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.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Price was CA $1,102, price is now CA $973 per person
CA $973
per person
Jun 20 - Jun 23
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (77 reviews)
Charming and easy access to the Golf Course

Reviewed on Sep 21, 2025

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,740, price is now CA $1,420 per person
CA $1,420
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Very well kept… great staff we had a great time

Reviewed on Apr 14, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,584, price is now CA $1,310 per person
CA $1,310
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Very convenient and helpful staff.

Reviewed on May 10, 2026

Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Price was CA $1,416, price is now CA $1,236 per person
CA $1,236
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
7.6/10 Good! (1,049 reviews)
The internet was not secure The room did not have room darkening drapes. Breakfast was good. TV not usefall no NBC,ABC,CBS channel and very few other channels to watch except old out of date programming.

Reviewed on May 11, 2026

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
Price was CA $2,451, price is now CA $2,187 per person
CA $2,187
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
The breakfast on Mother’s Day was amazing. We loved the Luna rooftop. The staff and bartenders were top notch. The hotel was very well kept. Definitely will be back.

Reviewed on May 11, 2026

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Casco Bay Islands Hotel Deals

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 $254 per night from May 25 to May 26
CA $254
CA $333 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,763 reviews)
Best location in Portland. The free bikes were the highlight, We went everywhere with them. Very convenient! The staff was very nice.

Reviewed on May 10, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from May 26 to May 27
CA $225
CA $249 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,648 reviews)
Very nice hotel with a wonderful staff. Also, in a prime location that allowed us to walk to everything we did.

Reviewed on May 11, 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $229 per night from May 26 to May 27
CA $229
CA $291 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,214 reviews)
Very clean and modern design, spacious room and overall the place was very quiet and made for a good night's sleep. Convenient to have the garage attached to the hotel, you just have to have your ticket validated by the front desk, but allows you to come and go as you please for the parking fee.

Reviewed on May 12, 2026

Cambria Hotel Portland Downtown-Old Port
See all 3,348 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.