Winthrop Trips (flight + hotel)

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Top hotels in Winthrop

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 P10,931 per night from Jul 19 to Jul 20
P10,931
P15,059 total
Jul 19 - Jul 20
includes taxes & fees
9/10 Wonderful! (3,563 reviews)
"Great for convention attendees - but I wasn't"

Reviewed on Jun 19, 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 P11,128 per night from Jun 29 to Jun 30
P11,128
P14,674 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very Good! (1,117 reviews)
"Pleasant and attentive employees from the front desk to the restaurant, bar and cleaning staff. They were able to retrieve my phone charger (as I had left it in the room) 4 hours after check out. Kindly held our bags prior to departure. Great location and view from our room. I would definitely recommend ..."

Reviewed on Jun 22, 2025

Hilton Boston Back Bay
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 P8,186 per night from Jun 29 to Jun 30
P8,186
P9,533 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,283 reviews)
"Our room has a weird noise associated with A/C. And it only occurred on the 3rd night. Bothered too much so had to switch to a new room"

Reviewed on Jun 22, 2025

citizenM Boston Back Bay
See all 3,743 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 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.

Popular places to visit

Harvard University which includes heritage architecture and a city

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
New England Aquarium

New England Aquarium

From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips.

New England Aquarium
Massachusetts showing outdoor eating, a house and cafe lifestyle

Newbury Street

Stretching between Massachusetts Avenue and Boston Public Gardens, this upscale street is one of Boston’s most popular shopping and dining destinations.

Newbury Street

What to do in Winthrop

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

P4,438
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

P3,942
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

P1,898
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.