Great Island Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Great Island Vacation Deals

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

USA Inn

2.5 out of 5
Price was CA $726, price is now CA $613 per person
CA $613
per person
Sep 20 - Sep 26
just found
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
7.8/10 Good! (684 reviews)
Reasonable rates and staff aim to please!

Reviewed on Aug. 16, 2025

River View Resort

River View Resort

2.5 out of 5
Price was CA $1,268, price is now CA $880 per person
CA $880
per person
Sep 20 - Sep 26
just found
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.8/10 Excellent! (294 reviews)
It was a basic suite-like motel. Could use an upgrade. Very 70s

Reviewed on Mar. 30, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was CA $1,788, price is now CA $1,328 per person
CA $1,328
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 Aug. 9, 2025

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
Price was CA $1,602, price is now CA $1,206 per person
CA $1,206
per person
Sep 20 - Sep 26
just found
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.8/10 Excellent! (183 reviews)
Diamond Cove is a peaceful and beautiful property. I highly recommend.

Reviewed on Aug. 15, 2025

Meadowmere Resort

Meadowmere Resort

2.5 out of 5
Price was CA $1,485, price is now CA $1,255 per person
CA $1,255
per person
Sep 20 - Sep 26
just found
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PWM)
8.6/10 Excellent! (1,007 reviews)
The property is nicely maintained but some things are old and need to be fixed. Our balcony door was almost impossible to open and close and we weren’t the only ones with this issue. The gentleman at the front desk (possibly a manager), was not very pleasant or friendly.

Reviewed on Aug. 21, 2025

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Great Island Hotel Deals

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 CA $161 per night from Aug 24 to Aug 25
CA $161
CA $176 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,190 reviews)
"Good hotel for transit"

Reviewed on Aug. 18, 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 CA $211 per night from Aug 25 to Aug 26
CA $211
CA $234 total
Aug 25 - Aug 26
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."

Reviewed on Aug. 17, 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 CA $176 per night from Sep 2 to Sep 3
CA $176
CA $194 total
Sep 2 - Sep 3
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 Aug. 20, 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.
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Frequently asked questions

How much does a Great Island vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Great Island from just CA $613. And the more you bundle, the more you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Great Island?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got it all. Pick a combination that suits you and see your savings pile up. Of course, a package deal is never one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 properties globally, which lets you customize your Great Island vacation.
What are the top hotels in Great Island?
For properties in West Harpswell with cozy beds and friendly service, you can't top Cozy Cottage and Lofty Cottage. If you plan to visit Cundys Harbor as well, you'll get a good night's sleep at 1 Room Luxury Ocean Front Studio Cottage or Beaches, Boating, Cool Ocean Breezes.
How far in advance should I book my Great Island vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Most carriers display prices up to 12 months prior to take off. This is typically the cheapest time to book. If circumstances have left you booking late, last-minute deals to Great Island occasionally appear just weeks before departure.
What does an Expedia Great Island travel package include?
Hotels, flights and rental cars — we've got them covered. With Expedia, you can shape your Great Island package the way you like it. All you have to do is figure out just what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the bigger your savings!
What should I know before booking a Great Island travel package?
When you book your flights, hotels and car rentals together, you'll score terrific discounts. Whether you're planning a wilderness getaway in a cabin or prefer to stay in a luxurious city hotel, Expedia can make it happen for less.
Can I choose my airline with a Great Island Expedia vacation package?
Yes, and with over 550 airlines to pick from globally, you've got lots of choice. Take a look at the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Great Island vacation package?
We understand — life can throw you the odd curveball. If you've locked in a Great Island vacation package and need to amend or cancel it, we're here to help. We suggest checking out our Customer Service Portal first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may charge a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.