Winthrop Vacations from $542

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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.

The Latest Winthrop vacation packages

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was $772, price is now $542 per person
$542
per person
Jan 8 - Jan 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
Perfect location! Excellent staff. Not a fan of the service in the restaurant, but the food was amazing as well as the bartender.

Reviewed on Nov 1, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $2,094, price is now $921 per person
$921
per person
Dec 15 - Dec 22
found 1 hour ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
8.4/10 Very Good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,714, price is now $1,094 per person
$1,094
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Lovely for a romantic stay

Reviewed on Oct 31, 2026

The Atlas Hotel Boston Cambridge

The Atlas Hotel Boston Cambridge

4.5 out of 5
Allston
Price was $2,545, price is now $1,768 per person
$1,768
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Boston (BOS)
9.4/10 Exceptional! (464 reviews)

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Price was $1,690, price is now $1,236 per person
$1,236
per person
Dec 15 - Dec 22
found 1 hour ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
8/10 Very Good! (13 reviews)

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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)
This tranquil stretch of shoreline offers panoramic views of Boston's skyline across the Atlantic. Stroll the promenade at sunrise when the soft sand and gentle waves create a perfect coastal escape.
See properties

What to do in Winthrop

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$84
per adult
92% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Ghosts and Gravestones Tour guides in costume in Boston

Boston Haunted Tour : Ghosts & Gravestones

$46
per adult
80% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

$37
per adult
92% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
See all activities in Winthrop

Winthrop Hotel Deals

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $223 total per night from Nov 22 to Nov 23
$223 total
Nov 22 - Nov 23
Total with taxes and fees
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $131 total per night from Nov 23 to Nov 24
$131 total
Nov 23 - Nov 24
Total with taxes and fees
The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $192 total per night from Nov 23 to Nov 24
$192 total
Nov 23 - Nov 24
Total with taxes and fees
Seaport Hotel Boston
See all 4,141 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.

Find the Best Winthrop Vacation Packages

Winthrop Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Logan Intl. Airport (BOS)
Population
17,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
New England Aquarium, Boston Museum of Fine Arts and Revere Beach

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Frequently asked questions

How much does a Winthrop vacation package cost?
You can grab a vacation package to this top destination from $542 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?
You can generally find lower prices and greater availability in December, January and February. Browse our cheap Winthrop vacation packages and you could get some excellent off-season deals.
How many days is enough for Winthrop?
You can easily explore all the main sights in Winthrop in a few days, including the popular Winthrop Shore Reservation. If you want an extended Winthrop vacation, check out what sort of day tours and activities are available nearby.
Is it worth booking a vacation package to Winthrop?
Winthrop offers everything you need for an unforgettable trip. Get your Winthrop vacation off to a flying start by visiting popular attractions like Winthrop Beach.
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. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Winthrop.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the largest expense during your trip to Winthrop.
  3. Organize your Winthrop getaway with Expedia's trip planning tool: Search for and book hotels and activities all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Winthrop together.
  4. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Winthrop. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Winthrop vacation package.
  6. Book activities and experiences ahead of time: Whether it's entrance to a major attraction or a day trip in nature, you won't have to worry about missing out on the highlights of Winthrop. Find all the incredible things to do in Winthrop with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Winthrop vacation packages?
Your Winthrop getaway is meant to be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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