Winthrop Vacations from $536
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Boston Lodge and Suites
Dorchester
$536
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Boston Harbor Hotel
North End
$1,136
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,011 reviews)
Wow. Just wow. What a stay. Fantastic hotel well looked after. Amazing staff so friendly and welcoming. Great location. A fabulous stay couldn’t recommend more.
Reviewed on Sep 2, 2026
Iris Hotel Boston
Coolidge Corner
$724
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (676 reviews)
This was our second stay here. Love the location and how close it is to the green line stop. Room was very comfortable and we appreciate the full fridge and microwave. perhaps my only suggestion is to put some bare essential dishes/utensils in the room.
As usual the staff were attentive to our needs, friendly and efficient. Special shout out to "Alexa" at the front desk. I forgot something in my car, and she went with me to the garage, so I was not alone since it was at night. Thank you also to the valet drivers. We had to leave at 3am on the day of our departure and they made sure our car was ready to go! Last but not least, we ate at the restaurant this time and the food was delicious! Thank you for your excellent customer service. We had a very enjoyable stay for college move-in!
Reviewed on Sep 3, 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 Boston?
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
Seaport Hotel Boston
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
$254 total
Sep 20 - Sep 21
Total with taxes and fees
9.6/10 Exceptional! (4,934 reviews)
"Seaport is in a great spot. Close to the harbor and not to far from downtown Boston."
Reviewed on Sep 3, 2026
The Revolution Hotel
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$148 nightly
$173 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (2,883 reviews)
"Clean bathrooms"
Reviewed on Sep 2, 2026
Harborside Inn Of Boston
185 State St Boston MA
$219 nightly
$255 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (6,949 reviews)
"Great location for us. Easy Metro access to get all around Boston. When not on Metro tons of food and pub options walking distance. Room was large and recently remodeled and comfortable"
Reviewed on Sep 2, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Winthrop vacation package cost?
You can grab a vacation package to this top destination from $536 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.
Explore a world of travel with Expedia
- Granary Burying Ground
- Waterfront Promenade Park
- Printing Office of Edes and Gill
- Kendall Square
- Copp's Hill Burying Ground
- Rowes Wharf
- George Washington Statue
- Salem Vacations
- Longfellow Bridge
- Statue of Paul Revere
- Harpoon Brewery
- Leader Bank Pavilion
- Norman B. Leventhal Park
- Paul Revere House
- East Boston Memorial Stadium
- Charles Hayden Planetarium
- Old State House
- New England Aquarium
- The Shops at Prudential Center
- Isabella Stewart Gardner Museum
- Charlestown Navy Yard
- Charlestown Navy Yard Visitor Center
- Boston Massacre Site
- Theatre District Vacations
- New England Sports Museum
- Harvard Museum of Natural History
- Newbury Street
- Naval Hospital Boston Historic District
- Old North Church
- Prudential Tower
- Rose Fitzgerald Kennedy Greenway
- Faneuil Hall Visitor Center
- Breed's Hill
- Massachusetts State House
- Museum of Science
- Charles River Esplanade
- Blackstone Block Historic District
- Boston Children's Museum
- Stata Center
- Suffolk University
- Deer Island HarborWalk
- Boston National Historical Park
- Boston City Hall Plaza
- Revere Vacations
- Chelsea Vacations
- Harborwalk
- Church of the Covenant
- Seaport World Trade Center
- Long Wharf
- Cambridgeside Galleria
- Boston Harbor
- Copley Square
- Rumney Marsh Reservation
- Fort Point Arts Community
- Boston Symphony Hall
- Encore Boston Harbor
- Fenway Park
- Institute of Contemporary Art
- Charlestown Vacations
- Innovation District
- Robert Gould Shaw Memorial
- Belle Isle Marsh Reservation
- Hammond Castle
- Benjamin Franklin Statue
- Flynn Cruiseport Boston
- Boston Tea Party Ship
- Castle Island
- Orpheum Theater
- Wingaersheek Beach
- All Saints Way
- Quincy Market
- Chelsea Garden Cemetery
- Td Garden
- Old South Meeting House
- Boston Common
- Boston Museum of Fine Arts
- Bunker Hill Monument
- Louisburg Square
- Old South Church
- Liberty Wharf
- Massachusetts General Hospital
- Boston Public Garden
- Seaport Common
- Massachusetts Institute of Technology
- Seaport District Vacations
- New England Holocaust Memorial
- Trinity Church Boston
- The Freedom Trail
- Revere Beach
- Old Corner Bookstore
- King's Chapel
- Boston Convention and Exhibition Center
- Faneuil Hall Marketplace
- Zakim Bunker Hill Bridge
- Boston Vacations
- Downtown Boston Vacations
- Memorial Hall
- Assembly Row
- Irish Heritage Trail
- Park Street Church
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
