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.
1802 House Bed and Breakfast

1802 House Bed and Breakfast

3.5 out of 5
Price was CA $1,829, price is now CA $1,469 per person
CA $1,469
per person
Jun 10 - Jun 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (104 reviews)
Great place to stay for a getaway. Breakfast is outstanding, hostess and her husband prepare fresh ingredients with three tasty courses. Rooms are well decorated, clean, bright and comfortable. We stayed there in 2001 and again in 2025. Our favorite in Kennebunk Port.

Reviewed on Oct 28, 2025

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
Downtown Portland
Price was CA $2,301, price is now CA $1,720 per person
CA $1,720
per person
Jul 17 - Jul 20
found 15 hours ago
Roundtrip flight included
Calgary (YYC) to Portland (PWM)
9.4/10 Exceptional! (1,197 reviews)
Always a beautiful stay here, great location, friendly staff and great bartender! I especially love the bathroom set up, great space, lighting and shower!

Reviewed on May 3, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,185, price is now CA $1,685 per person
CA $1,685
per person
Jun 10 - Jun 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,751 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.

Reviewed on Apr 29, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $2,338, price is now CA $1,845 per person
CA $1,845
per person
Jun 10 - Jun 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,090, price is now CA $2,509 per person
CA $2,509
per person
Jun 10 - Jun 14
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (180 reviews)
This was my first trip to Maine for a quick 38 hour trip for a friend's baby shower from Friday afternoon to Sunday morning. Communication was easy as I was able to text the person at the front desk letting them know my ETA. Once I got my rental car and let them know I was close, the host Maggie literally had the door open to greet me. Once showing me to my room, I looked around the pantry to see local snacks and drinks available to grab and go. Maggie went above and beyond by giving me suggestions for restaurants and shops to check out during my stay. She even had some tissue paper on hand when I commented that I'd forgotten some for my gift. The breakfast was delicious, and the entire spread was a unique assortment for a bed and breakfast style set up. When I arrived back on Saturday after the shower, there was a group of ladies making their own perfumes, and it smelled amazing. I guess they host events in the establishment as I chatted with the host of the event who was staying in the Danforth and had come over from Vermont. Every night I got to have a cozy fire in my room, and there was a book with colored pencils available to add my own story in the book along with previous excerpts from people all over the world and what they did during their stay in Portland. It was fantastic details like this that set it apart from other hotels. Checkout was super easy since I had to leave at 4am for my 6am flight, just leaving the key in a designated area. I will definitely be back!

Reviewed on Apr 28, 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
The price is CA $228 per night from May 10 to May 11
CA $228
CA $304 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (1,753 reviews)
Great location

Reviewed on May 2, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is CA $225 per night from May 6 to May 7
CA $225
CA $249 total
May 6 - May 7
includes taxes & fees
9.4/10 Exceptional! (1,636 reviews)
The room was great. No microwave (which would have been helpful)

Reviewed on Apr 30, 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 $214 per night from May 10 to May 11
CA $214
CA $273 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (1,204 reviews)
Always a beautiful stay here, great location, friendly staff and great bartender! I especially love the bathroom set up, great space, lighting and shower!

Reviewed on May 3, 2026

Cambria Hotel Portland Downtown-Old Port
See all 3,247 properties in Casco Bay Islands
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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.