Winthrop, MA

Travel Guide

A coastal town with a lighthouse, sandy beach, and residential buildings.
A historic building with a sign reading "Metcalf Square Business District" and "Welcome".
A coastal town with a beach, a pier, and a dense residential area.
A coastal town with a prominent lighthouse, houses, and a calm sea.
An airplane flying over a city skyline at sunset.
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
$219 nightly
The price is $255 total per night from Nov 22 to Nov 23
$255 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Omni Boston Hotel at the Seaport
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
$105 nightly
The price is $122 total per night from Nov 22 to Nov 23
$122 total
Nov 22 - Nov 23
Total with taxes and fees
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,984 reviews)
"Awesome staff, clean rooms, great area of town"

Reviewed on Oct 22, 2026

The Revolution Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
$176 nightly
The price is $204 total per night from Nov 22 to Nov 23
$204 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (5,136 reviews)
"Everything was great at the hotel except for our initial check-in person. She was working on something and didn’t even look up for quite a while and then told us she would be with us in a minute, and we waited even longer. Seemed like she could have stopped & acknowledged us right away. The gentleman ..."

Reviewed on Oct 22, 2026

Seaport Hotel Boston
See all 4,148 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.
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop MA
Stay at this apartment in Winthrop. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Boston Harbor and Faneuil Hall Marketplace ...
9/10 Wonderful! (20 reviews)
"If you are looking for a comfy stay in a cute neighborhood near Boston, this is a nice spot. The town is quiet enough with a nice walk along the shore, believe it's called the Greenway or similar. I ate at a fresh caught seafood place on the bridge that takes either cash or Venmo. The only thing ..."

Reviewed on Oct 19, 2026

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Crescent Suites Hotel

Crescent Suites Hotel

3 out of 5
287 Crescent Street Waltham MA
Book a stay at this business-friendly aparthotel in Waltham. Enjoy a fitness center, a business center, and a garden. Our guests praise the helpful staff and ...
9.6/10 Exceptional! (1,328 reviews)
"A hidden gem with well-appointed rooms, an easy walk to restaurants (and a classic diner that was perfect - from the food to the owner's hospitality!). Glad I booked the stay there, so much better both in terms of price and room ambiance - than the chain hotels. Thanks to Dana for all."

Reviewed on Oct 22, 2026

Crescent Suites Hotel
Premier Suites - Bay Village

Premier Suites - Bay Village

2 out of 5
1-3-5 Cortes Street Boston MA
Stay at this aparthotel in Boston. Enjoy free WiFi and laundry facilities. Popular attractions Copley Square and Boston Common are located nearby.
Premier Suites - Bay Village
See all 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.

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)
Why not spend a lazy afternoon at Winthrop Beach during your trip to Winthrop? Wander the beaches and seaside in this family-friendly area.
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Things to do

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
Museum of Ice Cream Boston Admission Ticket

Museum of Ice Cream Boston Admission Ticket

$44
per adult
80% of travellers recommend
Museum of Ice Cream Boston Admission Ticket
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

$28
per adult
LEGO Discovery Center Boston Admission Ticket
Boston: Freedom Trail History Small Group Walking Tour

Boston: Freedom Trail History Small Group Walking Tour

$40
per adult
100% of travellers recommend
Boston: Freedom Trail History Small Group Walking Tour
See all activities in Winthrop

Frequently asked questions

Is Winthrop worth visiting?
Winthrop is worth visiting for its beautiful coastal attractions like Winthrop Beach and Donovan Beach, offering travelers a chance to relax by the water. The area also provides diverse dining experiences, with local restaurants serving delicious Italian and North American cuisine.
When is the best time to visit Winthrop?
The best time to visit Winthrop is from May through September, when the weather is typically mild and inviting. For fewer crowds and better value, consider the quieter months of December through March, which offer a cooler, more serene experience.
What is Winthrop known for?
Winthrop is known for its coastal attractions, including Winthrop Beach and Donovan Beach, which offer travelers scenic waterfront experiences. The Winthrop Shore Reservation provides more opportunities to enjoy the outdoors, and the area also features a strong Italian food culture.
What is a good itinerary length for Winthrop?
A good itinerary length for Winthrop is one to two days to enjoy its beaches, like Winthrop Beach and Donovan Beach. An extended stay of three to four days lets you explore Winthrop Shore Reservation and savor the local Italian, North American, or European cuisine.
What are the top things to do in and around Winthrop?
In Winthrop, travelers can enjoy its beautiful coastline and natural areas:

  • Visit Winthrop Beach
  • Stroll along Donovan Beach
  • Explore Winthrop Shore Reservation

How do I plan a trip to Winthrop?
To plan your trip to Winthrop, search for places to stay and book flights on Expedia. Consider booking activities like visiting Winthrop Beach, Donovan Beach, or Winthrop Shore Reservation. Remember to pair outdoor plans with indoor backups for weather flexibility. Booking your rental car in advance will help you explore the area easily.
What cuisines can you find in Winthrop?
In Winthrop, you can find New American cuisine, featuring dishes like gourmet burgers, fresh salads, and creative small plates. Travelers also have options for Italian favorites such as pasta and pizza, Mexican dishes like tacos, and Chinese stir-fries. The area also offers cozy coffee shops and pubs.
Can I book a refundable hotel in Winthrop?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Winthrop by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Winthrop with Expedia?
Expedia makes it easier to plan your Winthrop trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Winthrop?
The best choice depends on your travel style. Hotels in Winthrop can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Winthrop trip on Expedia?
Once you've booked your Winthrop trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Winthrop trip?
Expedia offers customer support before, during, and after your Winthrop trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Winthrop?
If it's your first trip to Winthrop, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Winthrop hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Winthrop hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Winthrop

A historic building with "QUINCY MARKET" sign, surrounded by modern buildings and a clock tower.

Boston

A beach at sunset with the sun low on the horizon, a flag, and buildings in the background.

Revere

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