1. Chatham Wayside Inn

- Location: Chatham
- Guest rating: 9.2/10 (Wonderful, 767 reviews)
- Price: $223 nightly, $255 total, Nov 15 - Nov 16, Total with taxes and fees, for Recommended hotels in Chatham
- Review: Amazing stay!!, by Ashley
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Check prices for these dates, December 13 – 14, 2026
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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.
Stroll the historic Main Street lined with boutiques, then head to Lighthouse Beach for seal-spotting at low tide. Seafood shacks serve the freshest catch, while the Chatham Bandstand hosts free summer concerts that locals never miss.


















Our travelers like these places to stay in the area, and they may have budget-friendly room rates: Chatham Bars Inn - 0.5 mi (0.9 km) from the heart of Chatham. Property features at this hotel include free breakfast, free WiFi, and free parking. Chatham Wayside Inn - 0.3 mi (0.4 km) from the heart of Chatham. Guests can enjoy free WiFi, free parking, and a 24-hour front desk at this motel. Queen Anne Inn - 0.3 mi (0.4 km) from the heart of Chatham. Close to public transit, this property is within a 10-minute walk of Hyannis Transportation Center. You can take advantage of free breakfast, free WiFi, and free parking at this hotel. Greyfinch Chatham Inn - 0.5 mi (0.9 km) from the heart of Chatham. Located within a 20-minute walk of Cape Cod Beaches. Property features at this hotel include free breakfast, free WiFi, and free parking. Pleasant Bay Village Resort - 2.4 mi (3.8 km) from the heart of Chatham. Located within a 20-minute walk of Cape Cod Beaches. Property features at this motel include free WiFi, free parking, and an indoor pool.
The weather is important when you're experiencing new places, so here's a little information that might be helpful: The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches.
Depending on your interests, you might like to check out these things around Chatham. Get out into nature with places like Chatham Lighthouse Beach, Ridgevale Beach, and Cape Cod Beaches. Cultural attractions include Chatham Railroad Museum, Chatham Drama Guild, and Atwood House Museum. Visit landmarks like Chatham Lighthouse and Mayo House.
Keep this information about transit options in and around Chatham in your back pocket to make the most of your stay: You can search for flights to the closest airport, which is Hyannis, MA (HYA-Barnstable Municipal), located 16.8 mi (27 km) from the city center. An alternative is Nantucket, MA (ACK-Nantucket Memorial), which is 29.9 mi (48.1 km) away.