Great Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.2/10 Wonderful! (1,002 reviews)
Great location, exceptionally welcoming staff.

Reviewed on Aug. 11, 2025

Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
per person
Oct 28 - Nov 1
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.6/10 Excellent! (1,004 reviews)
Nice quiet place to stay

Reviewed on Aug. 2, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
This hotel is centrally located with many dining options in the Old Port area. It also has a nice rooftop bar with nice views. The room was spacious and very pleasant, everything was clean and well taken care of. Great place to stay in Portland!

Reviewed on Aug. 10, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great option in Old Port. Very convenient to dining, shopping and boat tours. You can walk to everything. Courtyard was lovely in the evening for cocktails around the firepit. Would definitely recommend!

Reviewed on Aug. 7, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Sep 28 - Sep 30
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (1,368 reviews)
This hotel is in the heart of everything! Fast and easy check in. Clean, hot water, the sink was a little clogged but that doesn’t stop anything. Would stay here again.

Reviewed on Aug. 8, 2025

Ready to book your vacation to Great Island?

 

Choose your dates

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 $160 per night from Aug 24 to Aug 25
CA $160
CA $174 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,142 reviews)
"Bed was comfort. Good choice for delivery"

Reviewed on Aug. 9, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $134 per night from Aug 24 to Aug 25
CA $134
CA $146 total
Aug 24 - Aug 25
includes taxes & fees
7.4/10 Good! (132 reviews)
"Everything from Germaine Inn South Portland is pretty good rooms, facilities, pool etc.. I only whish they provide breakfast until 10AM instead of 9AM."

Reviewed on Aug. 11, 2025

Germaine Inn South 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 $178 per night from Sep 1 to Sep 2
CA $178
CA $197 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,039 reviews)
"."

Reviewed on Aug. 9, 2025

Ramada Plaza by Wyndham Portland
See all 2,123 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

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 $662. 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.