Great Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Great Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,013, price is now CA $818 per person
CA $818
per person
Oct 16 - Oct 18
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,020 reviews)
Great hotel. beautiful views of the river. The room was clean and very comfortable. This was my second stay and not the last.

Reviewed on Jul 23, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,090, price is now CA $2,287 per person
CA $2,287
per person
Oct 3 - Oct 5
found 21 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was CA $1,328, price is now CA $1,057 per person
CA $1,057
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.2/10 Very good! (602 reviews)
Nice place in need of an update.

Reviewed on Jul 23, 2026

Dormir

Dormir

3 out of 5
Price was CA $1,122, price is now CA $894 per person
CA $894
per person
Sep 25 - Sep 28
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (1,005 reviews)
Very nice place to stay in Maine!

Reviewed on Jul 21, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was CA $2,858, price is now CA $2,288 per person
CA $2,288
per person
Oct 2 - Oct 5
found 21 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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 Jun 28, 2026

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Great Island Hotel Deals

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 CA $213 per night from Jul 26 to Jul 27
CA $213
CA $235 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,016 reviews)
"Parking, location, clean"

Reviewed on Jul 24, 2026

Fireside Inn & Suites Portland
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 CA $238 per night from Aug 23 to Aug 24
CA $238
CA $263 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (2,180 reviews)
"Not as clean as prior reviews claimed. Close to airport w a better price point but not pleasant or clean and the fridge made a ton of noise. Will not go back."

Reviewed on Jul 23, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $214 per night from Aug 23 to Aug 24
CA $214
CA $237 total
Aug 23 - Aug 24
includes taxes & fees
8.2/10 Very good! (1,570 reviews)
"I travel"

Reviewed on Jul 22, 2026

Clarion Hotel Portland Airport ME
See all 2,296 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 when you spend time 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 vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Great Island from just CA $818. 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.

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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.