Casco Bay Islands Vacation Packages

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Top Casco Bay Islands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
84 Main

84 Main

4 out of 5
Price was CA $1,427, price is now CA $1,256 per person
CA $1,256
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,445, price is now CA $1,295 per person
CA $1,295
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Really nice room. Tub, separate shower, nice linens.

Reviewed on Feb 7, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was CA $1,429, price is now CA $1,285 per person
CA $1,285
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $1,833, price is now CA $1,657 per person
CA $1,657
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Québec (YQB) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $1,714, price is now CA $1,558 per person
CA $1,558
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

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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 $133 per night from Mar 2 to Mar 3
CA $133
CA $147 total
Mar 2 - Mar 3
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The room was clean and comfortable. Thr hotel itself was beautiful

Reviewed on Feb 4, 2026

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 refundableReserve now, pay when you stay
The price is CA $105 per night from Feb 19 to Feb 20
CA $105
CA $117 total
Feb 19 - Feb 20
includes taxes & fees
8/10 Very Good! (1,343 reviews)
Entire staff was top notch.Thanks to Drew mgr and Mathew.Recommend this place highly

Reviewed on Feb 3, 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Feb 11 to Feb 12
CA $147
CA $215 total
Feb 11 - Feb 12
includes taxes & fees
9.2/10 Wonderful! (1,757 reviews)
Really nice room. Tub, separate shower, nice linens.

Reviewed on Feb 7, 2026

Portland Harbor Hotel
See all 3,225 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.
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Frequently asked questions

Can I cancel my flight booking to Casco Bay Islands due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already locked in your flight to Casco Bay Islands, click through to our Customer Service Portal. The information here will help you figure out which COVID-19 policies apply to your booking and offer advice on the next steps.
What's the best way to find cheap flights to Casco Bay Islands that have flexible change policies?
By using our helpful "No change fee" filter, that's how. Just enter your origin, destination and dates, click "Search," then mark the checkbox directly below the "Flexible change policies" heading (top left of your screen). Expedia makes it a cinch to find low-cost, flexible airfares to Casco Bay Islands.
What are some of the general tips for travelers to Casco Bay Islands during the COVID-19 outbreak?
The COVID-19 pandemic has changed how we travel, but it hasn't dampened our eagerness for exploring. Here are a few tips on how to navigate the new challenges of traveling:
  • Find out if any travel restrictions apply to your origin and destination before booking. Also check if there are any conditions you'll need to follow on arrival, such as proof of a negative COVID-19 test.
  • When you go through airport screening, do not remove your face mask. You will be asked to briefly lower it to verify your identity. Those who refuse to wear a mask may face civil penalties and may also be denied boarding.
  • Instead of handing a TSA officer your boarding pass, position it directly on the reader yourself. Then, hold it up for inspection.
  • You can now take one container of hand sanitizer up to 12 oz (350 ml) in your hand luggage. This will need to be removed for screening.
  • Place any personal items (e.g, keys, phone and wallet) in your carry-on instead of a bin to minimize handling during screening.
  • If you're bringing food through the security checkpoint, put it in a clear plastic bag and then into a screening bin. This lessens the likelihood that a TSA officer will need to touch your food container or carry-on bag for closer inspection.

Which airlines fly to Casco Bay Islands?
Arrange your airfare with Southwest Airlines and then start planning your Casco Bay Islands itinerary. This popular airline offers 182 flights each month to Portland Intl. Jetport Airport (PWM), a key gateway.
How can I find cheap tickets to Casco Bay Islands?
In the last seven days, was the lowest price for a flight to Casco Bay Islands. For even bigger savings, book ahead of time and be flexible with your travel dates. Search for your airfare to Casco Bay Islands, then check out prices for similar time frames by clicking on our "flexible dates" link.
How much is a flight to Casco Bay Islands?
If you were journeying one way from (), you could've landed a bargain fare for just in the last seven days. Round-trip journeys to Casco Bay Islands ranged from only to over the same period.
What are the most popular airports to fly into in Casco Bay Islands?
Portland Intl. Jetport Airport (PWM) is the main entryway for those headed to Casco Bay Islands. Approximately 1571 flights per month touch down at this airport.
When is the cheapest time to fly to Casco Bay Islands?
If you can be flexible with what date you travel to Casco Bay Islands, fly out earlier in the week. The cheapest day to take off is usually Tuesday, closely followed by Monday. Saturday is typically the priciest day, with many people choosing to fly on the weekend.
How much is a plane ticket to Casco Bay Islands?
In the last seven days, plane tickets to Casco Bay Islands ranged from to .
Which airlines with flights to Casco Bay Islands employ COVID-19 cleanliness policies?
In response to the continuing pandemic, the majority of airlines have implemented new rules and measures to help travelers take to the skies again. Here are a few examples:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.