Great Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Docent's Collection at 121 Middle Street
Downtown Portland
CA $2,626
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Great shower. You have to call for more towels and such. No daily house keeper check-ins. But for the space and location. Awesome.
Reviewed on Sep 11, 2026
Ready to book your vacation to Great Island?
Great Island Hotel Deals
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
CA $159
CA $176 total
Sep 20 - Sep 21
includes taxes & fees
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $125
CA $136 total
Sep 14 - Sep 15
includes taxes & fees
6.4/10 (1,121 reviews)
"7 sleepless nights caused by heavy footsteps from unit directly above 108. The floors were filthy. Our feet are black. The room was never cleaned and we had to ask for towels and toiletries etc. Disappointed."
Reviewed on Sep 11, 2026
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.
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.
Land's End Gift Shop
10.0/10 (1 review)
Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.
beach near Merritt House Road
Why not spend a lazy afternoon at beach near Merritt House Road during your trip to Orrs Island? Discover the mountain views while you're in the area.
Cobwork Bridge
10.0/10 (1 review)
You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.
beach near Harpswell Harbor
Why not spend a lazy afternoon at beach near Harpswell Harbor during your trip to Harpswell? Discover the area's sunsets and mountain views.
beach near Bailey Island
Why not spend a lazy afternoon at beach near Bailey Island during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
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 $719. 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.
Explore a world of travel with Expedia
- Motels in Scarborough
- Lodges in Harpswell Center
- Cozy Maine Cottage
- Cottages in Freeport
- Harpswell Hotels
- Cabin Rentals in Hermit Island
- Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
- Oceanfront Hotels in Portland
- Orrs Island Hotels
- Brunswick Hotels
- Popham Beach Direct Oceanfront Cottage Steps to the sand
- Hotels near Popham Beach State Park
- Farmstay in Phippsburg
- Cabin Rentals in Freeport
- Freeport Hotels
- Rv Parks in Bailey Island
- Holiday Inn Express Hotel & Suites Freeport by IHG
- Pet-Friendly Hotels in Brunswick
- Comfort Inn Brunswick
- Hostels in Sebasco Estates
- The Brunswick Hotel
- Little Harbor
- Phippsburg Hotels
- Hotels near LL Bean Flagship Store
- Econo Lodge Freeport
- The Harraseeket Inn & Event House Freeport Downtown
- Cheap Hotels in Portland
- The Beach Pea 2 BR/1 BA Beachside bungalow feet from the Maine shore.
- Portland Hotels
- Travelers Inn
- Beach Hotel Hotels in Old Orchard Beach
- Bay
- Sebasco Harbor Resort & Golf Club
- Pet-Friendly Hotels in Freeport
- Hampton Inn Freeport/Brunswick
- Sea Rose Cottage
- Villas in Harpswell
- Old Orchard Beach Hotels
- Vacation Homes in Bustins Island
- B&B in Freeport
- Moonlight Inn
- Casco Bay Inn
- Hilton Garden Inn Freeport Downtown
- Betty's Place
- South Portland Hotels
- The Beach House Bailey Island Maine
- Relax Inn
- Flights from Toronto (YYZ) to Portland (PWM)
- Flights from Montreal (YUL) to Portland (PWM)
- Flights to Harpswell
- Flights from Ottawa (YOW) to Portland (PWM)
- Flights from Portland Intl. Jetport
- Flights to Portland
- Flights from Halifax (YHZ) to Portland (PWM)
- Flights from Calgary (YYC) to Portland (PWM)
- Flights from Vancouver (YVR) to Portland (PWM)
- East End Beach
- Portland Head Light
- Old Orchard Beach Vacations
- Poland Vacations
- Desert of Maine
- Visit Old Port
- Durham Vacations
- Bailey Island Vacations
- Scarborough Beach State Park
- Ll Bean Flagship Store
- Westbrook Vacations
- Visit Phippsburg
- Pemaquid Point Lighthouse Park
- Ocean Park Vacations
- Portland Museum of Art
- Visit Old Orchard Beach
- South Portland Vacations
- Maine Mall
- Scarborough Vacations
- Windham Vacations
- Visit Hermit Island
- Visit Orrs Island
- Visit Bailey Island
- Palace Playland
- Visit Freeport
- Fort Edgecomb State Historical Site
- Freeport Vacations
- Aquaboggan Water Park
- Higgins Beach
- Lewiston Vacations
- Casco Vacations
- Popham Beach State Park
- Ogunquit Beach
- Portland Vacations
- Coastal Maine Botanical Gardens
- Visit Sebascodegan Island
- Old Orchard Beach Pier
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
