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Gloucester

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Gloucester Flights as Low as $92

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

Spirit Airlines
Wed, May 21 - Tue, May 27
MCO
Orlando Intl.
BOS
Logan Intl.
$92 Roundtrip, found 4 days ago
$92
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, May 21 from Orlando Intl. to Logan Intl., returning Tue, May 27, priced at $92 found 4 days ago
Spirit Airlines
Thu, Jun 5 - Sun, Jun 8
MCO
Orlando Intl.
BOS
Logan Intl.
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Jun 5 from Orlando Intl. to Logan Intl., returning Sun, Jun 8, priced at $100 found 3 days ago
Breeze Airways
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Portsmouth Intl., returning Wed, Aug 13, priced at $102 found 1 day ago
Spirit Airlines
Fri, May 23 - Tue, May 27
MCO
Orlando Intl.
BOS
Logan Intl.
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, May 23 from Orlando Intl. to Logan Intl., returning Tue, May 27, priced at $105 found 4 days ago
Breeze Airways
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Portsmouth Intl., returning Wed, Aug 13, priced at $107 found 1 day ago
Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $108 found 2 days ago
Spirit Airlines
Fri, Jun 13 - Sat, Jun 14
MCO
Orlando Intl.
BOS
Logan Intl.
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Jun 13 from Orlando Intl. to Logan Intl., returning Sat, Jun 14, priced at $110 found 4 days ago
Spirit Airlines
Wed, Jun 4 - Mon, Jun 9
MCO
Orlando Intl.
BOS
Logan Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jun 4 from Orlando Intl. to Logan Intl., returning Mon, Jun 9, priced at $111 found 2 days ago
Spirit Airlines
Thu, Jun 12 - Fri, Jun 13
MCO
Orlando Intl.
BOS
Logan Intl.
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Jun 12 from Orlando Intl. to Logan Intl., returning Fri, Jun 13, priced at $112 found 4 days ago
Spirit Airlines
Wed, Jun 4 - Mon, Jun 9
MCO
Orlando Intl.
BOS
Logan Intl.
$116 Roundtrip, found 2 days ago
$116
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jun 4 from Orlando Intl. to Logan Intl., returning Mon, Jun 9, priced at $116 found 2 days ago
Spirit Airlines
Fri, May 23 - Sat, May 24
MCO
Orlando Intl.
BOS
Logan Intl.
$120 Roundtrip, found 4 days ago
$120
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, May 23 from Orlando Intl. to Logan Intl., returning Sat, May 24, priced at $120 found 4 days ago
Frontier Airlines
Fri, Jul 11 - Mon, Jul 14
MCO
Orlando Intl.
BOS
Logan Intl.
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jul 11 from Orlando Intl. to Logan Intl., returning Mon, Jul 14, priced at $134 found 2 days ago
United
Tue, May 13 - Tue, May 20
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select United flight, departing Tue, May 13 from Orlando Intl. to Logan Intl., returning Tue, May 20, priced at $199 found 1 day ago
American Airlines
Tue, May 13 - Tue, May 20
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 13 from Orlando Intl. to Logan Intl., returning Tue, May 20, priced at $199 found 1 day ago
Delta
Sat, Jul 5 - Sun, Jul 6
MCO
Orlando Intl.
BOS
Logan Intl.
$227 Roundtrip, found 23 hours ago
$227
Roundtrip
found 23 hours ago
Select Delta flight, departing Sat, Jul 5 from Orlando Intl. to Logan Intl., returning Sun, Jul 6, priced at $227 found 23 hours ago
JetBlue Airways
Sun, Jul 13 - Sun, Jul 20
MCO
Orlando Intl.
BOS
Logan Intl.
$227 Roundtrip, found 2 days ago
$227
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Jul 13 from Orlando Intl. to Logan Intl., returning Sun, Jul 20, priced at $227 found 2 days ago

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 May, 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 16 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 $92, 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 $92 right now, why wait?

Gloucester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$91

Last Minute Hotel Deals in Gloucester

Beauport Hotel Gloucester
Beauport Hotel Gloucester
3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is $267 per night from May 6 to May 7
$267
includes taxes & fees
May 6 - May 7
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! (846 reviews)
"I cannot say enough good things about the Beauport, the staff, the accommodations, the amenities all above and beyond. My favorite place in my favorite town."

Reviewed on Apr 30, 2025

Beauport Hotel Gloucester
Ocean House Hotel at Bass Rocks
Ocean House Hotel at Bass Rocks
4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is $194 per night from May 12 to May 13
$194
includes taxes & fees
May 12 - May 13
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! (684 reviews)
"Beautiful location, but ants were in the room at one point -- I hope those get addressed."

Reviewed on Apr 24, 2025

Ocean House Hotel at Bass Rocks
Castle Manor Inn
Castle Manor Inn
2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is $222 per night from May 7 to May 8
$222
includes taxes & fees
May 7 - May 8
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! (954 reviews)
"The Innkeeper and staff were very accommodating. The room was very clean and all we really needed for a few nights. The rooms were updated. We would have liked a table or bench or chair to put items on or sit on. There was not enough room in the bathroom to put toiletries. We would go back."

Reviewed on Dec 2, 2024

Castle Manor Inn
The Vista
The Vista
2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is $196 per night from May 6 to May 7
$196
includes taxes & fees
May 6 - May 7
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! (361 reviews)
Great place
"Great relaxing place to stay with amazing views. And lovely kind staff."

Reviewed on Nov 19, 2024

The Vista
DoubleTree by Hilton Boston North Shore
DoubleTree by Hilton Boston North Shore
4 out of 5
50 Ferncroft Rd, Danvers, MA
The price is $122 per night from May 25 to May 26
$122
includes taxes & fees
May 25 - May 26
Stay at this 4-star golf hotel in Danvers. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (1,997 reviews)
"We had a minor medical emergency & the staff and security were helpful, caring, & professional. Wonderful staff working at the front desk and security positions. Thank you!"

Reviewed on May 1, 2025

DoubleTree by Hilton Boston North Shore
Comfort Inn & Suites Logan International Airport
Comfort Inn & Suites Logan International Airport
2.5 out of 5
85 American Legion Hwy, Revere, MA
The price is $164 per night from May 27 to May 28
$164
includes taxes & fees
May 27 - May 28
Stay at this hotel in Revere. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. ...
9/10 Wonderful! (1,991 reviews)
"It's a comfortable and conveniently located hotel with a lot of amenities, but what stands out for me most is the competency and pleasantness of the staff. They are why I keep choosing this hotel when I am flying into Boston."

Reviewed on Apr 30, 2025

Comfort Inn & Suites Logan International Airport
Best Western Plus North Shore Hotel
Best Western Plus North Shore Hotel
2.5 out of 5
50 Dayton St, Danvers, MA
The price is $146 per night from May 19 to May 20
$146
includes taxes & fees
May 19 - May 20
Book a stay at this business-friendly hotel in Danvers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (1,000 reviews)
"Overall a nice hotel and easy to commute to, just disappointed by the pool, it is not kid friendly for younger children, there was only a small portion that we could utilize as it then dropped off to 5 and then 6 feet deep and had to try and keep our kids from going past the small area that they ..."

Reviewed on Apr 24, 2025

Best Western Plus North Shore Hotel
Lakeside Inn
Lakeside Inn
2 out of 5
595 North Ave, Wakefield, MA
The price is $116 per night from May 8 to May 9
$116
includes taxes & fees
May 8 - May 9
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 ...
7.2/10 Good! (2,152 reviews)
"This property need a elevator."

Reviewed on Apr 30, 2025

Lakeside Inn
See all 1,723 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.