Search Cheap Flights to
Winthrop

Name: Encore Boston Harbor
Rating: 9.6

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Winthrop Flights as Low as $102

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

All deals

One way

Roundtrip

Wed, Sep 17 - Wed, Sep 17

MCO

Orlando Intl.

PSM

Portsmouth Intl.

$102

Roundtrip

found 14 hours ago

Wed, Dec 3 - Wed, Dec 10

MCO

Orlando Intl.

PSM

Portsmouth Intl.

$107

Roundtrip

found 1 day ago

Wed, Dec 3 - Wed, Dec 10

MCO

Orlando Intl.

PSM

Portsmouth Intl.

$112

Roundtrip

found 1 day ago

Wed, Jul 23 - Thu, Jul 24

MCO

Orlando Intl.

BOS

Logan Intl.

$115

Roundtrip

found 19 hours ago

Wed, Dec 3 - Wed, Dec 10

MCO

Orlando Intl.

PSM

Portsmouth Intl.

$117

Roundtrip

found 1 day ago

Sat, Jul 12 - Fri, Jul 18

MCO

Orlando Intl.

BOS

Logan Intl.

$121

Roundtrip

found 1 day ago

Sat, Sep 20 - Sat, Sep 20

MCO

Orlando Intl.

PSM

Portsmouth Intl.

$122

Roundtrip

found 1 day ago

Sat, Jul 12 - Fri, Jul 18

MCO

Orlando Intl.

BOS

Logan Intl.

$124

Roundtrip

found 1 day ago

Mon, Jul 14 - Sat, Jul 26

MCO

Orlando Intl.

BOS

Logan Intl.

$126

Roundtrip

found 2 days ago

Fri, Jul 18 - Sat, Jul 26

MCO

Orlando Intl.

BOS

Logan Intl.

$130

Roundtrip

found 19 hours ago

Fri, Jul 11 - Sat, Jul 12

MCO

Orlando Intl.

BOS

Logan Intl.

$131

Roundtrip

found 19 hours ago

Wed, Jul 23 - Thu, Jul 24

SAT

San Antonio Intl.

BOS

Logan Intl.

$166

Roundtrip

found 1 day ago

Tue, Aug 19 - Sat, Aug 23

MSY

Louis Armstrong New Orleans Intl.

BOS

Logan Intl.

$180

Roundtrip

found 1 day ago

Thu, Oct 9 - Mon, Oct 13

MSY

Louis Armstrong New Orleans Intl.

BOS

Logan Intl.

$187

Roundtrip

found 1 day ago

Tue, Nov 4 - Tue, Nov 11

MCO

Orlando Intl.

BOS

Logan Intl.

$197

Roundtrip

found 1 day ago

Tue, Aug 19 - Sat, Aug 23

MSY

Louis Armstrong New Orleans Intl.

BOS

Logan Intl.

$200

Roundtrip

found 1 day ago

Cheap Flights to Winthrop

Fall in love at first flight with your vacation to Winthrop by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winthrop on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winthrop, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winthrop

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winthrop with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BOS airport.

What is the cheapest month to fly to Winthrop?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winthrop are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winthrop?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winthrop.

What airport is best to fly into Winthrop?

When you’re planning your trip to Winthrop, convenience is the name of the game. Luckily, Winthrop Logan Intl. Airport is nearby so you can deplane and get going on checking off everything on your Winthrop must-do list.

How much are flights to Winthrop?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winthrop on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $102, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winthrop?

The trick to saving a stack of cash on your flight to Winthrop? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $102 right now, why wait?

Winthrop Flight Information
Destination airport	Logan Intl.
Destination airport IATA code	BOS
Roundtrip price	$99

Last Minute Hotel Deals in Winthrop

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...

9/10 Wonderful! (3,630 reviews)

"We recently stayed at the Omni and overall had an enjoyable experience. The lobby is absolutely beautiful like spacious, clean, and very well maintained. It gives a great first impression, and the atmosphere feels upscale and welcoming. The staff were consistently friendly and helpful throughout ..."

Reviewed on Jul 1, 2025

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citizenM Boston Back Bay

408 Newbury street, Boston, MA

Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...

9.2/10 Wonderful! (1,337 reviews)

"Love the iPad controls, fun lights, good use of space and very friendly staff"

Reviewed on Jul 1, 2025

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Seaport Hotel Boston

1 Seaport Lane, Boston, MA

Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...

9.6/10 Exceptional! (2,996 reviews)

"Staying at the seaport hotel was a great location. It was within walking distance to shopping and sight seeing. Parking was very convenient and accessible. I highly recommend staying there."

Reviewed on Jun 30, 2025

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Copley Square Hotel, a FOUND Hotel

47 Huntington Ave, Boston, MA

Stay at this 4-star boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the restaurant and the ...

8.4/10 Very Good! (3,725 reviews)

Reviewed on Jun 30, 2025

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citizenM Boston North Station

80-120 Causeway Street, Boston, MA

Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...

9.2/10 Wonderful! (3,489 reviews)

"Fourth time staying here. Like the convenience of taking the train from Maine."

Reviewed on Jul 1, 2025

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Hyatt Regency Boston/Cambridge

575 Memorial Drive, Cambridge, MA

Stay at this 4-star business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour health club, and valet parking (surcharge). Our guests praise the restaurant ...

8.8/10 Excellent! (1,933 reviews)

"Fun place to spend the night in Cambridge 😊"

Reviewed on Jul 2, 2025

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Harborside Inn Of Boston

185 State St, Boston, MA

Stay at this 4-star hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our ...

9/10 Wonderful! (5,260 reviews)

"This property went above and beyond for my birthday stay I will definitely return next time I’m in Boston"

Reviewed on Jul 2, 2025

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Encore Boston Harbor

1 Broadway, Everett, MA

Stay at this 5-star luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...

9.6/10 Exceptional! (3,059 reviews)

"Our family experience was spectacular. Excellent service, perfect and clean rooms. Everything was incredible."

Reviewed on Jul 2, 2025

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See all 3,772 properties in Winthrop

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.

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