Winthrop Vacation Packages

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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.

Top Winthrop Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
per person
Sep 4 - Sep 8
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Save 100% on your flight
per person
Sep 25 - Sep 28
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
It was a pleasant stay. The staffs were friendly. The room had both microwave and fridge. Although the room was neat, the cleaners did miss a couple of things.

Reviewed on Jun. 29, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Save 100% on your flight
per person
Sep 25 - Sep 30
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (135 reviews)
Nobody on property to talk to

Reviewed on May 20, 2025

Ready to book your vacation to Winthrop?

 

Choose your dates

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 CA $289 per night from Aug 10 to Aug 11
CA $289
CA $393 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (3,667 reviews)
"The hotel was clean and staff was friendly."

Reviewed on Jul. 12, 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 CA $252 per night from Jul 13 to Jul 14
CA $252
CA $293 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"Always a great stay"

Reviewed on Jul. 11, 2025

citizenM Boston Back Bay
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is CA $282 per night from Jul 13 to Jul 14
CA $282
CA $329 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (5,302 reviews)
"this property was perfect for our stay in Bostain. First of all the room was large, clean and very comfortable. The front desk staff was very pleasant. The best part about this hotel is the location. You are on the waterfront and within walking distance of everything you need including many tours. ..."

Reviewed on Jul. 10, 2025

Harborside Inn Of Boston
See all 3,776 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Winthrop

Fenway Park featuring a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(305 reviews)

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

Fenway Park
Harvard University which includes a city and heritage architecture

Harvard University

4.5/5(279 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 which includes flowers, a garden and landscape views

Boston Common

4.5/5(518 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

CA $108
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

CA $75
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

CA $47
per adult
84% of travellers recommend
View Boston Observation Deck Admission Tickets
See all activities in Winthrop

Frequently asked questions

How much does a Winthrop vacation package cost?
Offering great value package deals from CA $819 on Expedia, you'll be surprised at how little a vacation to Winthrop costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winthrop?
Plan your trip for the off-peak season and you're likely to score cheap Winthrop vacation packages. Remember that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Winthrop?
With about 2 days, you'll have enough time to experience popular neighbourhoods like South Boston and D Street - West Broadway during your Winthrop vacation. Remember to also add Copley Square and New England Aquarium to your must-see list. Looking for more adventures? Consider exploring outside of Winthrop on day trips and tours.
Is it worth booking a vacation package to Winthrop?
Winthrop is a good vacation destination with attractions like Winthrop Beach among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Winthrop vacation promises a good time for everyone.
How to find the best Winthrop package deals?
Begin your search for a Winthrop package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Winthrop package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winthrop escape underway.
Is it cheaper to book a Winthrop vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a tailored Winthrop vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Winthrop?
If you have your Winthrop vacation dates confirmed, book early to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Winthrop?

  1. Pick your dates: The things you want to do in Winthrop and your preferred season can help you decide when to go.
  2. Set a budget: Factor in costs such as flights, meals and transportation when working out how much to set aside for your trip to Winthrop. Then, select a hotel that fits your budget, whether that's an affordable option or a swankier getaway.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Winthrop. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Winthrop vacation package that brings all your bookings together.

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