Great Island Holidays from £1,418

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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.
1802 House Bed and Breakfast

1802 House Bed and Breakfast

3.5 out of 5
Price was £1,603, price is now £1,418 per person
£1,418
per person
26 Sept - 30 Sept
found 16 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.8/10 Exceptional! (117 reviews)
Superb location. Easy and beautiful walk to downtown to avoid all the parking hassle there. Staff is out of this world and the breakfast, we want to go back just for that!!!

Reviewed on 29 Jun 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was £2,048, price is now £1,654 per person
£1,654
per person
26 Sept - 30 Sept
found 16 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on 28 Jun 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 £1,636, price is now £1,454 per person
£1,454
per person
26 Sept - 30 Sept
found 16 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.6/10 Exceptional! (345 reviews)
The room was very clean. The kitchen was well stocked with a few minor exceptions, namely no cutting boards (small thing). The location is perfect for exploring Old Town, highly recommend. The only improvement I would request would be some small fans in the rooms as the meager HVAC couldn't really circulate the air and it got a bit stale during the night. Very minor comfort issue. We will definitely consider staying with Docent again.

Reviewed on 9 Jul 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was £1,704, price is now £1,554 per person
£1,554
per person
26 Sept - 30 Sept
found 16 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. She did as much as she could. Just not sure why the hotel couldn’t fix the A/C in the rooms with KNOWN issues.

Reviewed on 8 Jul 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was £1,775, price is now £1,628 per person
£1,628
per person
26 Sept - 30 Sept
found 16 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.

Reviewed on 5 Jul 2026

Great Island Essential Information

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

Top hotels in Great Island

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is £131 per night from 13 Jul to 14 Jul
£131
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (2,195 reviews)
"Overall a fine place to stay but nothing special. Fridge was turned off when we arrived, coffee at breakfast was cold, and parking was a $10 daily charge. The humidity was also so bad the toilet bowl had constant condensation and dripped so much it created a puddle. The bed and pillows were comfortable ..."

Reviewed on 8 Jul 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 £326 per night from 12 Jul to 13 Jul
£326
12 Jul - 13 Jul
includes taxes & fees
9.4/10 Exceptional! (1,779 reviews)
"Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. ..."

Reviewed on 8 Jul 2026

Portland Harbor Hotel
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 £235 per night from 12 Jul to 13 Jul
£235
12 Jul - 13 Jul
includes taxes & fees
9.4/10 Exceptional! (1,258 reviews)
"Pros: The rooms are big and spacious. Clean rooms. Well maintained Good location. Central Part of downtown. Easy access to restaurants. Gym Good size gym . All necessary equipments available. Good weights range. Cons No smart TV, was hoping to relax and watch Netflix or HBO, or HDMI port to connect ..."

Reviewed on 7 Jul 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,258 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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Stay near popular Great Island attractions

Bailey Island Bridge

9.2/10 (10 reviews)
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.
See properties

Frequently asked questions

How much does a Great Island travel package cost?
Explore the best of Great Island from just £1,418. Choose from a wonderful selection of hotels, flights and rental cars to suit every style and budget. You can score even more discounts when you add a couple of tours or experiences to your package.
If I'm not able to travel, can I cancel my Great Island travel package?
Certainly, and we'll help you every step of the way. You may be able to cancel or amend your Great Island travel package at no cost if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances suddenly change, visit our Customer Service Portal for further information.
How do I get a cheap travel package to Great Island?
You'll save piles of cash if you bundle your flights, car rentals and hotels into a Great Island holiday package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 properties throughout the world, so you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal and unlock even bigger bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Great Island holidays?
Expedia has partnered with online lender Klarna to make your next getaway easier on your wallet. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that falls within your budget. Check out these flexible payment options:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that suit all budgets, so you can take that well-earned holiday now.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan from Klarna.

How far in advance should I book my Great Island holiday?
To bag cheap prices, book ASAP. Airlines generally release tickets, along with some of the lowest fares, nearly a year in advance. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway to Great Island, there are always plenty of great bargains to be had on Expedia. Book something in today!
What does an Expedia Great Island travel package include?
With Expedia, you can select any combination of car rentals, flights and hotels to build your ideal Great Island package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more cash you'll save!
What should I know before booking a Great Island travel package?
You can save big by bundling your flights, hotels and rental cars. Once you've made your booking, you can add on day tours or experiences. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Great Island Expedia travel package?
Definitely. Expedia has more than 550 airline partners to choose from around the globe. With so many choices, finding the perfect carrier to fly you to Great Island won't be hard.

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. Flight-inclusive packages are ATOL protected.