Cheap Flight Deals to Gloucester MA from CA $149

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How to find cheap flights to Gloucester?

The cheapest prices found with in the last 7 days for return flights were CA $239 and CA $149 for one-way flights to Gloucester for the period specified. Prices and availability are subject to change. Additional terms apply

Sun., May 18 - Mon., May 26
YXX
Abbotsford Intl.
BOS
Logan Intl.
CA $270 Roundtrip, found 1 hour ago
CA $270
Roundtrip
found 1 hour ago
Select WestJet flight, departing Sun., May 18 from Abbotsford Intl. to Logan Intl., returning Mon., May 26, priced at CA $270 found 1 hour ago
OriginDestinationTravel datesFlights from*
LAXBostonMay 5 to May 6CA $239
PDXBostonMay 30 to June 4CA $309
PVGBostonApril 29 to April 30CA $1,621
HKGBostonJune 28 to July 2CA $1,801
PEKBostonMay 9 to May 9CA $3,130
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXBostonApril 13 to April 16CA $412
*Prices include taxes and fees

Your guide to flights to Gloucester, MA

WestJet fly to Gloucester, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Gloucester MA currently costs between CA $239 and CA $3,130. Prices vary, but for the best fares, travel in May when prices are at their lowest.  

Top tips for finding cheap flights to Gloucester  

The cheapest flight for a round trip to Gloucester is currently CA $239. When you search for flights to Gloucester, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Gloucester for nearby days.  The cheapest month to travel to Gloucester is May from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Gloucester 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Gloucester with Travelocity 

We have top deals on plane tickets even for last minute flights to Gloucester, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Gloucester for less. 

Find The Perfect Hotel For After Your Flight

Luxury Hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is CA $269 per night from Apr. 20 to Apr. 21
CA $269
CA $301 total
includes taxes & fees
Apr 20 - Apr 21
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 CA $226 per night from Apr. 10 to Apr. 11
CA $226
CA $253 total
includes taxes & fees
Apr 10 - Apr 11
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
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
The price is CA $205 per night from May 1 to May 2
CA $205
CA $229 total
includes taxes & fees
May 1 - May 2
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! (375 reviews)
"Nice place."

Reviewed on Nov. 8, 2024

Sea Lion Motel and Cottages
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.

Family Friendly Hotels in Gloucester

The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is CA $226 per night from Apr. 10 to Apr. 11
CA $226
CA $253 total
includes taxes & fees
Apr 10 - Apr 11
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
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is CA $180 per night from Apr. 29 to Apr. 30
CA $180
CA $235 total
includes taxes & fees
Apr 29 - Apr 30
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! (671 reviews)
"Great area; wonderful breakfast; friendly staff!! Will definitely go back!"

Reviewed on Jan. 8, 2025

Ocean House Hotel at Bass Rocks
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
The price is CA $359 per night from May 4 to May 5
CA $359
CA $401 total
includes taxes & fees
May 4 - May 5
Stay at this 3-star beach motel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (411 reviews)
"Fantastic service, clean rooms and comfortable beds. The view is amazing! Just a short drive to the train station and excellent seafood. I would stay here again!"

Reviewed on Oct. 25, 2024

Atlantis Oceanfront Inn
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Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is CA $340 per night from Apr. 10 to Apr. 11
CA $340
CA $380 total
includes taxes & fees
Apr 10 - Apr 11
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! (837 reviews)
"Love the fact that it’s located right on the water. Beautiful views everywhere. Always love staying at The Beauport."

Reviewed on Mar. 31, 2025

Beauport Hotel 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.

Best Gloucester Flight and Hotel Packages

Gloucester flight + hotel packages - economy flights

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

The Boston Hotel

2 out of 5
Save 100% on your flight
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
May 14 - May 18
found 2 days ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
The Whitney Hotel

The Whitney Hotel

4 out of 5
per person
May 14 - May 17
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Boston (BOS)
Don't see what you're looking for?
See all available trips from Toronto to Gloucester
View all trips

Need a car after flight to Gloucester?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Gloucester?
All ready to wander the world? Hoping to kick off your adventure in Gloucester? Some of the 20 airlines that fly here include:

  • Delta Air Lines
  • JetBlue Airways
  • American Airlines

What airport is best to fly into Gloucester?
Logan Intl. Airport is approximately 40 kilometers from downtown Gloucester. It’s the only airport in the city, so you don’t have to worry about your cab driver delivering you to the wrong one!
Where to stay in Gloucester
Few things are as enjoyable as sliding into bed after a huge day of seeing the sights. With an impressive 541 properties in Gloucester, you can take your pick of the cushiest of them.Looking for someplace to get some rest in Gloucester? The Beauport Hotel Gloucester and the Julietta House are some of our favorite properties in the area.
Places to visit in Gloucester
0 Seeking some more options? 0 But that’s not all there is. 0
How to get through airport security fast when traveling to Gloucester
Make your flight to Gloucester a little easier by following these clever security tips:

  • Keep your passport and boarding pass in an easily accessible place. They’ll be the first things you’ll be asked for by airport security personnel.
  • Be aware that belts with metal buckles can set off the body scanner’s alarms. If you have one on, you may be told to step back and remove it before continuing.
  • Laptops and other electronic devices must be placed in separate bins to be X-rayed.
  • Toothpaste, lip balm and other toiletry items in cream, liquid or gel form need to be stored in containers no larger than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • Untie your shoelaces as you approach the body scanner. Depending on what sort of shoes you’re wearing, security may tell you to remove them.
  • Pocketknives and corkscrews are prohibited from entering the plane. Stash them away in your checked luggage to avoid leaving them at the airport security checkpoint.

Plane Tickets To Gloucester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Gloucester. Browse through our inventory to explore a wide range of cheap flights to Gloucester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Gloucester as you anxiously await to exit the plane and explore what Gloucester has to offer. Considering all the amazing local food and culture in Gloucester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Gloucester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Gloucester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Gloucester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Gloucester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.