Winthrop Vacations from $410

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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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $649, price is now $410 per person
$410
per person
May 2 - May 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Great clean room that was nice and warm on the cold day. Loved the fireplace in the living area and the bed was very comfortable and cozy. Great value for the space we got!

Reviewed on Feb 8, 2026

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $1,087, price is now $688 per person
$688
per person
May 2 - May 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,241 reviews)
Clean & unique concept of a stay. Really enjoyed my stay. Will definitely be staying here again.

Reviewed on Feb 9, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,191, price is now $763 per person
$763
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,461, price is now $947 per person
$947
per person
May 2 - May 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,300, price is now $850 per person
$850
per person
May 2 - May 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Thank you for the cool corner suite on the 9th floor! We stayed over after attending a Bruins game. Short stay but nice place. Good location for our adventures. We’ll stay again if when we are back in Boston! Ty

Reviewed on Jan 29, 2026

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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

Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $160 total per night from Feb 22 to Feb 23
$160 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (3,117 reviews)
Location

Reviewed on Feb 6, 2026

Hilton Boston Park Plaza
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$119 nightly
The price is $139 total per night from Feb 16 to Feb 17
$139 total
Feb 16 - Feb 17
Total with taxes and fees
9.2/10 Wonderful! (6,219 reviews)
Nice staff, great room and bathroom and location is easy to walk everywhere. One of the hotels with a cheaper parking rate as well which is a plus.

Reviewed on Feb 6, 2026

Harborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Feb 10 to Feb 11
$104 total
Feb 10 - Feb 11
Total with taxes and fees
9/10 Wonderful! (2,450 reviews)
I stayed in a loft on the side of the main hotel, and it was extremely spacious with all the amenities I needed. It was definitely worth the price, especially given the beautiful area it’s located in. I didn’t interact much with the staff, but the few interactions I had were very pleasant. I would ...

Reviewed on Feb 7, 2026

The Revolution Hotel
See all 4,263 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

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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 $410 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.

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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.