Winthrop Vacation Packages 2025/2026 from $193

Winthrop flight + hotel vacation packages

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

DoubleTree by Hilton Boston North Shore

Save 100% on your flight

$193

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features 2 restaurants, an indoor pool, and a gym. Families will appreciate the arcade/game room and convenience store. Enjoy the sauna and perks like free self parking.

Boston Harbor Hotel

North End

$608

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$552

per person

Jan 8 - Jan 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Cambria Hotel Boston Somerville

Spring Hill

Save 100% on your flight

$372

per person

Dec 10 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Valet parking and a safe deposit box are also offered on site.

citizenM Boston North Station

West End

Save 100% on your flight

$394

per person

Dec 4 - Dec 7

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. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Top Winthrop hotels deals

Seaport Hotel Boston

1 Seaport Lane, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$192 total

Nov 23 - Nov 24

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 Revolution Hotel

40 Berkeley Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$139 total

Nov 23 - Nov 24

Total with taxes and fees

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

citizenM Boston North Station

70 Causeway Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$156 total

Nov 30 - Dec 1

Total with taxes and fees

Free WiFi

Restaurant

The Dagny Boston

89 Broad Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$176 nightly

$205 total

Nov 30 - Dec 1

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

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$212 total

Nov 25 - Nov 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

citizenM Boston Back Bay

408 Newbury street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$162 total

Nov 16 - Nov 17

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

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

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

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.

Harvard University

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

Frequently asked questions

How much are vacation packages to Winthrop?

With vacation packages on offer from as low as $193, 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.