Winthrop Vacations from $489
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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.
Four Seasons Hotel Boston
Bay Village
$1,227
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in.
On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.
Reviewed on Oct 6, 2026
Raffles Boston
Back Bay
$1,187
per person
Dec 26 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Boston (BOS)
9.6/10 Exceptional! (332 reviews)
A stunning hotel with super helpful staff. Would highly recommend the Raffles, from start to finish it was excellent and we’ll definitely be back.
Reviewed on Oct 14, 2026
Stay near popular Winthrop attractions
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.
Photo by The Curious Zephyr
Winthrop Shore Reservation
7.6/10 (5 reviews)
This Atlantic coastal retreat offers a mix of sandy and pebbly shores with stunning Boston skyline views. Enjoy morning walks along the promenade when the beach is serene and the sea breeze most refreshing.
Point Shirley Beach
8.0/10 (7 reviews)
Why not spend a lazy afternoon at Point Shirley Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.
Donovan Beach
7.6/10 (4 reviews)
This intimate sandy spot offers stunning Boston skyline views and a unique vantage point for watching planes from Logan Airport. Bring a picnic to enjoy while aircraft soar dramatically overhead.
What to do in Winthrop
Boston CityPASS®: Admission to Top 4 Attractions
$84
per adult
92% of travellers recommend
Boston Haunted Tour : Ghosts & Gravestones
$46
per adult
80% of travellers recommend
City Cruises Boston: Historic Sightseeing Cruise
$37
per adult
92% of travellers recommend
Winthrop Hotel Deals
Omni Boston Hotel at the Seaport
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$298 nightly
$347 total
Nov 11 - Nov 12
Total with taxes and fees
9.2/10 Wonderful! (4,909 reviews)
"Things were fine but"
Reviewed on Oct 15, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
$167 total
Nov 8 - Nov 9
Total with taxes and fees
9/10 Wonderful! (2,970 reviews)
"Second time staying here - was in a double room last time with a friend and that was great - the single room very tight - the sink too small to really use without getting water all over. no chair or luggage rack. Clean and sparse. Liked that they had a small gym downstairs. Nice area & close to Boston ..."
Reviewed on Oct 15, 2026
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
$254 total
Oct 30 - Oct 31
Total with taxes and fees
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 $489 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
