Great Island Vacation Packages

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Top Great Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
HomeAwhile

HomeAwhile

4 out of 5
Price was CA $1,148, price is now CA $948 per person
CA $948
per person
May 22 - May 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (12 reviews)
It was a perfect stay!

Reviewed on Apr 8, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,931, price is now CA $1,399 per person
CA $1,399
per person
May 22 - May 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
I would definitely recommend the Portland Harbor Hotel. The location was perfect for visiting the Old Port area; one block up from the waterfront. The hotel was quiet. The rooms were well appointed (we had a courtyard view junior suite. The staff was very friendly and a pleasure to speak with. The restaurant had a very nice breakfast menu as well as a dinner menu.

Reviewed on Apr 10, 2026

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $2,042, price is now CA $1,637 per person
CA $1,637
per person
May 22 - May 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Breakfast menu needs more fruits and yogurt-a few healthy options! Hotel was great as was the staff!

Reviewed on Apr 10, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,425, price is now CA $1,144 per person
CA $1,144
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,805, price is now CA $1,481 per person
CA $1,481
per person
May 22 - May 27
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,619 reviews)
We loved our stay here. Location is perfect! Front desk and valet are helpful and make scheduling a shuttle to the airport or train station a breeze. Zero complaints about the property and will be happy to stay here again anytime.

Reviewed on Apr 8, 2026

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Great Island Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Apr 26 to Apr 27
CA $192
CA $213 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
I chose this hotel specifically because it was advertised as pet-friendly, as I was traveling with my well-trained dog. While the location was convenient and the room itself was comfortable, the experience was soured by the lack of transparency regarding the pet policy. When I booked, the additional ...

Reviewed on Apr 6, 2026

The Westin Portland Harborview
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $156 per night from Apr 14 to Apr 15
CA $156
CA $211 total
Apr 14 - Apr 15
includes taxes & fees
9.4/10 Exceptional! (1,189 reviews)
Clean, quiet, good stay.

Reviewed on Apr 6, 2026

Cambria Hotel Portland Downtown-Old Port
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 $168 per night from Apr 26 to Apr 27
CA $168
CA $239 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,767 reviews)
Wonderful staff!

Reviewed on Apr 10, 2026

Portland Harbor Hotel
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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.