Great Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Great Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,463, price is now CA $1,769 per person
CA $1,769
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
Our stay here was awesome! Very clean and gorgeous room.

Reviewed on Mar 16, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $2,747, price is now CA $2,050 per person
CA $2,050
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.8/10 Exceptional! (94 reviews)
Clean and comfortable. The gym was great.

Reviewed on Mar 6, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,130, price is now CA $2,481 per person
CA $2,481
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $2,753, price is now CA $2,221 per person
CA $2,221
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
Loved this hotel! Our room was spacious, clean, and the staff was very responsive and accommodating. We had a plane cancellation so we had to book an additional 1 night stay last minute and that was not an issue. 100% would recommend!

Reviewed on Mar 16, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,174, price is now CA $1,779 per person
CA $1,779
per person
May 26 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
The shuttle to the downtown area is a perk not advertised which is a great option

Reviewed on Mar 16, 2026

Ready to book your vacation to Great Island?

 

Choose your dates

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 $134 per night from Apr 5 to Apr 6
CA $134
CA $148 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Beautiful room, clean shower

Reviewed on Mar 17, 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $105 per night from Mar 24 to Mar 25
CA $105
CA $117 total
Mar 24 - Mar 25
includes taxes & fees
8/10 Very Good! (1,405 reviews)
We stay here every time we come to Portland. Clean room, friendly staff. Shuttle is a nice bonus.

Reviewed on Mar 16, 2026

Clarion Hotel Portland Airport ME
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
The price is CA $107 per night from Mar 22 to Mar 23
CA $107
CA $118 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,475 reviews)
Great breakfast, real plants in the common areas. Free coffee for guests. Nice pool, gym, etc. Hotel employees were friendly and kind.

Reviewed on Mar 17, 2026

Holiday Inn Portland-By the Bay by IHG
See all 2,060 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.

Explore a world of travel with Expedia

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