful.

Reviewed on Nov 25, 2025

Seaport Hotel Boston
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 ₩164,382 per night from Dec 15 to Dec 16
₩164,382
₩191,422 total
Dec 15 - Dec 16
includes taxes & fees
9.2/10 Wonderful! (4,107 reviews)
Rooms were clean, staff was friendly

Reviewed on Nov 25, 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 ₩204,304 per night from Dec 18 to Dec 19
₩204,304
₩297,735 total
Dec 18 - Dec 19
includes taxes & fees
9/10 Wonderful! (4,246 reviews)
Room ready when we arrived at 8:30am Small but suffices Noise from outside is easily heard

Reviewed on Nov 25, 2025

Omni Boston Hotel at the Seaport
See all 3,924 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 . 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
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.