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Chatham Vacation Packages

Windmill in the mist from the beach on Pleasant Bay, Chatham
Lighthouse Beach, Chatham
Chatham Vacation Packages
Want to book a vacation to Chatham? Whether you're off for a romantic vacation, family trip, or an all-inclusive holiday, Chatham vacation packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect vacation package for Chatham on TripAdvisor by comparing Chatham hotel and flight prices. Travelers like you have written 5,040 reviews and posted 2,380 candid photos for Chatham hotels. Book your Chatham vacation today!
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Pleasant Bay Village
#1 Hotel in Chatham
Pleasant Bay Village
Make sure you spend at least an hour roaming around the property. This rivals any Japanese garden I have visited including San Francisco's, Brooklyn's and Chappaquiddick's. Look...
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The Chatham Motel
#2 Hotel in Chatham
The Chatham Motel
We stayed for 4 nights in mid-Sept in an Efficiency unit. It had 2 double beds, small dining table, fridge, microwave, mini stove, sink, dishes, pots, etc. Bathroom was remodeled...
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Hawthorne Motel
#3 Hotel in Chatham
Hawthorne Motel
“Lovely spot” 10/30/2014
Good off season value. Central to so much. Wouldn't choose the efficiency room again. Just a little too small but still kind of cute. Just didn't need the microwave, etc. I...
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Cheap Flights to Chatham
All Washington to Hyannis (WAS-HYA) fares found by travelers in the past 72 hours*
Dec
$237 round trip
Jan
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Feb
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†  Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers 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.