Winthrop Vacation Packages 2026 from $653

Winthrop flight + hotel vacation packages

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

The Cape Club Resort

Save 100% on your flight

$653

per person

Oct 26 - Oct 31

found 14 hours ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

A golf course and a restaurant are featured at this hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking. Express check-out, luggage storage, and wedding services are also on offer.

Boston Lodge and Suites

Dorchester

$653

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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

$1,080

per person

Nov 25 - Nov 28

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,393

per person

Nov 25 - Nov 28

found 2 hours ago

Roundtrip flight included

Dallas (DAL) 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.

Raffles Boston

Back Bay

Save 100% on your flight

$1,035

per person

Nov 11 - Nov 14

found 20 hours ago

Roundtrip flight included

Dallas (DAL) 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.

Top Winthrop hotels deals

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$352 nightly

$410 total

Sep 20 - Sep 21

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

$299 nightly

$347 total

Sep 20 - Sep 21

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

$159 nightly

$185 total

Sep 20 - Sep 21

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

The Midtown Hotel MOD Collection by Sonesta

220 Huntington Avenue Boston MA

Free Cancellation

Reserve now, pay when you stay

$203 nightly

$237 total

Sep 20 - Sep 21

Total with taxes and fees

A gym is featured at this hotel, along with self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. There's a fireplace in the lobby and multilingual staff can provide around-the-clock assistance.

Breakfast included

Pet friendly

The Dagny Boston

89 Broad Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$356 nightly

$415 total

Sep 19 - Sep 20

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 communal living room, and a library are also on offer.

Pet friendly

Free WiFi

Hilton Boston Park Plaza

50 Park Plaza Boston MA

Free Cancellation

Reserve now, pay when you stay

$284 nightly

$331 total

Sep 20 - Sep 21

Total with taxes and fees

This luxury hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a 24-hour business center, and a coffee shop are also offered.

Pet friendly

Free WiFi

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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 $653, 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.