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.
The Boxer

The Boxer

4 out of 5
West End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
8.6/10 Excellent! (1,236 reviews)
This hotel is super cute. Our room was pretty tiny but the proximity to the TD Garden is what makes this the real winner. If you are super sensitive to noise the water running through the pipes is quite loud. It never woke me up but it was annoying when we were relaxing in our room. As far as noise goes, we never heard anyone in the hallway.

Reviewed on Jul. 22, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Everything was amazing, room was exactly like it’s shown in the photos. Will definitely recommend and return. Thank you

Reviewed on Jul. 26, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Friendly and professional service and care. Great location to walk to every site you need to get to. Staff especially Will and Howard (door men) always friendly and asked if you needed anything Thanks to the staff you made our first but not our last stay amazing

Reviewed on Jul. 25, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 18 - Sep 21
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Boston (BOS)
9.4/10 Exceptional! (349 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul. 20, 2025

Ready to book your vacation to Winthrop?

 

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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 $251 per night from Aug 24 to Aug 25
CA $251
CA $348 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (3,716 reviews)
"This property is in a perfect location in the Seaport. We loved it!"

Reviewed on Jul. 24, 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 $259 per night from Aug 10 to Aug 11
CA $259
CA $302 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,496 reviews)
"I like almost everything but breakfast was not good and fruit was not fresh. Also bar does not serve good food so there is a room for huge improvement in this area."

Reviewed on Jul. 26, 2025

citizenM Boston Back Bay
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
The price is CA $238 per night from Aug 24 to Aug 25
CA $238
CA $278 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (3,592 reviews)
"Great location, very quiet and friendly staff"

Reviewed on Jul. 26, 2025

citizenM Boston North Station
See all 3,784 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

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

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

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 $96
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 $46
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 $935 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.