Winthrop Vacation Packages 2025 from $385

Winthrop flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

YOTEL Boston

Seaport District

Save 100% on your flight

per person

Aug 30 - Sep 2

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

per person

Jul 25 - Aug 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

Holly Tree Resort

Save 100% on your flight

per person

Aug 8 - Aug 15

just found

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.

Sea Mist Resort

Save 100% on your flight

per person

Jul 10 - Jul 13

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

This aparthotel features an outdoor pool and an indoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.

Sunbird ANNEX Resort

Save 100% on your flight

per person

Aug 16 - Aug 23

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Boston (BOS)

This hotel features an indoor pool and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Winthrop hotels deals

YOTEL Boston

65 Seaport Blvd, Boston, MA

Free Cancellation

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The hotel's 24-hour gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Free WiFi

Restaurant

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free Cancellation

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A full-service spa, 4 restaurants, and an outdoor pool are all featured at this hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.

Pool

Spa

The Dagny Boston

89 Broad Street, Boston, MA

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a library, and a computer station are also on offer.

Pet friendly

Free WiFi

The Langham, Boston

250 Franklin St, Boston, MA

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.

Pool

Pet friendly

The Revolution Hotel

40 Berkeley Street, Boston, MA

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Pet friendly

Free WiFi

The Godfrey Hotel Boston

505 Washington Street, Boston, MA

Free Cancellation

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.

Pet friendly

Restaurant

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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.

Popular places to visit

Fenway Park

4.5/5(2,499 reviews)

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

Harvard University

4.5/5(1,966 reviews)

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

Boston Common

4.5/5(4,786 reviews)

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.

Frequently asked questions

How much are vacation packages to Winthrop?

With vacation packages on offer from as low as $385, it’s not necessary to empty your piggy bank for your visit to Winthrop. Travelocity can help. Combine hotels, flights and experiences into a convenient package and score some impressive discounts. The more you book, the bigger the savings.

How long should my Winthrop vacation be?

Many visitors pack their bags and vacation in Winthrop for an average of 2 nights. That gives you some guidance, but don’t let it limit you. Whether you stay for a couple of days to see the main sights or hang around to uncover hidden treasures, an amazing adventure awaits.

Where can I get the best vacation package deals for Winthrop?

Travelocity can help you find an awesome Winthrop package deal. With 400 airlines and 1,000,000 properties across the world, you’re sure to find the perfect mix.

Why should I purchase my Winthrop vacation bundle with Travelocity?

Whether you’re planning a month-long vacation or a last-minute escape, we have plenty of alluring destinations to choose from at a great price. What’s more, we provide 24/7 customer support, high-quality service and a Price Match Guarantee. Save yourself money and time and lock in your dream vacation today.

Can I save money on my Winthrop car rental if I book it with my hotel or flight?

Bundling your car, flight and hotel into a Winthrop vacation package is a surefire way to score an amazing deal. Plus, having your own set of wheels gives you absolute freedom to make your way to all those famous sights you’re eager to see. Situated 35 mi from Winthrop, Plymouth Rock is one place that should have a place on your itinerary. Put together a driving playlist and make a day trip of it.

Which airport is best for Winthrop?

Logan Intl. Airport (BOS), 2 mi southwest of inner Winthrop, is most likely where you’ll land. Your other options are T.F. Green Airport (PVD) (50 mi away from central Winthrop) and Manchester-Boston Regional Airport (MHT) (45 mi away from central Winthrop).

What is there to do in Winthrop?

You’ll feel a certain magic in the air as you stroll the streets of Winthrop. Winthrop Beach and Donovan Beach are just two renowned sights that make this city so popular, so put them on your must-see list.

Where should I stay when visiting Winthrop?

If you’re searching for someplace comfortable to lay your head, have a look at the The Winthrop Arms Hotel And Restaurant. It’s the top pick for many visitors.