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Cheap Flights to Gloucester

Fall in love at first flight with your vacation to Gloucester 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 Gloucester on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Gloucester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Gloucester 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 Gloucester?

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 Gloucester are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Gloucester?

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

What airport is best to fly into Gloucester?

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

How much are flights to Gloucester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Gloucester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , 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 Gloucester?

The trick to saving a stack of cash on your flight to Gloucester? 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  right now, why wait?

Gloucester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$282

Last Minute Hotel Deals in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,000 reviews)
"Very helpful front desk; welcoming and helpful."

Reviewed on Sep 30, 2025

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Castle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (757 reviews)
"Excellent"

Reviewed on Sep 29, 2025

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Ocean House Hotel at Bass Rocks
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
Book a stay at this business-friendly motel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (425 reviews)
"Fantastic staff. Good options for breakfast. Room was clean and the hotel was super convenient for a wedding we attended."

Reviewed on Oct 1, 2025

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Sea Lion Motel and Cottages
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
Stay at this 3.5-star hotel in Gloucester. Enjoy free parking, a marina, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our ...
8.2/10 Very Good! (746 reviews)
"We loved our stay at the Hotel at Cape Ann Marina. It was nice being able to stay in and have dinner and drinks at the restaurant. Beautiful views of the marina. Great selection of a hot breakfast and fresh fruits. Would definitely recommend this hotel."

Reviewed on Oct 3, 2025

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The Hotel at Cape Ann Marina
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (404 reviews)
"Clean, great water view"

Reviewed on Oct 4, 2025

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The Vista
Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd, Gloucester, MA
Stay at this aparthotel in Gloucester. Enjoy free WiFi and free parking. Popular attractions Good Harbor Beach and Cape Ann are located nearby.
9/10 Wonderful! (47 reviews)
"Parking was safe and clearly marked. The kitchen set up was good"

Reviewed on Oct 2, 2025

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Long Beach Suites
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property ...
9.6/10 Exceptional! (885 reviews)
"Very nice!"

Reviewed on Sep 15, 2025

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Beauport Hotel Gloucester
Lakeside Inn

Lakeside Inn

2 out of 5
595 North Ave, Wakefield, MA
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (2,207 reviews)
"The room was nice, but the front desk woman was exceptional--very helpful in getting a 1st floor room for persons in the party with physical challenges."

Reviewed on Oct 3, 2025

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Lakeside Inn
See all 1,755 properties in Gloucester
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.