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Gloucester

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Gloucester Flights as Low as $70

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

Spirit Airlines
Thu, Feb 20 - Sat, Feb 22
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Feb 20 from Southwest Florida Intl. to Logan Intl., returning Sat, Feb 22, priced at $70 found 2 days ago
Spirit Airlines
Thu, Feb 20 - Sat, Feb 22
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$79 Roundtrip, found 2 days ago
$79
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Feb 20 from Southwest Florida Intl. to Logan Intl., returning Sat, Feb 22, priced at $79 found 2 days ago
Spirit Airlines
Mon, Mar 10 - Tue, Mar 18
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$80 Roundtrip, found 2 days ago
$80
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Mar 10 from Southwest Florida Intl. to Logan Intl., returning Tue, Mar 18, priced at $80 found 2 days ago
Spirit Airlines
Wed, Feb 12 - Wed, Feb 12
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 12 from Southwest Florida Intl. to Logan Intl., returning Wed, Feb 12, priced at $84 found 3 days ago
Spirit Airlines
Wed, Feb 19 - Fri, Feb 21
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, Feb 19 from Southwest Florida Intl. to Logan Intl., returning Fri, Feb 21, priced at $88 found 3 days ago
Spirit Airlines
Tue, Mar 11 - Tue, Mar 18
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$89 Roundtrip, found 2 days ago
$89
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 11 from Southwest Florida Intl. to Logan Intl., returning Tue, Mar 18, priced at $89 found 2 days ago
Spirit Airlines
Thu, Feb 20 - Sat, Feb 22
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Feb 20 from Southwest Florida Intl. to Logan Intl., returning Sat, Feb 22, priced at $91 found 2 days ago
Spirit Airlines
Thu, Feb 20 - Sun, Feb 23
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Feb 20 from Southwest Florida Intl. to Logan Intl., returning Sun, Feb 23, priced at $94 found 1 day ago
Spirit Airlines
Thu, Feb 20 - Sun, Feb 23
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Feb 20 from Southwest Florida Intl. to Logan Intl., returning Sun, Feb 23, priced at $94 found 1 day ago
Spirit Airlines
Thu, Mar 13 - Mon, Mar 17
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$95 Roundtrip, found 2 days ago
$95
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Mar 13 from Southwest Florida Intl. to Logan Intl., returning Mon, Mar 17, priced at $95 found 2 days ago
Spirit Airlines
Tue, Mar 11 - Wed, Mar 19
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 11 from Southwest Florida Intl. to Logan Intl., returning Wed, Mar 19, priced at $98 found 2 days ago
Delta
Wed, Feb 5 - Sat, Feb 8
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Feb 5 from Southwest Florida Intl. to Logan Intl., returning Sat, Feb 8, priced at $137 found 3 days ago
United
Tue, Feb 11 - Tue, Feb 18
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select United flight, departing Tue, Feb 11 from Southwest Florida Intl. to Logan Intl., returning Tue, Feb 18, priced at $161 found 3 days ago
JetBlue Airways
Thu, Mar 13 - Mon, Mar 17
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 13 from Southwest Florida Intl. to Logan Intl., returning Mon, Mar 17, priced at $167 found 2 days ago
American Airlines
Thu, Feb 20 - Sun, Feb 23
RSW
Southwest Florida Intl.
BOS
Logan Intl.
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Feb 20 from Southwest Florida Intl. to Logan Intl., returning Sun, Feb 23, priced at $173 found 1 day ago
Breeze Airways
Thu, Feb 20 - Sun, Feb 23
RSW
Southwest Florida Intl.
PSM
Portsmouth Intl.
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Feb 20 from Southwest Florida Intl. to Portsmouth Intl., returning Sun, Feb 23, priced at $238 found 1 day 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 February, 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 $70, 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 $70 right now, why wait?

Gloucester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$98

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 $214 per night from Jan 23 to Jan 24
$214
includes taxes & fees
Jan 23 - Jan 24
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! (815 reviews)
"Beautiful property, 1st class all the way"

Reviewed on Jan 12, 2025

Beauport Hotel Gloucester
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! (670 reviews)
"Front desk ladies were wonderful!"

Reviewed on Jan 1, 2025

Get rates
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! (361 reviews)
Great place
"Great relaxing place to stay with amazing views. And lovely kind staff."

Reviewed on Nov 19, 2024

Get rates
The Vista
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! (953 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

Get rates
Castle Manor Inn
Ashworth by the Sea
Ashworth by the Sea
3 out of 5
295 Ocean Blvd, Hampton, NH
The price is $111 per night from Jan 29 to Jan 30
$111
includes taxes & fees
Jan 29 - Jan 30
Stay at this 3-star beach hotel in Hampton. Enjoy 3 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...
7.8/10 Good! (1,178 reviews)
"Amazing"

Reviewed on Jan 16, 2025

Ashworth by the Sea
DoubleTree by Hilton Boston North Shore
DoubleTree by Hilton Boston North Shore
4 out of 5
50 Ferncroft Rd, Danvers, MA
The price is $103 per night from Jan 27 to Jan 28
$103
includes taxes & fees
Jan 27 - Jan 28
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! (1,894 reviews)
"My family and i had a great stay. Our son is special needs and they were so accommodating to him, our other child and my husband and I. Thank you so much, it made our stay so much easier! The water park was amazing too!"

Reviewed on Jan 19, 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 $105 per night from Jan 26 to Jan 27
$105
includes taxes & fees
Jan 26 - Jan 27
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! (1,789 reviews)
"It wad great, we couldnt find parking one night but was able to accommodate."

Reviewed on Jan 21, 2025

Comfort Inn & Suites Logan International Airport
Hampton Inn Salem Boston
Hampton Inn Salem Boston
2.5 out of 5
11 DODGE STREET, Salem, MA
The price is $130 per night from Jan 29 to Jan 30
$130
includes taxes & fees
Jan 29 - Jan 30
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, a fitness center, and valet parking (surcharge). Our guests praise the breakfast ...
9.2/10 Wonderful! (1,004 reviews)
"Great Stay!"

Reviewed on Jan 10, 2025

Hampton Inn Salem Boston
See all 1,640 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.