Winter Hill Holidays

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Your Winter Hill Holiday

Take the fuss out of organising your next escape by booking a Winter Hill holiday package. Immerse yourself in the sounds and sights of this wonderful neighbourhood and experience what it has to offer. When it's time to take in the sights, you'll find lots of popular attractions nearby including Assembly Row, LEGOLAND® Discovery Centre and Somerville Theatre. Visit one, two or all during your trip to Winter Hill. No matter your travel plans or budget, booking your dream Winter Hill holiday is simple with Expedia.

Our guide on 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 showing a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(17 area reviews)

This is Boston’s business district, now and back when the city was just starting.

Find hotels in Downtown Boston

Our pick of the best 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 AU$296 per night from 28 Nov to 29 Nov
AU$296
28 Nov - 29 Nov
includes taxes & fees
9.6/10 Exceptional! (3,658 reviews)
Yes

Reviewed on 2 Nov 2025

Seaport Hotel Boston
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 AU$187 per night from 23 Nov to 24 Nov
AU$187
23 Nov - 24 Nov
includes taxes & fees
9/10 Wonderful! (2,209 reviews)
Really nice room

Reviewed on 5 Nov 2025

The Revolution Hotel
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 AU$240 per night from 30 Nov to 1 Dec
AU$240
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (3,985 reviews)
Perfect room, loved that you can decide when you need cleaning/housekeeping, room had everything we needed and was super comfy and I loved how everything was controlled by phone or the Ipad, would recommend to everyone! This hotel was in a great location too and you couldn't hear any noise from outside ...

Reviewed on 3 Nov 2025

citizenM Boston North Station
See all 3,878 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Discover the most popular places to visit in Winter Hill

Fenway Park which includes night scenes and a sporting event 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
TD Garden

TD Garden

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
Harvard University which includes heritage architecture and a city

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

Activities

Whale-Watching Cruise in Stellwagen Bank Marine Sanctuary

City Cruises: Boston Harbor New England Aquarium Whale-Watching Cruise

AU$130
per adult
86% of travellers recommend
City Cruises: Boston Harbor New England Aquarium Whale-Watching Cruise
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

AU$83
per adult
86% of travellers recommend
Boston Harbor Sunset Cruise
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

AU$128
per adult
76% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
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.