Winthrop Holidays

Book a Hotel + Flight or Car together to unlock savings

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 6.253.884 ₫ per night from 7 Aug to 8 Aug
6.253.884 ₫
8.348.317 ₫ total
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (3,626 reviews)
Great Boston Hotel!
"You need to Reserve Pool ahead they do not priorize GUEST my only complain. It goes by time slots."

Reviewed on 5 Jul 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 4.810.680 ₫ per night from 13 Jul to 14 Jul
4.810.680 ₫
5.602.037 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,387 reviews)
"Modern and convenient!"

Reviewed on 7 Jul 2025

citizenM Boston Back Bay
Copley Square Hotel, a FOUND Hotel
Copley Square Hotel, a FOUND Hotel
4 out of 5
47 Huntington Ave, Boston, MA
Fully refundableReserve now, pay when you stay
The price is 4.321.769 ₫ per night from 20 Jul to 21 Jul
4.321.769 ₫
5.032.700 ₫ total
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (3,736 reviews)
"This location was wonderful. The room was very nice and clean. Loved the nostalgic yet updated feel. Would absolutely recommend. We will be back."

Reviewed on 6 Jul 2025

Copley Square Hotel, a FOUND Hotel
See all 3,775 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 which includes a sporting event and night scenes as well as a large group of people

Fenway Park

4.5/5(61 reviews)

Catch an event at Fenway Park during your trip to Boston. Attend a baseball game in this walkable area.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

4.5/5(102 reviews)

Take a campus tour or just explore the area around Harvard University, a top university in Boston. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Harvard University
Gillette Stadium

Gillette Stadium

3/5(2 reviews)

Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's great live music and acclaimed theatre scene.

Gillette Stadium

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.