Rattlesnake Island Vacations from $533

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The Latest Rattlesnake Island vacation packages

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

Nautical Mile

$533

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Portland (PWM)

8.6/10 Excellent! (25 reviews)

I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

$680

per person

Nov 26 - Nov 29

found 8 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

9.6/10 Exceptional! (400 reviews)

We loved staying at the Docent's Collection at 121 Middle Street. Great staff, great location and great studio. Bed was excellent and the bathroom was large with very nice shower. Loved staying there.

Reviewed on Oct 24, 2026

Inn By The Sea

Save 100% on your flight

$946

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

9.6/10 Exceptional! (342 reviews)

Great pet friendly resort that allowed the dog to remain in the room while dining in the restaurant. Pet was allowed in the lounge area where they offered the same dining room menu, if you wanted to bring you pet along . Pet treats and food and water dishes already in place in the room.

Reviewed on Oct 22, 2026

White Barn Inn & Spa, Auberge Collection

Save 100% on your flight

$1,841

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

9.6/10 Exceptional! (124 reviews)

84 Main

$643

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Portland (PWM)

9.8/10 Exceptional! (58 reviews)

The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.

Reviewed on Jul 17, 2026

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