Great Island Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Great Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,351, price is now CA $961 per person
CA $961
per person
Aug 7 - Aug 9
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,007 reviews)
Patrick was great and helped us out a lot. He gave us suggestions somewhere to eat.

Reviewed on May 31, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $3,656, price is now CA $2,634 per person
CA $2,634
per person
Aug 4 - Aug 10
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,768 reviews)
The staff, room service and breakfast all great. I will stay again at this property with a exception location.

Reviewed on Jun 1, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was CA $2,655, price is now CA $1,922 per person
CA $1,922
per person
Jul 26 - Jul 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Staff was very helpful. Polite and friendly.

Reviewed on May 20, 2026

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

2 out of 5
Downtown Portland
Price was CA $4,664, price is now CA $3,830 per person
CA $3,830
per person
Aug 4 - Aug 10
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.8/10 Exceptional! (20 reviews)
Beautiful, clean, modern room with modern amenities. Had everything you could need in an apartment even, and was so close to old for, everything was walking distance Staff with beyond friendly, helpful, assisting, and courteous. If I could give 6/5 stars instead I would have

Reviewed on May 29, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,418, price is now CA $2,065 per person
CA $2,065
per person
Jul 26 - Jul 29
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (315 reviews)
Very nice place, very cclean and friendly.

Reviewed on May 30, 2026

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Great Island Hotel Deals

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $362 per night from Jun 15 to Jun 16
CA $362
CA $438 total
Jun 15 - Jun 16
includes taxes & fees
9.4/10 Exceptional! (1,224 reviews)
"Convenient and dog friendly."

Reviewed on May 31, 2026

Cambria Hotel Portland Downtown-Old Port
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $351 per night from Jun 7 to Jun 8
CA $351
CA $388 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (1,668 reviews)
"Always a wonderful stay at the Regency!"

Reviewed on May 31, 2026

Portland Regency Hotel & Spa
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $345 per night from Jun 7 to Jun 8
CA $345
CA $435 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (1,760 reviews)
"The staff, room service and breakfast all great. I will stay again at this property with a exception location."

Reviewed on Jun 1, 2026

Portland Harbor Hotel
See all 2,129 properties in Great Island
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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Frequently asked questions

Can I cancel my flight booking to Great Island due to COVID-19?
Many airlines now offer more flexibility due to COVID-19. Our handy Customer Service Portal will help solve most queries about flight changes or cancellations. It's also worth scanning over the terms and conditions of your preferred carrier — preferably before booking!
What's the best way to find cheap flights to Great Island that have flexible change policies?
It's as easy as counting 1-2-3 with Expedia. Step 1: Enter your travel dates and click the "Search" button. Step 2? Check the "No change fee" box directly below the "Flexible change policies" filter on the left-hand side of your screen. Step 3. Reserve your flexible and cheap fare to Great Island.
What are some of the general tips for travelers to Great Island during the COVID-19 outbreak?
With new COVID-19 safety guidelines in effect, travel looks a lot different these days. Here are a few things to know before you jet off to Great Island:
  • Before you book a flight, find out if any travel restrictions or bans apply — in both your destination and origin. Get up-to-date information by reviewing government websites.
  • Requirements state that you must wear a face mask at the airport, including at security checkpoints. Be prepared to adjust your mask to verify your identity when asked by a TSA officer.
  • To decrease the risk of cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • One liquid hand sanitizer container is now permitted in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for screening.
  • Remove personal items from your pocket, such as your wallet, phone and small change, and put them in your carry-on instead of into bins. This will reduce handling during screening.
  • If you're taking food through security screening, put it in a clear plastic bag and then into a screening bin. This reduces the likelihood that a TSA agent will need to touch your carry-on bag or food container for closer inspection.

Which airlines fly to Great Island?
Southwest Airlines offers flights into or near Great Island, including 182 that fly into Portland Intl. Jetport Airport (PWM) each month. Select your vacation dates and then book your airfare early to get the best deal.
How can I find cheap tickets to Great Island?
To nab a terrific deal to Great Island, book well in advance. Also consider using Expedia's "flexible dates" link above your search results. This will list the cheapest prices for nearby days. In the last seven days, was the best price for a flight to Great Island.
How much is a flight to Great Island?
In the last seven days, round-trip flights to Great Island sold for as little as and reached a maximum of . For one-way trips leaving (), the cheapest seat during this time was .
What are the most popular airports to fly into in Great Island?
Pack your suitcase and fly into Portland Intl. Jetport Airport (PWM), Great Island's primary flight hub. Book a ticket on one of the 1571 flights that land here every month.
When is the cheapest time to fly to Great Island?
Consider leaving early in the week to score a bargain airfare to Great Island. Tuesday is routinely the most cost-effective day to take off, followed by Monday. Saturday typically has the most expensive prices. This is because lots of travelers prefer to begin their vacation on a weekend.
How much is a plane ticket to Great Island?
In the last seven days, fares varied between and . Take a look at our amazing deals to Great Island, pick your favorite and then get packing!
Which airlines with flights to Great Island employ COVID-19 cleanliness policies?
In an effort to minimize contact between travelers and flight crew during the COVID-19 outbreak, airlines have taken physical distancing and other precautionary measures to the skies. They include:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.