Winthrop Vacations from ￥240,492

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

The Latest Winthrop Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
per person
Sep 6 - Sep 12
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,025 reviews)
The location is great and the staff very helpful and friendly. The Patio and craft beer place on location are lovely.

Reviewed on Jun 22, 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
per person
Sep 6 - Sep 12
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (224 reviews)
Beautiful and comfortable boutique hotel experience!

Reviewed on May 23, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
per person
Sep 6 - Sep 12
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
7.4/10 Good! (84 reviews)
Very cozy and centrally located. Satellite tv didn’t work.

Reviewed on May 28, 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
per person
Sep 6 - Sep 12
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
7.4/10 Good! (112 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on May 23, 2025

The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
Sep 6 - Sep 12
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
7.4/10 Good! (620 reviews)
The hotel is convenient to the T which makes getting downtown and to Fenway easy. It’s an older hotel and could use some updating.

Reviewed on Jun 20, 2025

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 ￥27,932 per night from Jul 19 to Jul 20
￥27,932
￥38,482 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,574 reviews)
"Nice stay and atmosphere in the lobby"

Reviewed on Jun 21, 2025

Omni Boston Hotel at the Seaport
Hilton Boston Back Bay
Hilton Boston Back Bay
4 out of 5
40 Dalton St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥28,436 per night from Jun 29 to Jun 30
￥28,436
￥37,497 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very Good! (1,116 reviews)
"Short business trip. Did a lot of writing/teleconferences from room and the Internet was good. Quiet (21st floor) and conveniently located. Used the heath club and the facilities were good."

Reviewed on Jun 20, 2025

Hilton Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is ￥20,679 per night from Jul 2 to Jul 3
￥20,679
￥24,080 total
Jul 2 - Jul 3
includes taxes & fees
8.4/10 Very Good! (3,710 reviews)
Exactly what I was looking for
"Convenient location, friendly front desk staff. Called ahead of time to confirm my reservation and the person I spoke with was courteous and professional. Didn't use any of the amenities so can't comment there. Only here for a night but it met all my (admittedly basic) needs. By far the best price ..."

Reviewed on Jun 20, 2025

Copley Square Hotel, a FOUND Hotel
See all 3,721 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 from ￥240,492 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

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
Harvard University showing a city and heritage architecture

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
Boston Common featuring landscape views, a skyscraper and flowers

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

What to do in Winthrop

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

￥11,423
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

￥10,147
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

￥3,871
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Winthrop
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.