Winthrop Vacations from $496

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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.
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $685, price is now $496 per person
$496
per person
Oct 26 - Oct 30
found 20 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,029 reviews)
Hotel 1620 Plymouth Harbor offers a great location near downtown and the waterfront, with friendly staff and a family-friendly atmosphere. Rooms are spacious but can feel dated. There Overall, it’s a solid choice for convenience and amenities, though some aspects need improvement.

Reviewed on Sep 16, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $991, price is now $538 per person
$538
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Falmouth Tides

Falmouth Tides

2.5 out of 5
Falmouth Heights
Price was $829, price is now $623 per person
$623
per person
Oct 26 - Oct 31
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (646 reviews)
This is a motel. All the reviews I read said this place would be the best place to stay in Falmouth. Yes it was on the beach and yes it had a lovely view of the harbour and yes it was convenient for the ferry to MV. But it was the most expensive place we stayed and was just a motel with some beach chairs. A coffee hut outside from 7am. No coffee making facilities in room and a very basic plastic encased shower. Stunning view over the ocean but not worth the money. We used the complimentary bikes (these were a bonus) to ride to town for meal in the evening.

Reviewed on Sep 16, 2025

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

3 out of 5
Save 100% on your flight
Price was $1,462, price is now $1,113 per person
$1,113
per person
Nov 20 - Nov 25
found 7 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Boston (BOS)
No reviews
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,549, price is now $1,182 per person
$1,182
per person
Oct 26 - Oct 30
found 16 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.8/10 Excellent! (239 reviews)
The staff especially the new

Reviewed on Sep 14, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winthrop
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Discover the most popular places to visit in Winthrop

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Harvard University showing a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University
Boston Common featuring landscape views, a skyscraper and flowers

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common

What to do in Winthrop

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

$79
per adult
90% of travellers recommend
Boston CityPASS®: Admission to Top 4 Attractions
Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

$54
per adult
84% of travellers recommend
Boston Harbor Sunset Cruise
Narrated Sunset Cruise of Boston Harbor

Narrated Sunset Cruise of Boston Harbor

$29
per adult
84% of travellers recommend
Narrated Sunset Cruise of Boston Harbor
See all activities in Winthrop

Winthrop Hotel Deals

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $269 total per night from Sep 21 to Sep 22
$269 total
Sep 21 - Sep 22
Total with taxes and fees
9.6/10 Exceptional! (3,423 reviews)
"Beautiful property, location and friendly staff"

Reviewed on Sep 15, 2025

Seaport Hotel Boston
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
$274 nightly
The price is $319 total per night from Sep 21 to Sep 22
$319 total
Sep 21 - Sep 22
Total with taxes and fees
9/10 Wonderful! (3,987 reviews)
"We both said this was probably the nicest (fanciest) hotel we’ve ever stayed at. (And we’ve been. To a lot of fancy hotels). The views, the bathroom, the tiny nook to sit and do your make-up…GORGEOUS! The beds and bedding were heavenly. I already miss them. The coffee shop down stairs has the best ..."

Reviewed on Sep 16, 2025

Omni Boston Hotel at the Seaport
citizenM Boston North Station

citizenM Boston North Station

4 out of 5
80-120 Causeway Street, Boston, MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $220 total per night from Sep 21 to Sep 22
$220 total
Sep 21 - Sep 22
Total with taxes and fees
9.2/10 Wonderful! (3,782 reviews)
Personal experience at citizen M
"Great experience BUT no cups in room, no place to relax except to lie in bed, only one small bench to place suitcase then non place to sit.. pillows too hard"

Reviewed on Sep 16, 2025

citizenM Boston North Station
See all 3,809 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.

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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 $496 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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