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.
Blind Tiger Portland - Danforth Street.
West End
CA $2,718
per person
Oct 19 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
Perfect location & beautiful stay! Very unique property. Great recommendations & lovely hospitality. We will definitely come back the next time we’re in Portland!
:)
Reviewed on Aug 23, 2026
Ready to book your vacation to Great Island?
Great Island Hotel Deals
Oceanfront Studio w/ Private Dock in Harpswell!
Harpswell ME
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $94
CA $103 total
Sep 27 - Sep 28
includes taxes & fees
7.2/10 Good! (736 reviews)
"pros : good clean like new AC unit blowing fresh cold air, no unpleasant odor at all, the rooms were decently clean due to recent restoration, comfortable toilet with elongated toilet seat, nice modern bathroom lights and furniture cons: filthy bathtub, disgustingly dirty with pubic hair, non working ..."
Reviewed on Aug 28, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $152
CA $168 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very good! (1,635 reviews)
"Good enough for a one night stay over if flying in/out. Shuttle service was superb. Front desk staff was helpful. Not a five star hotel and the conference area was a bit rowdy with a wedding. However, our room was far away and we were not disturbed."
Reviewed on Aug 27, 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.
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.
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.
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 Channel View Lane
Why not spend a lazy afternoon at beach near Channel View Lane during your trip to Bailey Island? Make time to visit the shops and monuments while you're in the area.
beach near Mackerel Cove Lot
Why not spend a lazy afternoon at beach near Mackerel Cove Lot 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 $994. 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
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- Comfort Inn Brunswick
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- Little Harbor
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- Hotels near LL Bean Flagship Store
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- The Harraseeket Inn & Event House Freeport Downtown
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- The Beach Pea 2 BR/1 BA Beachside bungalow feet from the Maine shore.
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- Bay
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- B&B in Freeport
- Moonlight Inn
- Casco Bay Inn
- Hilton Garden Inn Freeport Downtown
- Betty's Place
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- 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.
