Chatham Trips (flight + hotel)

Chatham Beach Vacation

There's nothing that can beat a Chatham vacation. Whether you're indulging in fancy cocktails at a local hot spot or flipping through a book by the shore, your trip to Chatham is the perfect time to live out your beachy dreams. Many travelers will tell you to stay near Ridgevale Beach, located just 3 kilometers from the town center. However, you'll also find a fantastic range of Chatham vacation packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Top hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is P22,415 per night from Apr 9 to Apr 10
P22,415
P25,654 total
Apr 9 - Apr 10
includes taxes & fees
9.2/10 Wonderful! (815 reviews)
Loved everything about it. Beautiful location, cozy room with elegant bathroom, polite and lovely staff, excellent food! Server Bevin was the best!!

Reviewed on Mar 19, 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is P9,707 per night from Mar 31 to Apr 1
P9,707
P13,730 total
Mar 31 - Apr 1
includes taxes & fees
9.2/10 Wonderful! (645 reviews)
A lovely place to stay in downtown Chatham

Reviewed on Mar 22, 2026

Chatham Wayside Inn
Captain's House Inn

Captain's House Inn

4 out of 5
369 Old Harbor Road Chatham MA
9.8/10 Exceptional! (216 reviews)
The fireplace and a glass of wine made a cozy evening.

Reviewed on Mar 22, 2026

Captain's House Inn
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.

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What to do in Chatham

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.