Winthrop Vacations

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Find the Best Winthrop Vacation Packages

Winthrop Hotel Deals

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 ₩312,929 per night from Jul 19 to Jul 20
₩312,929
₩419,575 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,624 reviews)
"Great experience. The fact that we could check into our room at 10:30am when we arrived was HUGE! Did not lose any time on our very quick vacation."

Reviewed on Jul 1, 2025

Omni Boston Hotel at the Seaport
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 ₩235,509 per night from Jul 6 to Jul 7
₩235,509
₩274,251 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,319 reviews)
"Location was great!"

Reviewed on Jun 28, 2025

citizenM Boston Back Bay
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 ₩320,780 per night from Jul 2 to Jul 3
₩320,780
₩380,316 total
Jul 2 - Jul 3
includes taxes & fees
9.6/10 Exceptional! (2,996 reviews)
"Staying at the seaport hotel was a great location. It was within walking distance to shopping and sight seeing. Parking was very convenient and accessible. I highly recommend staying there."

Reviewed on Jun 30, 2025

Seaport Hotel Boston
See all 3,772 properties in Winthrop
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 Winthrop vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Winthrop costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Winthrop?
To score cheap Winthrop vacation packages, organize your getaway outside of peak periods like public holidays and major events. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Winthrop?
Generally, a handful of days is great for a Winthrop vacation. With a well-organized schedule, you can see all the leading attractions including Winthrop Shore Reservation, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Winthrop?
It's no wonder a Winthrop vacation is on the must-do list of many travelers. Top attractions like Winthrop Beach are just the start of things to keep you busy here.
How to find the best Winthrop package deals?
Start your search for a Winthrop package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winthrop package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winthrop escape off to a flying start.
Is it cheaper to book a Winthrop vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize your Winthrop escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Winthrop?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Winthrop getaway.
How to plan a trip to Winthrop?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to travel to Winthrop.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Winthrop.
  3. Decide your trip length: Consider how long you'd like to spend discovering Winthrop. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Winthrop vacation package for you.

Discover the most popular places to visit in Winthrop

Fenway Park which includes 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 showing 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 featuring marine life

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