Winthrop Vacation Packages 2025/2026 from $263

Winthrop flight + hotel vacation packages

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

The Wylie Inn and Conference Center at Endicott College

Save 100% on your flight

$263

per person

Jan 8 - Jan 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the conference center and conference space, and free internet in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Boston Lodge and Suites

Dorchester

$447

per person

Jan 7 - Jan 12

found 1 day ago

Roundtrip flight included

Nashville (BNA) 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.

The Inn at Hastings Park, Relais & Chateaux - Boston

$634

per person

Jan 7 - Jan 12

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

A restaurant and a bar/lounge are featured at this hotel. A terrace, limo/town car service, and a snack bar/deli are also on offer.

Lakeside Inn

Save 100% on your flight

$354

per person

Jan 8 - Jan 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Hyatt Regency Boston Harbor

East Boston

Save 100% on your flight

$309

per person

Jan 8 - Jan 13

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. Guests will appreciate perks like free WiFi and a free airport shuttle. Valet parking, a 24-hour business center, and a terrace are also offered.

Top Winthrop hotels deals

citizenM Boston North Station

70 Causeway Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$141 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 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.

Free WiFi

Restaurant

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$212 total

Nov 29 - Nov 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 Revolution Hotel

40 Berkeley Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$97 total

Nov 24 - Nov 25

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.

The Dagny Boston

89 Broad Street Boston MA

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$173 total

Dec 14 - Dec 15

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.

Seaport Hotel Boston

1 Seaport Lane Boston MA

Free Cancellation

Reserve now, pay when you stay

$153 nightly

$178 total

Nov 27 - Nov 28

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.

Harborside Inn Of Boston

185 State St Boston MA

$129 nightly

$150 total

Nov 26 - Nov 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.

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

4.5/5(2,499 reviews)

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

Boston Common

4.5/5(4,786 reviews)

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Harvard University

4.5/5(1,966 reviews)

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 $263, 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.