Winthrop Vacation Packages 2026 from $471

Winthrop flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

$471

per person

Dec 9 - Dec 13

found 5 hours ago

Roundtrip flight included

Orlando (MCO) 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

$889

per person

Jan 14 - Jan 17

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.

Battery Wharf Hotel, Boston Waterfront

North End

$552

per person

Jan 6 - Jan 8

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a sauna on site, and laundry facilities and concierge services are also offered.

Raffles Boston

Back Bay

$1,435

per person

Jan 25 - Jan 29

found 8 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like free WiFi. You'll appreciate the a rooftop terrace, bar/lounge, and concierge services.

Four Seasons Hotel Boston

Bay Village

$1,441

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Top Winthrop hotels deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$191 nightly

$223 total

Nov 22 - Nov 23

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. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Pool

Hot Tub

The Revolution Hotel

40 Berkeley Street Boston MA

$113 nightly

$131 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

Seaport Hotel Boston

1 Seaport Lane Boston MA

Free Cancellation

Reserve now, pay when you stay

$165 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

Encore Boston Harbor

1 Broadway Everett MA

$244 nightly

$273 total

Nov 30 - Dec 1

Total with taxes and fees

This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Free self parking is free for guests, and you can enjoy a meal in one of the 15 restaurants.

Spa

Parking included

Harborside Inn Of Boston

185 State St Boston MA

$129 nightly

$150 total

Nov 22 - Nov 23

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

The Westin Copley Place, Boston, a Marriott Hotel

10 Huntington Ave Boston MA

Free Cancellation

Reserve now, pay when you stay

$207 nightly

$241 total

Nov 22 - Nov 23

Total with taxes and fees

This smoke-free hotel features 5 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

Spa

Pet friendly

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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.

Stay near popular Winthrop attractions

A lighthouse with a red, white, and blue top, a beach, and a town with houses.

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.

See properties

Frequently asked questions

How much are vacation packages to Winthrop?

With vacation packages on offer from as low as $471, 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.