Name: Flagship Inn and Suites
Price range: $166 total
Rating: 8

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The Latest Hermit Island vacation packages

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

The Meadowmere Resort

Save 100% on your flight

$594

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

8.6/10 Excellent! (1,000 reviews)

Wonderful but be prepared to pay for breakfast. They have coffee and a sweet something but nothing healthy or hot unless you pay for it. Great location.

Reviewed on Jul 8, 2026

Cliff House Maine

Bald Head

Save 100% on your flight

$1,165

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (1,002 reviews)

Amazing property everything was perfection

Reviewed on Jul 9, 2026

Inn By The Sea

Save 100% on your flight

$1,911

per person

Sep 18 - Sep 21

found 16 hours ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (323 reviews)

We just love it there. It is our happy place. Beautiful grounds, comfortable, friendly and downy to earth staff. Wonderful place!

Reviewed on Jun 26, 2026

Evalina Hotel

Downtown Portland

Save 100% on your flight

$968

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

10/10 Exceptional! (5 reviews)

It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on Jun 28, 2026

The Weldon Hotel

Downtown Portland

Save 100% on your flight

$798

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.8/10 Exceptional! (101 reviews)

Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.

Reviewed on Jul 5, 2026

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Hermit Island Hotel Deals

Ocean Gate Inn

70 Ocean Gate Rd Southport ME

$267 nightly

$291 total

Jul 12 - Jul 13

Total with taxes and fees

8.6/10 Excellent! (1,006 reviews)

"This is an amazing escape from a busy travel area! Great activities for a family."

Reviewed on Jul 8, 2026

Flagship Inn and Suites

200 Townsend Avenue Boothbay Harbor ME

Fully refundableReserve now, pay when you stay

$152 nightly

$166 total

Jul 20 - Jul 21

Total with taxes and fees

8/10 Very Good! (1,006 reviews)

"The room was decent. This is definitely an older hotel, but our stay was perfectly fine. The price was was excellent compared to the other hotels a bit closer to the harbor. The pool looked very nice, we just didn't have a chance to use it. The free breakfast was really good."

Reviewed on Jul 7, 2026

Travelers Inn

130 Pleasant St Brunswick ME

Fully refundableReserve now, pay when you stay

$112 nightly

$122 total

Jul 15 - Jul 16

Total with taxes and fees

9/10 Wonderful! (1,010 reviews)

"We had a bit if delay checking in due to the card reader not working. However, they let us move in and return later to pay. There was a nice table with two chairs as well as deak, frig, and 2 nightstands. Ample parking. The bug surprise was the breakfast. It was a continental, but there were bagels ..."

Reviewed on Jul 8, 2026

See all 1,555 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.