Winthrop Holidays

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Top Flight + Hotel Deals in Winthrop

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

YOTEL Boston

4 out of 5
Seaport District
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Tiny hotel rooms! Convenient for a quick business trip 1 or 2 days. Anything longer, send extra for more space.

Reviewed on 31 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
18 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
The bed and room were very comfortable with a lovely view. The gym was fabulous. The restaurant has a very limited menu with few to none green simple salad option or vegetables-all the meals we chose were well prepared with good service but pricey.

Reviewed on 1 Aug 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
per person
1 Sept - 8 Sept
found 8 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,009 reviews)
Beautiful hotel located right in the heart of the city! Nice big room with a big bathroom. Located near all the shopping and great restaurants. Also very close to the T station and very safe!

Reviewed on 28 Jul 2025

Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
per person
1 Sept - 8 Sept
found 8 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (234 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
per person
1 Sept - 8 Sept
found 8 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.4/10 Good! (114 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on 23 May 2025

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 €223 per night from 24 Aug to 25 Aug
€223
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (3,769 reviews)
"Was pleasantly surprised, great hotel and staff."

Reviewed on 28 Jul 2025

Omni Boston Hotel at the Seaport
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 €177 per night from 24 Aug to 25 Aug
€177
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (3,610 reviews)
CitizenM never disappoints!
"I love CitizenM and the one in Boston didn't disappoint. The check in staff (it is self check-in, but they always come over to help) and the staff in the "canteen" were wonderfully friendly to a tired traveler."

Reviewed on 29 Jul 2025

citizenM Boston North Station
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 €193 per night from 10 Aug to 11 Aug
€193
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,534 reviews)
"Loved this property! Only negative part was the actual bed. Very hard in the middle of the night to use bathroom when you have to jump over your partner to get out of the bed. Otherwise very clean!!"

Reviewed on 1 Aug 2025

citizenM Boston Back Bay
See all 3,782 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.

Popular places to visit

Fenway Park showing night scenes and a sporting event 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 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

What to do in Winthrop

Narrated Sunset Cruise of Boston Harbor

Narrated Sunset Cruise of Boston Harbor

€25
per adult
84% of travellers recommend
Narrated Sunset Cruise of Boston Harbor
Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

€68
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
The top floor of View Boston - 360 degree indoor observation deck

View Boston Observation Deck Admission Tickets

€29
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 holiday package cost?
You can grab a holiday package to this top destination from €818 on Expedia. However, how much your holiday 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 holiday packages, organise 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 holiday. With a well-organised 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 holiday package to Winthrop?
It's no wonder a Winthrop holiday is on the must-do list of many travellers. 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise 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 holiday 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, favourite 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 accommodation 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 accommodation: After you've nailed down your trip dates and duration, book the ideal Winthrop holiday package for you.

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