Great Island Holidays

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Great Island Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Tamworth

Days Inn by Wyndham Tamworth

2.5 out of 5
Price was S$2,293, price is now S$2,197 per person
S$2,197
per person
16 Dec - 21 Dec
found 6 hours ago
Return flight included
Singapore (SIN) to Portland (PWM)
7.2/10 Good! (533 reviews)
The stay was good value for the money.

Reviewed on 11 Oct, 2025

The Windrifter Resort

The Windrifter Resort

2.5 out of 5
Price was S$2,406, price is now S$2,271 per person
S$2,271
per person
16 Dec - 21 Dec
found 6 hours ago
Return flight included
Singapore (SIN) to Portland (PWM)
8.8/10 Excellent! (325 reviews)
Very roomy “suite” like room . Comfortable bed. Friendly staff too.

Reviewed on 11 Oct, 2025

Best Western York Inn

Best Western York Inn

2.5 out of 5
Price was S$2,296, price is now S$2,260 per person
S$2,260
per person
16 Dec - 21 Dec
found 6 hours ago
Return flight included
Singapore (SIN) to Portland (PWM)
8.4/10 Very Good! (1,007 reviews)
Our first night we were given a room upstairs. The air conditioner was so loud, we could not sleep. The next morning we complained, and they gladly moved us to a room on the first floor. That was our only complaint, otherwise, the staff was friendly, breakfast was nice, well stocked, comfortable beds. We stayed an additional night. Plenty to see in the local area.

Reviewed on 12 Oct, 2025

Top hotels in Great Island

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 S$235 per night from 2 Nov to 3 Nov
S$235
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (1,611 reviews)
"The parking was easy and very secure. The attendants were the best! The room was exquisite, and the coffee, tea, pastry, etc bars on each floor were so nice. All seating areas and the restaurant offered everything we could want. Very welcoming and helpful staff."

Reviewed on 12 Oct, 2025

Portland Harbor Hotel
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 28 Oct to 29 Oct
S$155
28 Oct - 29 Oct
includes taxes & fees
7.8/10 Good! (1,016 reviews)
"A renovation would be good."

Reviewed on 7 Oct, 2025

Fireside Inn & Suites Portland
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is S$127 per night from 22 Oct to 23 Oct
S$127
22 Oct - 23 Oct
includes taxes & fees
7.4/10 Good! (316 reviews)
"Super friendly staff, clean, comfortable and conveniently located! The breakfast was especially good and the staff couldn't have been friendlier! I would absolutely go back!"

Reviewed on 13 Oct, 2025

Germaine Inn South Portland
See all 2,095 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.

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 travellers 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 holiday 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 travellers prefer to begin their holiday 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 favourite and then get packing!
Which airlines with flights to Great Island employ COVID-19 cleanliness policies?
In an effort to minimize contact between travellers 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.