Winter Hill Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    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 a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Winter Hill

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿6,852 per night from 10 Aug to 11 Aug
฿6,852
฿9,301 total
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (3,663 reviews)
"Amazing Stay! One thing I would suggest is…you know what nvm. I’ll be back anyway. - Roger"

Reviewed on 11 Jul 2025

Omni Boston Hotel at the Seaport
citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,969 per night from 20 Jul to 21 Jul
฿5,969
฿6,951 total
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (1,405 reviews)
"Good location. Cool European concept hotel. Good food and drink options. Would stay again. No onsite parking."

Reviewed on 10 Jul 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
9/10 Wonderful! (5,300 reviews)
"We were pleasantly surprised by how convenient Harborside Inn was to downtown and the waterfront. Access to the transit station is literally right outside, which puts the rest of Boston and the airport just a few steps away. The hotel was clean, quiet, and comfortable. Harborside will be our place ..."

Reviewed on 10 Jul 2025

Get rates
Harborside Inn Of Boston
See all 3,693 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 holiday 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 favourite 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 holiday 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 Centre 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 holiday?
Travellers 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. Holidaying 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 holiday 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 holiday package?
Yes --- and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our holiday 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 holiday 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.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 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(102 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
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

4.5/5(204 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

Things to do

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

฿2,578
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

฿1,712
per adult
88% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

฿1,777
per adult
84% 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.