Great Island Holidays from £823

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Your Great Island Holiday

Book one of our holiday packages to Great Island and uncover everything this destination has to offer, starting with West Harpswell. From its culture to its many other delights, this city is an incredible mix of fun and excitement. A trip to Great Island offers lots of things to see and do. Not sure where to kick off your itinerary? Cundys Harbour is one of the most popular places to stay here. Expedia has everything you need when it comes to planning your Great Island holiday. From flights and hotels, to activities and more, we're here to help you create a travel experience like no other.

Top Great Island Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was £964, price is now £823 per person
£823
per person
16 May - 22 May
found 9 hours ago
Return direct flight included
London (LON) to Portland (PWM)
9/10 Wonderful! (49 reviews)
Quaint bed-and-breakfast. Clean and comfortable. Would definitely stay again.

Reviewed on 8 Dec 2025

And.N Lodging

And.N Lodging

2 out of 5
Price was £1,130, price is now £987 per person
£987
per person
16 May - 22 May
found 9 hours ago
Return direct flight included
London (LON) to Portland (PWM)
No reviews
The Lodge at Pleasant Point

The Lodge at Pleasant Point

2 out of 5
Price was £1,510, price is now £1,331 per person
£1,331
per person
16 May - 22 May
found 9 hours ago
Return direct flight included
London (LON) to Auburn (LEW)
9/10 Wonderful! (2 reviews)
Beautiful peaceful place. Basic, perfectly good accommodations but nothing fancy so don’t book if that’s your thing and leave this treasure to the rest of us 😊

Reviewed on 17 Oct 2025

Mayville Union House

Mayville Union House

3 out of 5
Price was £1,438, price is now £1,284 per person
£1,284
per person
16 May - 22 May
found 9 hours ago
Return direct flight included
London (LON) to Portland (PWM)
No reviews
Dormir

Dormir

3 out of 5
Price was £1,106, price is now £992 per person
£992
per person
16 May - 22 May
found 9 hours ago
Return direct flight included
London (LON) to Portland (PWM)
8.8/10 Excellent! (999 reviews)
Enjoyed my stay. Very reliable.

Reviewed on 20 Mar 2026

Great Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)

Top hotels in Great Island

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 £107 per night from 23 Apr to 24 Apr
£107
23 Apr - 24 Apr
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 6 Apr 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 £111 per night from 21 Apr to 22 Apr
£111
21 Apr - 22 Apr
includes taxes & fees
9.4/10 Exceptional! (1,187 reviews)
Clean, quiet, good stay.

Reviewed on 6 Apr 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 £126 per night from 12 Apr to 13 Apr
£126
12 Apr - 13 Apr
includes taxes & fees
9.2/10 Wonderful! (1,764 reviews)
We have really enjoyed our stay at Portland Harbor Hotel. Our room was clean, the location is super convenient, and the staff was super helpful with recommendations, especially Adam. Everywhere he recommended to check out was amazing! He was also very cheerful and welcoming daily. If we’re ever back ...

Reviewed on 8 Apr 2026

Portland Harbor Hotel
See all 2,098 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
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Family Friendly Holidays

Popular places to visit

Bailey Island Bridge

Find out about the history of Bailey Island with a stop at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.

Bailey Island Bridge

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.

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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. Flight-inclusive packages are ATOL protected.