Winthrop Vacation Packages 2026 from $686

Winthrop flight + hotel vacation packages

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

DoubleTree by Hilton Hotel Boston - Westborough

Save 100% on your flight

$686

per person

Jun 24 - Jun 30

found 24 hours ago

Roundtrip flight included

St. Petersburg (PIE) to Boston (BOS)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,369

per person

Jul 23 - Jul 26

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.

Nantucket Inn

$2,022

per person

Jul 22 - Jul 28

found 15 hours ago

Roundtrip non-stop flight included

Denver (DEN) 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, free WiFi in public areas, and free airport shuttle. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

By the Sea Guests Bed & Breakfast & Suites

$1,253

per person

Jul 22 - Jul 28

found 15 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Summer House Hotel

$2,326

per person

Jul 22 - Jul 28

found 15 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Boston (BOS)

This hotel features a private beach and 2 restaurants. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas. Enjoy the seasonal outdoor pool and unwind at the beach bar and poolside bar.

Top Winthrop hotels deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

$261 nightly

$304 total

May 25 - May 26

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.

The Revolution Hotel

40 Berkeley Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$167 total

May 25 - May 26

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.

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$214 nightly

$249 total

May 29 - May 30

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.

The Godfrey Hotel Boston

505 Washington Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$259 nightly

$302 total

May 25 - May 26

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a business center, and a coffee shop are also offered.

Club Quarters Hotel Faneuil Hall, Boston

161 Devonshire St Boston MA

Free Cancellation

Reserve now, pay when you stay

$215 nightly

$251 total

May 25 - May 26

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the in-room fitness and conveniences like a 24-hour front desk and concierge services.

The Midtown Hotel MOD Collection by Sonesta

220 Huntington Avenue Boston MA

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$220 total

May 25 - May 26

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.

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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.

Harvard University

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

Gillette Stadium

Catch an event at Gillette Stadium during your trip to Foxborough. Experience the area's acclaimed theater scene and great live music.

Frequently asked questions

How much are vacation packages to Winthrop?

With vacation packages on offer from as low as $686, 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.