Winthrop Vacations from $293

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Your Winthrop Vacation

There's no better way to escape than with one of our vacation packages to Winthrop. The rich history and coastal scenery are a couple of the countless reasons to visit this captivating city. Fill your free time with tours of Boston Common, Faneuil Hall Marketplace and Copley Place, some of the top attractions you simply have to see during your trip to Winthrop. Check out Expedia's extensive range of travel options and start planning your ideal vacation to Winthrop now.

The Latest Winthrop vacation packages

Price found within the past 48 hours. Click for updated prices.
Even Hotels Manchester Airport by IHG
Motel 6 Danvers, MA - Boston North
Raffles Boston
DoubleTree by Hilton Boston North Shore
Fairfield Inn & Suites by Marriott Plymouth
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Winthrop Hotel Deals

citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $203 total per night from Aug 24 to Aug 25
$203 total
Aug 24 - Aug 25
Total includes taxes and fees
9.2/10 Wonderful! (3,682 reviews)
"Great property. Interesting and unique."

Reviewed on Aug 19, 2025

citizenM Boston North Station
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $194 total per night from Sep 1 to Sep 2
$194 total
Sep 1 - Sep 2
Total includes taxes and fees
9.6/10 Exceptional! (3,248 reviews)
"This was not the least expensive option, but I certainly got what I paid for. People were just so nice. It was easy to get too easy to get around, just perfect."

Reviewed on Aug 17, 2025

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
$264 nightly
The price is $307 total per night from Aug 24 to Aug 25
$307 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (3,843 reviews)
"We loved the rooftop pool!"

Reviewed on Aug 18, 2025

Omni Boston Hotel at the Seaport
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.

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Frequently asked questions

How much does a Winthrop vacation package cost?
You can grab a vacation package to this top destination from $293 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?
You can generally find lower prices and greater availability in December, January and February. Browse our cheap Winthrop vacation packages and you could get some excellent off-season deals.
How many days is enough for Winthrop?
You can easily explore all the main sights in Winthrop in a few days, including the popular Winthrop Shore Reservation. If you want an extended Winthrop vacation, check out what sort of day tours and activities are available nearby.
Is it worth booking a vacation package to Winthrop?
Winthrop offers everything you need for an unforgettable trip. Get your Winthrop vacation off to a flying start by visiting popular attractions like Winthrop Beach.
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. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Winthrop.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the largest expense during your trip to Winthrop.
  3. Organize your Winthrop getaway with Expedia's trip planning tool: Search for and book hotels and activities all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Winthrop together.
  4. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Winthrop. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Winthrop vacation package.
  6. Book activities and experiences ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on the highlights of Winthrop. Find all the incredible things to do in Winthrop with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Winthrop vacation packages?
Your Winthrop getaway is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.