Casco Bay Islands Vacation Packages

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  • Better together

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

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Top Casco Bay Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was CA $1,228, price is now CA $1,163 per person
CA $1,163
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (763 reviews)

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $1,683, price is now CA $1,459 per person
CA $1,459
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (199 reviews)

The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $1,577, price is now CA $1,431 per person
CA $1,431
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (81 reviews)
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.

Reviewed on Oct 27, 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 $1,479, price is now CA $1,377 per person
CA $1,377
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $1,565, price is now CA $1,460 per person
CA $1,460
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)

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Casco Bay Islands Hotel Deals

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 8 to Nov 9
CA $113
CA $125 total
Nov 8 - Nov 9
includes taxes & fees
Clarion Hotel Portland Airport ME
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Fully refundable
The price is CA $90 per night from Nov 3 to Nov 4
CA $90
CA $98 total
Nov 3 - Nov 4
includes taxes & fees
Quality Inn & Suites South Portland
See all 3,419 properties in Casco Bay Islands
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
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Stay near popular Casco Bay Islands attractions

Mackworth Island State Park

Commune with nature and explore the great outdoors at Mackworth Island State Park during your travels in Falmouth. Experience the area's great live music and entertainment choices.
See properties

Frequently asked questions

How much does a Casco Bay Islands vacation package cost?
Starting from a low CA $1,163, a vacation package is your gateway to cheaper travel. Custom make your Casco Bay Islands escape by picking from our comprehensive range of hotels, airfares and rental cars.
How do I get a cheap travel package to Casco Bay Islands?
Just imagine all the fabulous things you could do in Casco Bay Islands with extra cash in your wallet. Watch your savings stack up when you combine your flights and hotel into a Casco Bay Islands vacation package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can select from over 550 airlines and 1,000,000 hotels throughout the world. Whether you're taking off with the family or flying solo, planning a getaway to Casco Bay Islands is better with a package.
How far in advance should I book my Casco Bay Islands vacation?
While not all airlines release ticket prices early, you can usually start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic bargains. If you're booking late, you may still be in luck. Sometimes the cheapest prices emerge just weeks prior to departure.
What does an Expedia Casco Bay Islands travel package include?
Hotels, flights and rental cars — you'll find them all here. With Expedia, you can shape your Casco Bay Islands travel package the way you want. All you have to do is determine what you need. Once you've made your booking, you can add on extras like activities and experiences. The more you bundle, the greater the savings!
What should I know before booking a Casco Bay Islands travel package?
When you book your hotels, flights and car rentals together, you'll be rewarded with incredible discounts. Whether you're organizing a beach break in a villa or want to stay in a comfortable hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Casco Bay Islands Expedia vacation package?
Yes, definitely. Expedia has more than 550 partner airlines to select from around the globe. With all that choice at your fingertips, finding the perfect carrier to whisk you off to Casco Bay Islands shouldn't be hard.
If I'm not able to travel, can I cancel my Casco Bay Islands vacation package?
Yes you can, and we're here to help. You may be able to cancel or amend your Casco Bay Islands vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your travel plans unexpectedly change, browse our Customer Service Portal for more information.

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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.