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.
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,148, price is now CA $1,080 per person
CA $1,080
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,780 reviews)

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $1,679, price is now CA $1,432 per person
CA $1,432
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)
Very helpful and friendly staff

Reviewed on Oct 28, 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 CA $1,460, price is now CA $1,255 per person
CA $1,255
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $1,348, price is now CA $1,232 per person
CA $1,232
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was CA $1,403, price is now CA $1,304 per person
CA $1,304
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (763 reviews)
Very nice bed and breakfast consisting of multiple distinguished historic residences. Good breakfast with one protein source (e.g., quiche) daily. Our room was nice but relatively small compared to similar accommodations at Bretton Arms and Thorn Hill in New Hampshire. Also, the buildings that were part of the Captain’s Collection were not clearly marked so it wasn’t clear which buildings we could enter. Exceptionally well-appointed common areas in our building but wish that we knew which other buildings were accessible. Easy parking. Five-minute walk to town. Great walkable restaurants are available.

Reviewed on Oct 31, 2026

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Great Island Hotel Deals

Oceanfront Studio w/ Private Dock in Harpswell!

Oceanfront Studio w/ Private Dock in Harpswell!

3 out of 5
Harpswell ME
Get rates
Oceanfront Studio w/ Private Dock in Harpswell!
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 CA $151 per night from Nov 22 to Nov 23
CA $151
CA $167 total
Nov 22 - Nov 23
includes taxes & fees
The Westin Portland Harborview
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 $113 per night from Nov 9 to Nov 10
CA $113
CA $125 total
Nov 9 - Nov 10
includes taxes & fees
Clarion Hotel Portland Airport ME
See all 2,199 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,080. 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.