Winthrop Holidays

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Top hotels in Winthrop

citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
The price is S$240 per night from 30 Mar to 31 Mar
S$240
includes taxes & fees
30 Mar - 31 Mar
9.4/10 Exceptional! (879 reviews)
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Reviewed on 22 Mar,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 S$295 per night from 30 Mar to 31 Mar
S$295
includes taxes & fees
30 Mar - 31 Mar
9/10 Wonderful! (4,937 reviews)
Good room, good staff, good location.
"Excellent desk staff, friendly and helpful and professional. Room was quiet, clean, spacious, and nicely furnished. I really appreciated having control of the thermostat in my room, and could even open the windows for fresh air!"

Reviewed on 23 Mar,2025

Harborside Inn Of 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 S$237 per night from 31 Mar to 1 Apr
S$237
includes taxes & fees
31 Mar - 1 Apr
8.6/10 Excellent! (1,968 reviews)
"I wasn't sure going in that I'd like the communal bathroom setup, but thought I'd give it a try for a new experience. It was surprisingly not bad at all. The staff kept the stalls very clean and they provide shower bags for each guest in your room. Overall very pleasant experience!"

Reviewed on 17 Mar,2025

The Revolution Hotel
See all 3,735 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 holiday package cost?
You can grab a holiday package to this top destination 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.

Popular places to visit

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

Fenway Park

4.5/5(61 reviews)

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

Fenway Park
Harvard University featuring a city and heritage architecture

Harvard University

4.5/5(102 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
New England Aquarium

New England Aquarium

4.5/5(57 reviews)

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

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

S$105
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

S$33
per adult
80% of travellers recommend
View Boston Observation Deck Admission Tickets
BEST New York City Day Tour from Boston

New York City Day Tour from Boston

S$228
per traveller
New York City Day Tour from Boston
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.