Winthrop Vacation Packages 2026 from $419

Winthrop flight + hotel vacation packages

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

The Charles Hotel

West Cambridge

Save 100% on your flight

$419

per person

Mar 19 - Mar 21

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, limo/town car service, and a snack bar/deli are also offered.

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$519

per person

Feb 25 - Feb 28

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$688

per person

Apr 2 - Apr 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Raffles Boston

Back Bay

Save 100% on your flight

$1,052

per person

Mar 27 - Mar 31

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$619

per person

Mar 25 - Mar 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.

Top Winthrop hotels deals

Harborside Inn Of Boston

185 State St Boston MA

$119 nightly

$139 total

Jan 12 - Jan 13

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on offer.

Free WiFi

Restaurant

Hilton Boston Back Bay

40 Dalton St Boston MA

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$167 total

Jan 18 - Jan 19

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, express check-in, and express check-out are also offered.

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$191 nightly

$223 total

Jan 25 - Jan 26

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury 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

Hot Tub

Seaport Hotel Boston

1 Seaport Lane Boston MA

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$175 total

Jan 18 - Jan 19

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.

Pool

Pet friendly

The Dagny Boston

89 Broad Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$183 nightly

$213 total

Feb 9 - Feb 10

Total with taxes and fees

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

Reserve now, pay when you stay

$395 nightly

$460 total

Jan 15 - Jan 16

Total with taxes and fees

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

Don't see what you're looking for?

See all available properties in Winthrop

View all properties

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

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

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.

TD Garden

Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area.

Frequently asked questions

How much are vacation packages to Winthrop?

With vacation packages on offer from as low as $419, 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.