Winter Hill Holidays

Book a Hotel + Flight or Car together to unlock savings

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 Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

Find hotels in Downtown Boston

Top hotels in Winter Hill

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
9.2/10 Wonderful! (6,176 reviews)
Nice staff, great location

Reviewed on 20 Jan 2026

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Harborside Inn Of Boston
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Fully refundableReserve now, pay when you stay
The price is 9.273.663 ₫ per night from 22 Feb to 23 Feb
9.273.663 ₫
10.799.180 ₫ total
22 Feb - 23 Feb
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
Room was extremely clean, staff was beyond wonderful and helpful. Our new favorite hotel!

Reviewed on 19 Jan 2026

The Langham, 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 2.059.551 ₫ per night from 26 Jan to 27 Jan
2.059.551 ₫
2.398.348 ₫ total
26 Jan - 27 Jan
includes taxes & fees
9/10 Wonderful! (2,401 reviews)
This was good for a quick stay. The single room was small, but comfortable and had everything you’d need in a hotel. The only problem I had was with parking. Although it is mentioned that there is no parking lot, I was not aware that my only feasible option was staying in a parking garage for an ...

Reviewed on 20 Jan 2026

The Revolution Hotel
See all 3,945 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 1null000null000 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 an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Gillette Stadium is also home to the New England Revolution, our pro soccer team. Tickets are easy to get and not crazy expensive. And there is always a section reserved for the hooligans, who keep the energy up for the whole stadium!

Gillette Stadium

3/5(2 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's acclaimed theatre scene and great live music.

Gillette Stadium
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Harvard University