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New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Portland Holiday Packages

Amazing!!!!!
Someday I may just live in one of those houses.  Maybe when I get my doctorate I can teach at Th
Portland Holiday Packages
Want to book a holiday to Portland? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Portland holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Portland on TripAdvisor by comparing Portland hotel and flight prices. Travellers like you have written 18,175 reviews and posted 4,558 candid photos for Portland hotels. Book your Portland holiday today!
Or build your own Portland holiday package
The Press Hotel, Autograph Collection
#1 Hotel in Portland
The Press Hotel, Autograph Collection
The Press Hotel is a welcome addition to hotel options in Portland. At the budget level are the airport/Mall of Maine area hotels that are about what you would expect--basic but...
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Hilton Garden Inn Portland Downtown Waterfront
#2 Hotel in Portland
Hilton Garden Inn Portland Downtown Waterfront
We had a great stay at this hotel. The free breakfast was a plus. The room was very clean staff was extremely friendly I don't think you can find a nicer place in the Portland...
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Portland Harbor Hotel
#3 Hotel in Portland
Portland Harbor Hotel
We were celebrating two birthdays and this hotel made our stay in Portland perfect. The lounge areas were decorated for the holidays, which created a festive atmosphere, and...
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Cheap Flights to Portland
All Washington to Portland (WAS-PWM) fares found by travellers in the past 72 hours*
Dec
US$201 round trip
Jan
US$201 round trip
Feb
US$196 round trip
†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.