Winter Hill Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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(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 S$357 per night from 24 Aug to 25 Aug
S$357
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,826 reviews)
"Lovely upscale hotel. Staff are friendly, knowledgeable and helpful. This hotel is in an Ideal location, within walking distance walking distance of tourist attractions. Roof top pool is clean and enjoyable. The beds are comfortable, the bathroom and shower are clean and relaxing. I recommend staying ..."

Reviewed on 11 Aug, 2025

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is S$292 per night from 1 Sept to 2 Sept
S$292
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (3,198 reviews)
"Very convenient. Very efficient."

Reviewed on 10 Aug, 2025

Hilton Boston Park Plaza
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 S$282 per night from 24 Aug to 25 Aug
S$282
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (1,589 reviews)
"A really great hotel in a wonderful location. With super-comfy beds, lovely linen and all mod cons, the room is small but perfectly formed. I was surprised that despite the busy road outside, it really is quiet and tranquil inside. Everything works, too - seems like an obvious point but not always ..."

Reviewed on 10 Aug, 2025

citizenM Boston Back Bay
See all 3,723 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 showing a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University featuring a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
New England Aquarium

New England Aquarium

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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$101
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

S$90
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
BEST New York City Day Tour from Boston

New York City Day Tour from Boston

S$225
per traveller
100% of travellers recommend
New York City Day Tour from Boston
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.