Great Island Holidays from £217

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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.
Casco Bay Inn

Casco Bay Inn

2 out of 5
Price was £265, price is now £217 per person
£217
per person
22 Oct - 25 Oct
found 3 hours ago
Return flight included
New York (NYC) to Portland (PWM)
8.2/10 Very Good! (1,012 reviews)
The bathroom shower was noisy and when put to full shower a lot of water still came from the tub spout. Not having 24hr desk service is uncommon for me. Property is going thru a makeover and looks good.

Reviewed on 21 Aug 2025

White Barn Inn & Spa, Auberge Resorts Collection

White Barn Inn & Spa, Auberge Resorts Collection

5 out of 5
Save 100% on your flight
Price was £2,598, price is now £1,900 per person
£1,900
per person
26 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.4/10 Exceptional! (100 reviews)
Best resort ever! I can't say one bad thing about this place. Loved loved loved the room they gave us! Super huge and spacious! amazing bathroom, all impeccably decorated and a most comfortable bed. the pool area is gorgeous and relaxing. the restaurant totally spectacular. they had Mercedes - like 5 of them of all types, including a Mayback that they just lend out to their guests for 4 hours at a time. They also have bikes and the town is very bicycle friendly. The hotel is perfectly situated between the downtown brimming with restaurants and cafes and the gooches beach that allows dogs during certain hours so our doggie got to swim in the ocean for the very first time in her life. Was brilliant. the whole stay totally memorable. could not recommend this place any more. please go!

Reviewed on 20 Aug 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was £1,534, price is now £1,130 per person
£1,130
per person
26 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.8/10 Exceptional! (68 reviews)
nice building walkable to shopping + dining

Reviewed on 22 Aug 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was £2,710, price is now £2,081 per person
£2,081
per person
26 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on 9 Aug 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was £1,134, price is now £938 per person
£938
per person
26 Oct - 1 Nov
found 1 day ago
Return direct flight included
London (LHR) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Lovely and knowledgeable staff. Welcoming and romantic stay in a foodie and artsy community.

Reviewed on 20 Aug 2025

Great Island Essential Information

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

Top hotels in Great Island

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is £94 per night from 24 Aug to 25 Aug
£94
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,202 reviews)
"We enjoyed our stay. The room was a bit small, especially the bathroom, but comfortable enough for 2 people. I would have liked a chair besides the desk chair but that was really the only thing I was missing. The bed was very comfortable, in fact one of the best hotel mattresses I've slept on. It ..."

Reviewed on 19 Aug 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is £125 per night from 25 Aug to 26 Aug
£125
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"I like the room and accommodations. The front desk person was a bit brief with me though."

Reviewed on 22 Aug 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is £105 per night from 2 Sept to 3 Sept
£105
2 Sept - 3 Sept
includes taxes & fees
7.8/10 Good! (1,043 reviews)
"The hotel was good enough for the time being (felt safe, clean, etc) but was overall just an okay property."

Reviewed on 20 Aug 2025

Ramada Plaza by Wyndham Portland
See all 2,114 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
Family Friendly Holidays
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

How much does a Great Island travel package cost?
Explore the best of Great Island from just £217. 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.

* 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.