Rattlesnake Island Vacations from $590

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The Latest Rattlesnake Island vacation packages

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

Portland Harbor Hotel

Downtown Portland

$590

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.2/10 Wonderful! (1,864 reviews)

Just okay, our room had issues, fireplace, noise from the heating or AC, toilet seat broken, PARKING GARAGE TO FAR AWAY, high cost for our room.

Reviewed on Oct 9, 2026

Blind Tiger Portland - Danforth Street.

West End

$813

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip non-stop flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (193 reviews)

Adorable stylish house and spacious room comfortable bed. Worth the walk to old port. Will come back!

Reviewed on Oct 6, 2026

Inn By The Sea

$777

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (333 reviews)

The Docent's Collection at 121 Middle Street

Downtown Portland

$774

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.6/10 Exceptional! (400 reviews)

Portland Regency Hotel & Spa

Downtown Portland

$649

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Portland (PWM)

9.4/10 Exceptional! (1,759 reviews)

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Rattlesnake Island Hotel Deals

Mill Falls Resort Collection at the Lake

281 Daniel Webster Hwy Meredith NH

$199 nightly

$215 total

Nov 2 - Nov 3

Total with taxes and fees

Best Western Plus Landmark Inn

480 Main Street Laconia NH

Fully refundableReserve now, pay when you stay

$101 nightly

$110 total

Nov 1 - Nov 2

Total with taxes and fees

Fireside Inn & Suites Gilford

17 Harris Shore Road Gilford NH

Fully refundableReserve now, pay when you stay

$124 nightly

$135 total

Nov 1 - Nov 2

Total with taxes and fees

9/10 Wonderful! (1,005 reviews)

"The staff was so kind we had the best time in the pool. It was easy Parking. The bed was extremely comfortable and everything was clean."

Reviewed on Oct 10, 2026

See all 1,783 properties in Rattlesnake 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.