Great Island Vacation Packages

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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 $1,743, price is now CA $1,343 per person
CA $1,343
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Great experience all around. Will definitely visit again if in the area.

Reviewed on May 25, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $2,239, price is now CA $1,672 per person
CA $1,672
per person
Jul 22 - Jul 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Clean room , friendly Staff , Breakfast was great !!

Reviewed on May 13, 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 $2,904, price is now CA $2,282 per person
CA $2,282
per person
Aug 3 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.8/10 Exceptional! (16 reviews)
Awesome location. Very clean and roomy room. Friendly staff. Top notch!

Reviewed on May 28, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,067, price is now CA $1,657 per person
CA $1,657
per person
Aug 3 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (1,768 reviews)
An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow.

Reviewed on May 25, 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 $2,672, price is now CA $2,282 per person
CA $2,282
per person
Aug 3 - Aug 7
found 10 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.6/10 Exceptional! (316 reviews)
The property is great. The amenities are quality- nothing is cheap… kitchen is stocked & utensils are not flimsy- bedding is nice. Some good touches like under mount lighting in the bathroom that comes on as you walk in- the temperature is easy to keep constant (which is rare in units) it’s very walkable and the parking is easy ($60 per night). Lots of good. The unit itself is very nice. My only complaint is that the furniture is stained and filthy… one chair had caked food and hair (a good vacuuming would have helped) the sofa cushions are broken down & uncomfortable) the bar chairs are very gross and the fabric is stained. They have not appeared to have been cleaned at all… it really is a shame… as an interior designer this is a pretty easy fix. I would love to give them a 5 out of 5. This is just blatant and could not br ignored.

Reviewed on May 27, 2026

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Great Island Hotel Deals

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 $274 per night from May 31 to Jun 1
CA $274
CA $355 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,770 reviews)
"Had an amazing 40th birthday celebration here . Everything was amazing from start to finish ! The courtyard King was well worth it and we loved opening up the door for an evening breeze . Central to dinner and shopping . Walked to dinner reservations + the ferry terminal to ferry over to Peaks Island ..."

Reviewed on May 28, 2026

Portland Harbor Hotel
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 $286 per night from May 31 to Jun 1
CA $286
CA $316 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,661 reviews)
"Our room was wonderful! Very spacious and comfortable. The staff were very attentive and helpful. Valet parking went very smoothly; it ran efficiently and the attendants were very thoughtful and helpful. Our only minor disappointments were that the breakfast was not as good as we had expected and ..."

Reviewed on May 28, 2026

Portland Regency Hotel & Spa
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 $248 per night from May 31 to Jun 1
CA $248
CA $312 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,224 reviews)
"Great location. Good breakfast. Parking was fine."

Reviewed on May 28, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,153 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.