Winthrop Vacation Packages 2026 from $644

Winthrop flight + hotel vacation packages

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

Good Hotels Boston

South End

Save 100% on your flight

$644

per person

Aug 21 - Aug 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

Express check-in, express check-out, and luggage storage are available at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Laundry facilities and a virtual front desk are also provided.

Nantucket Inn

Save 100% on your flight

$1,566

per person

Aug 12 - Aug 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

Iris Hotel Boston

Coolidge Corner

Save 100% on your flight

$1,501

per person

Sep 23 - Sep 30

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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, free WiFi in public areas, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$992

per person

Aug 21 - Aug 24

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.

The Whitney Hotel

Beacon Hill

Save 100% on your flight

$1,894

per person

Sep 27 - Oct 2

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

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA

$168 nightly

$195 total

Jul 26 - Jul 27

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-in, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Pet friendly

Free WiFi

Seaport Hotel Boston

1 Seaport Lane Boston MA

$219 nightly

$254 total

Jul 26 - Jul 27

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

Aug 2 - Aug 3

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

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$254 nightly

$296 total

Jul 26 - Jul 27

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.

Harborside Inn Of Boston

185 State St Boston MA

$249 nightly

$290 total

Jul 26 - Jul 27

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.

The Langham, Boston

250 Franklin St Boston MA

Free Cancellation

Reserve now, pay when you stay

$455 nightly

$530 total

Jul 31 - Aug 1

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.

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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 $644, 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.