Winter Hill Holidays

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to HK$890 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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)

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Harbor and Boston Massacre Site, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotel + flight trips in Downtown Boston

Top hotels in Winter Hill

Omni Parker House
Omni Parker House
4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is HK$1,735 per night from 16 Jun to 17 Jun
HK$1,735
per night
16 Jun - 17 Jun
8.8/10 Excellent! (2,659 reviews)
Timeless Royalty
"My friend and I grew up in Boston knowing the history and lore of the Omni Parker House. Since neither of us live there anymore, and we were planning a trip home, we knew we had to stay here. The luxury of yesteryear is top tier. We truly felt like royalty."

Reviewed on 23 May 2024

Omni Parker House
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
The price is HK$1,927 per night from 9 Jun to 10 Jun
HK$1,927
per night
9 Jun - 10 Jun
9/10 Wonderful! (2,078 reviews)
"Aside from it being big and easy to get turned around, it is a very nice and convenient property"

Reviewed on 25 May 2024

Omni Boston Hotel at the Seaport
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is HK$2,102 per night from 16 Jun to 17 Jun
HK$2,102
per night
16 Jun - 17 Jun
9.6/10 Exceptional! (2,166 reviews)
"Every staff member was fantastic and eager to make your stay wonderful"

Reviewed on 25 May 2024

Seaport Hotel Boston
See all 3,231 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 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 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.

Popular places to visit

Image for Fenway Park

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
Image for Harvard University

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
Image for New England Aquarium

New England Aquarium

4.5/5(57 reviews)

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium

Things to do

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

HK$617
Per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Image for Bewitched Walking Tour of Salem

Bewitched Walking Tour of Salem

HK$234
Per adult
100% of travellers recommend
Bewitched Walking Tour of Salem
Image for Odyssey Boston Premier Elegant Dinner Cruise

Odyssey Boston Premier Elegant Dinner Cruise

HK$1,695
Per adult
Odyssey Boston Premier Elegant Dinner Cruise
See all activities in Boston

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.