Winter Hill Vacations

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Your Winter Hill Vacation

Organizing your next break just got easier with a vacation package to Winter Hill. Embrace the best this neighborhood has to offer while making fond memories that'll stay with you for years. When it's time to take in the sights, you'll find lots of top attractions nearby including Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Visit one, two or more during your trip to Winter Hill. No matter what your dream Winter Hill vacation looks like, you can turn it into reality with Expedia.

The Latest Winter Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
7.4/10 Good! (189 reviews)
The grounds are well kept. The staff are very friendly and helpful. The building itself is tired. The kitchenette had no utensils and only paper cups. Also the hot plate didn’t have a place to plug in. The fridge and microwave worked though and that’s all we needed. Just a heads up in case you need more. They had a variety of breakfast options that are included. Pancakes, waffles, eggs, muffins etc. For the price, we were happy.

Reviewed on Jun 3, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Boston (BOS)
9.6/10 Exceptional! (1,001 reviews)
Always a great stay. Property is getting a little bit dated and could use a refresh. The house keeping staff is the best!

Reviewed on Jun 3, 2024

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 17
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (217 reviews)
Beautiful room, amenities, service, snacks and coffee station.

Reviewed on May 26, 2024

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Excellent experience

Reviewed on Jun 3, 2024

The Dagny Boston

The Dagny Boston

4 out of 5
Downtown Boston
Save 100% on your flight
per person
Aug 12 - Aug 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (3,580 reviews)
We've been staying at this property for more than 10 years, when it was still a Hilton. The location is ideal, the rooms are spacious and comfortable, and the service, especially Ed the doorman, is outstanding.

Reviewed on Jun 5, 2024

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(2,415 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Find hotel + flight trips in Downtown Boston

Winter Hill Hotel Deals

Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is $216 per night from Jul 3 to Jul 4
$216
$281 total
includes taxes & fees
Jul 3 - Jul 4
9/10 Wonderful! (2,140 reviews)
Great for an overnight stay
"Room was extremely small. Did not appreciate that there were 2 towers, one practical and lower end; the other with larger rooms more amenities and higher end. I did not realize there was a difference in types of rooms until I had reserved the room. However, it was a comfortable room very comfortable ..."

Reviewed on Jun 2, 2024

Omni Boston Hotel at the Seaport
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 $182 per night from Jul 4 to Jul 5
$182
$247 total
includes taxes & fees
Jul 4 - Jul 5
8.8/10 Excellent! (2,681 reviews)
"Front desk staff are very helpful and cheery!"

Reviewed on Jun 1, 2024

Omni Parker House
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 $143 per night from Jun 16 to Jun 17
$143
$167 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,513 reviews)
"Best property to stay at in Boston. Absolutely immaculate. You can walk anywhere from hotel."

Reviewed on Jun 3, 2024

The Revolution Hotel
See all 3,195 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

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 $534. 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 vacation 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 Center 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 vacation?
Travelers 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. Vacationing 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 vacation 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 vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation 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.

Discover the most popular places to visit in Winter Hill

Image for Fenway Park

Fenway Park

4.5/5(2,499 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(1,966 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 Boston Common

Boston Common

4.5/5(4,786 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

Image for Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
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

$30
Per adult
98% of travellers recommend
Bewitched Walking Tour of Salem
Image for Freedom Trail: Small Group Tour of Revolutionary Boston

Freedom Trail: Small Group Tour of Revolutionary Boston

$39
Per adult
100% of travellers recommend
Freedom Trail: Small Group Tour of Revolutionary Boston
See all activities in Boston

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