Hermit Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Hermit Island Vacation Deals

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

Dormir

CA $796
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,005 reviews)
Great location if you're looking to experience the lake. Staff was very helpful.

Reviewed on Aug 6, 2026

Evalina Hotel

Evalina Hotel

Downtown Portland
CA $2,854
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
10/10 Exceptional! (7 reviews)
Evalina was more than we expected. Super clean and has every convenience item imaginable. The beds were super comfortable. The communication was spectacular which made everything from check in to checkout s smooth. We will definitely be back and hopefully for a longer stay next time.

Reviewed on Aug 4, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

West End
CA $2,607
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (189 reviews)
This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back

Reviewed on Jul 25, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

Downtown Portland
CA $2,023
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,720 reviews)
River View Resort

River View Resort

CA $1,334
per person
Sep 6 - Sep 12
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (331 reviews)
The room was clean (but a bit dated), and comfortable. Staff was welcoming and very friendly. It was perfect to stay w/ my mother and teen-aged son. It was nice to have a full kitchen, and conveniently supplied with the essentials. We would stay there again!

Reviewed on Aug 4, 2026

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Hermit Island Hotel Deals

Flagship Inn and Suites

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME
CA $156
CA $224 total
Sep 2 - Sep 3
includes taxes & fees
8/10 Very good! (1,009 reviews)
"The room was very clean, the staff was kind and helpful we had to ask for help with our TV. They were quick getting us all set. The breakfast is very good. Will be staying there again."

Reviewed on Aug 5, 2026

Flagship Inn and Suites
The Freeport Hotel, an Ascend Collection Hotel

The Freeport Hotel, an Ascend Collection Hotel

506 Us Route 1 Freeport ME
Fully refundable
CA $138
CA $150 total
Aug 30 - Aug 31
includes taxes & fees
The Freeport Hotel, an Ascend Collection Hotel
Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG

450 U.S. Route 1 Freeport ME
Fully refundable
CA $196
CA $214 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Room was clean, great staff, great breakfast and great parking"

Reviewed on Aug 5, 2026

Holiday Inn Express Hotel & Suites Freeport by IHG
See all 1,551 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.

Frequently asked questions

How much does a Hermit Island vacation package cost?
We make it easy for everyone to travel, with Hermit Island vacation packages starting from as low as CA $796. You'll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate escape, why not add some tours and experiences to your travel itinerary?
How do I get a cheap travel package to Hermit Island?
Bundling your flight and hotel with Expedia won't just save you time — it'll save you a nice amount too. A Hermit Island vacation package makes it a breeze to arrange your ideal trip. With more than 550 airlines across the world to pick from, finding convenient flights that suit your schedule won't be a problem. On top of that, we've got over 1,000,000 hotel options globally to select from. Now that's what you call choice. No matter who you are, Expedia can show you the world.
How far in advance should I book my Hermit Island vacation?
You'll be rewarded with the biggest variety at the cheapest prices by booking your vacation to Hermit Island nice and early. Air carriers usually release flights anywhere up to a year before departure, so reserve your spot as soon as possible. Having said that, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream vacation!
What does an Expedia Hermit Island travel package include?
That depends on what kind of escape you're contemplating. Hermit Island vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits your budget and style. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking a Hermit Island travel package?
When you book your flights, hotels and car rentals together, you'll land awesome discounts. Whether you're organizing a wilderness getaway in a cabin or want to stay in a cozy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a Hermit Island Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply select your preferred air carrier and create the perfect Hermit Island trip.
If I'm not able to travel, can I cancel my Hermit Island vacation package?
Certainly, and we're here to help. You may be able to cancel or change your Hermit Island vacation package for free if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If life throws you a curveball, look up our Customer Service Portal for further information.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.