Winthrop Vacations from $587

Book a Hotel + Flight or Car together to unlock savings

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.
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
Coolidge Corner
Price was $900, price is now $587 per person
$587
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (3,743 reviews)
Great stay! Staff are really nice.

Reviewed on Mar 2, 2026

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
Price was $1,309, price is now $891 per person
$891
per person
May 24 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (3,135 reviews)
Very friendly and helpful staff. Terrific location. Clean and comfortable rooms. Highly recommend!

Reviewed on Mar 1, 2026

Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Downtown Boston
Price was $1,624, price is now $1,126 per person
$1,126
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,381 reviews)
Staff was terrific! We had to extend our stay due to the blizzard and everyone including housekeepers were awesome!!

Reviewed on Feb 27, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was $1,499, price is now $1,041 per person
$1,041
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Everything was perfect! No complain.

Reviewed on Mar 1, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,032, price is now $720 per person
$720
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winthrop
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Discover the most popular places to visit in Winthrop

Nighttime baseball game at Fenway Park showcasing a vibrant atmosphere in Boston, Massachusetts

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

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

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

Gillette Stadium
Boston Common showcases lush greenery and city skyline under a clear blue sky during a sunny day

Boston Common

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

What to do in Winthrop

Zac tells a story about the John Harvard statue

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
100% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
See all activities in Winthrop

Winthrop Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $182 total per night from Mar 8 to Mar 9
$182 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (4,024 reviews)
Staff were exceptionally helpful and pleasant. Loved our stay

Reviewed on Mar 2, 2026

Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $214 total per night from Mar 8 to Mar 9
$214 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (4,479 reviews)
Difficulty turning Shower handle & was unable to turn on hot water on & had to take an ice cold shower on my last nite. Room as configuration was small but clean. Not sure if my military and/or AARP discount was applied on this 3 nite stay at Omni hotel as rate was 233.80 per nite. Not great on a ...

Reviewed on Mar 2, 2026

Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $183 total per night from Mar 22 to Mar 23
$183 total
Mar 22 - Mar 23
Total with taxes and fees
8.4/10 Very Good! (3,112 reviews)
Yes the room was very clean. And very comfortable for a small room. The shower's tight. I think that is the only Town side to the wicked small room. I stay here a lot. The staff is always top notch. Love the little sitting room with the fire it's. Very uncomfortable. Always enjoy staying here.

Reviewed on Mar 2, 2026

Hilton Boston Park Plaza
See all 4,244 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.

Find the Best Winthrop Vacation Packages

Winthrop Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
17,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winthrop vacation package cost?
You can grab a vacation package to this top destination from $587 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.

Explore a world of travel with Expedia

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