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.
Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,472, price is now CA $995 per person
CA $995
per person
Aug 27 - Aug 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,311, price is now CA $1,412 per person
CA $1,412
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
Location

Reviewed on Jul 5, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,809, price is now CA $1,203 per person
CA $1,203
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Simply excellent in all aspects.

Reviewed on Jul 2, 2026

Ashworth by the Sea

Ashworth by the Sea

3 out of 5
Hampton Beach
Price was CA $2,553, price is now CA $1,721 per person
CA $1,721
per person
Aug 5 - Aug 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Boston (BOS)
8.2/10 Very good! (1,331 reviews)
Property has a lot of plus side. Downsides are restaurant has gone way down hill since last year. Menu bare minimum and food was terrible. Understaffed as we had a 2.5 hour dinner waiting for seating service and waiting to pay bill. Only 2 waitstaff on duty for July 3 and maybe 3 on July 4th when hotel was booked solid. Prices are ridiculously high for such poor quality. Breakfast restaurant, which has great food but is so small we never got in by closing time. Poorly run establishment. Won’t be back.

Reviewed on Jul 5, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $3,611, price is now CA $2,537 per person
CA $2,537
per person
Sep 17 - Sep 20
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

Ready to book your vacation to Winthrop?

 

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Winthrop Hotel Deals

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
The price is CA $216 per night from Aug 2 to Aug 3
CA $216
CA $293 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,413 reviews)
"Out stay was perfect. The staff were friendly and the amenities were just what we hoped for."

Reviewed on Jul 5, 2026

Hyatt Regency Boston/Cambridge
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Jul 26 to Jul 27
CA $268
CA $361 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (4,523 reviews)
"Excellent location in Boston! Very short Uber from Boston Logan International airport. We easily walked from Seaport to Long Wharf. There was great shopping and cute cafes along the way. Our room had a water view, which I highly recommend."

Reviewed on Jul 5, 2026

Seaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Aug 2 to Aug 3
CA $226
CA $263 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (2,713 reviews)
"We stayed in Boston for one night and it was hard to find somewhere cost effective. Therefore, we opted for this hotel on a whim, never using a shared bathroom before so we were a bit apprehensive. We were so pleasantly surprised at the room, it was very well thought out on the design and layout. ..."

Reviewed on Jul 5, 2026

The Revolution Hotel
See all 4,210 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

Stay near popular Winthrop attractions

A lighthouse with a red, white, and blue top, a beach, and a town with houses.
Photo by The Curious Zephyr
Open Photo by The Curious Zephyr

Winthrop Beach

8.4/10 (26 reviews)
Why not spend a lazy afternoon at Winthrop Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.
See properties

What to do in Winthrop

Boston Hop-On Hop-Off Trolley Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

CA $73
per adult
90% of travellers recommend
Boston Old Town Trolley Hop-on Hop-Off City Tour
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

CA $119
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

CA $39
per adult
88% 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 $995 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.

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.