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Chatham Holiday Packages

Windmill in the mist from the beach on Pleasant Bay, Chatham
Lighthouse Beach, Chatham
Chatham Holiday Packages
Want to book a holiday to Chatham? Whether you're off for a romantic holiday, family trip, or an all-inclusive holiday, Chatham holiday packages on TripAdvisor make planning your trip simple and affordable.
Find the perfect holiday package for Chatham on TripAdvisor by comparing Chatham hotel and flight prices. Travellers like you have written 8,215 reviews and posted 1,754 candid photos for Chatham hotels. Book your Chatham holiday today!
Or build your own Chatham holiday package
Chatham Inn At 359 Main
#1 Hotel in Chatham
Chatham Inn At 359 Main
We found this quaint inn on the internet when we had to leave Nantucket quickly due to a tropical storm. It is immaculate, charming, and quiet. The service was very attentive...
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Pleasant Bay Village
#2 Hotel in Chatham
Pleasant Bay Village
First, Management was very helpful when delayed flights caused me to arrive 3 days later than intended. Even though they couldn't refund me, they tried to rebook my rooms. They...
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The Chatham Motel
#3 Hotel in Chatham
The Chatham Motel
By far this is the cleanest facility we have ever been in. (And we've been in all kinds - we usually like B&B's but couldn't find availability on short notice). This is our 2nd...
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Cheap Flights to Chatham
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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 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.