Winthrop Vacations from $895

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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.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was $1,400, price is now $895 per person
$895
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (3,191 reviews)
Good location staff were great

Reviewed on Jun 24, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $3,246, price is now $1,808 per person
$1,808
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,324, price is now $1,355 per person
$1,355
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (711 reviews)
It would be nice to include bottled water in the room. Expected a little more for paying $1k/nt. Staff were courteous. The shuttle is helpful and convenient to airport.

Reviewed on Jun 19, 2026

The Coach House

The Coach House

3 out of 5
Save 100% on your flight
Price was $1,826, price is now $1,087 per person
$1,087
per person
Sep 5 - Sep 8
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (182 reviews)
Everything was perfect

Reviewed on Jun 12, 2026

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Price was $1,517, price is now $975 per person
$975
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (5,092 reviews)
This hotel was perfect. Upon arrival we were greeted by a very friendly staff, especially Arbon and Ardit. We arrived before normal check in but they found a room for all of us and we were settling in within minutes of our arrival. Every team member we met, were friendly and professional, including the cafe staff. Ardit seemed to be everywhere. He worked the front desk upon arrival and was a bartender at night. Arbon and Ardit were very quick to make restaurant reservations and all proved to be excellent. Upon departure, Arbon arranged for transportation for us to the airport. The rooms were immaculate and the location of the hotel was terrific. We would definitely stay here again.

Reviewed on Jun 26, 2026

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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

8.4/5 (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
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Tour of Historic Fenway Park, America's Most Beloved Ballpark

$45
per adult
98% of travellers recommend
Tour of Historic Fenway Park, America's Most Beloved Ballpark
Harvard Guide leading a tour

Harvard University Campus Guided Walking Tour

$23
per adult
92% of travellers recommend
Harvard University Campus Guided Walking Tour
See all activities in Winthrop

Winthrop Hotel Deals

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $167 total per night from Jun 30 to Jul 1
$167 total
Jun 30 - Jul 1
Total with taxes and fees
9/10 Wonderful! (2,700 reviews)
"Interesting , unique hotel in a nice neighborhood"

Reviewed on Jun 26, 2026

The Revolution Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
$193 nightly
The price is $224 total per night from Jul 1 to Jul 2
$224 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (2,392 reviews)
"Loved the room layout and high ceilings. The restaurant in the hotel was excellent too."

Reviewed on Jun 27, 2026

Hyatt Regency Boston/Cambridge
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$219 nightly
The price is $254 total per night from Jul 5 to Jul 6
$254 total
Jul 5 - Jul 6
Total with taxes and fees
9.6/10 Exceptional! (4,477 reviews)
"Hotel was lovely. Room had everything in it you needed. Walking distance to Downtown Boston."

Reviewed on Jun 27, 2026

Seaport Hotel Boston
See all 4,206 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 $895 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.