Hermit Island Vacation Packages

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Top Hermit Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,547, price is now CA $1,346 per person
CA $1,346
per person
May 15 - May 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
We could have moved right in and been happy for life. Flawless.

Reviewed on Mar 30, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,026, price is now CA $1,788 per person
CA $1,788
per person
May 15 - May 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 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 $1,721, price is now CA $1,541 per person
CA $1,541
per person
May 15 - May 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
So spacious, decor is modern yet warm. Staff super friendly and helpful. Perfect location for concerts at Merrill, short walk.

Reviewed on Mar 28, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $1,502, price is now CA $1,377 per person
CA $1,377
per person
May 15 - May 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,599 reviews)
Very nice hotel, located in the center of Portland. Will stay there again.

Reviewed on Apr 1, 2026

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was CA $1,455, price is now CA $1,351 per person
CA $1,351
per person
May 15 - May 18
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (686 reviews)
Historic, cozy, and charming mansions and rooms...our stay was amazing.

Reviewed on Mar 15, 2026

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Hermit Island Hotel Deals

SpringHill Suites by Marriott Freeport Brunswick

SpringHill Suites by Marriott Freeport Brunswick

2 out of 5
500 US-1 Freeport ME
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Apr 15 to Apr 16
CA $136
CA $149 total
Apr 15 - Apr 16
includes taxes & fees
8.8/10 Excellent! (230 reviews)
Booked two queen bed only to end up with a queen and a pull out couch. I was told when I pointed this out that “ sometimes to booking sights don’t specify. Pull out couch is considered a second twin”. I was really disappointed but I did let it go. If anyone cares to follow up, I can give you the ...

Reviewed on Mar 29, 2026

SpringHill Suites by Marriott Freeport Brunswick
Fairfield Inn & Suites by Marriott Brunswick Freeport

Fairfield Inn & Suites by Marriott Brunswick Freeport

3 out of 5
36 Old Portland Rd Brunswick ME
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Apr 26 to Apr 27
CA $153
CA $167 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (457 reviews)
Great

Reviewed on Mar 31, 2026

Fairfield Inn & Suites by Marriott Brunswick Freeport
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

2.5 out of 5
450 U.S. Route 1 Freeport ME
Fully refundable
The price is CA $117 per night from Apr 12 to Apr 13
CA $117
CA $127 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Good breakfast. Friendly staff. Comfy beds!

Reviewed on Mar 31, 2026

Holiday Inn Express Hotel & Suites Freeport by IHG
See all 1,379 properties in Hermit Island
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 Hermit Island due to COVID-19?
In these times of uncertainty, many carriers are offering greater flexibility. Go to our Customer Service Portal for important information about canceling or changing your booking due to COVID-19.
What's the best way to find cheap flights to Hermit Island that have flexible change policies?
Search for your affordable flights to Hermit Island, then mark the "No change fee" box underneath the "Flexible change policies" filter. From then on it's smooth sailing. We appreciate that plans change and flexibility is important, so book with confidence with Expedia.
What are some of the general tips for travelers to Hermit Island during the COVID-19 outbreak?
If it's your first time traveling during COVID-19, you'll notice a few more rules and standards in place. Take note of these tips and make your journey to Hermit Island a smooth one:
  • Look into what, if any, rules or restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book.
  • You must wear a face mask at the airport, even at screening checkpoints. Be prepared to lower your mask for ID purposes when asked by a TSA employee.
  • To reduce the potential of cross-contamination, position your boarding pass on the reader yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA agent.
  • One liquid hand sanitizer container is now permitted in your carry-on baggage. It must be no larger than 12 oz (350 ml), and you'll have to take it out of your bag for X-ray scanning.
  • Empty your personal items from your pocket, such as your keys, phone and wallet, and place them in your carry-on rather than into bins. This will minimize handling during screening.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA employee will need to open your bag for inspection.

Which airlines fly to Hermit Island?
Organize your fare with Southwest Airlines and then begin working on your Hermit Island to-do list. This well-known airline offers 182 flights every month to Portland Intl. Jetport Airport (PWM), a central gateway.
How can I find cheap tickets to Hermit Island?
A great strategy for getting your hands on cheap fares is to be flexible with your travel dates. Start by searching for your flight to Hermit Island, then click on the "flexible dates" box to compare prices for nearby days. Another helpful hint? Book ahead of time. To give you an idea of costs, was the best price for a flight to Hermit Island in the last seven days.
How much is a flight to Hermit Island?
The price of a round-trip airfare to Hermit Island in the last seven days fluctuated between and . If you were journeying one way out of (), you could have gotten a deal from just .
What are the most popular airports to fly into in Hermit Island?
Portland Intl. Jetport Airport (PWM) is the main entry point for those headed to Hermit Island. Approximately 1571 flights every month land at this airport.
When is the cheapest time to fly to Hermit Island?
If you're not set on what date you travel to Hermit Island, leave early in the week. The cheapest day to take off is usually Tuesday, followed closely by Monday. Saturday is typically the priciest day, with many vacationers opting to take off on the weekend.
How much is a plane ticket to Hermit Island?
In the last seven days, tickets to Hermit Island fluctuated between and . Prices tend to rise over time, so land yourself a great deal today.
Which airlines with flights to Hermit Island employ COVID-19 cleanliness policies?
Physical distancing is just the start of new travel measures to minimize the spread of COVID-19. From the check-in desk to arrival, these carriers will bring you to your destination with comfort and confidence:
  • 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.