Find Historic Hotels in Chatham, MA

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Pick from 14 Chatham Historic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Greyfinch Chatham Inn
Outdoor pool
Greyfinch Chatham Inn
3.0 star property
8.8 out of 10, Excellent, (213)
"I really enjoyed my three night stay here while I attended a painting workshop at the Creative Arts Centre. The rooms have been totally renovated and it was a very well done reno. Very clean and in a convenient location. Love the big walk in shower with the rain shower head. There is a Keurig coffee machine and a refrigerated drawer. I didn't want to have to eat out all of the time so picked up prepared hot meals from the market close by. I would stay there again as it's a lovely place and a...
Greyfinch Chatham Inn
Charming Downtown Chatham
Living area
Charming Downtown Chatham
10.0 out of 10, Exceptional, (35)
"Exactly what we wanted for a long weekend! Shopping on Main Street and walking distance to the Chatham Lighthouse. Clean and comfortable stay. Host was pleasant and communicaton was easy!"
Charming Downtown Chatham
Chatham Bars Inn
Exterior
Chatham Bars Inn
5.0 star property
9.2 out of 10, Wonderful, (729)
"Location, service, food, and amenities are all top notch. The complimentary limo service needs extra mention as it was impeccable: brand new cars, local drivers, fast and reliable. Made for a very enjoyable stay. Thanks"
The price is AED 1,124
AED 1,351 total
includes taxes & fees
6 Nov - 7 Nov
Chatham Bars Inn
Queen Anne Inn
Room
Queen Anne Inn
4.0 star property
8.8 out of 10, Excellent, (227)
"Lovely property !! Helpful friendly staff! "
Queen Anne Inn
Pleasant Bay Village Resort
Outdoor spa tub
Pleasant Bay Village Resort
3.0 star property
9.6 out of 10, Exceptional, (272)
"Property grounds were very beautiful and relaxing"
Pleasant Bay Village Resort
The Chatham Motel
Room
The Chatham Motel
2.0 star property
9.2 out of 10, Wonderful, (601)
"This place is a real gem. We loved our stay and will definitely return."
The Chatham Motel
Captain's House Inn
Property grounds
Captain's House Inn
4.0 star property
9.8 out of 10, Exceptional, (173)
"What a special stay at the Captain’s Inn. A beautiful accommodation and a very well take care of inn. We can not wait to return "
The price is AED 1,154
AED 1,320 total
includes taxes & fees
24 Nov - 25 Nov
Captain's House Inn
Chatham Seafarer Inn
Front of property
Chatham Seafarer Inn
3.5 star property
9.0 out of 10, Wonderful, (285)
"I really liked my stay at the Seafarer! Such a cute spot and the people were super nice. I was in town visiting family, so my room was the perfect convenience with a cute little spot to sit outside my room and sip coffee in the morning and watch the world go by. The bed was comfortable, and it was a short distance to downtown Chatham where I could run to Chatham Light. Highly recommend. "
Chatham Seafarer Inn
Old Harbor Inn
Exterior detail
Old Harbor Inn
3.5 star property
9.6 out of 10, Exceptional, (157)
"Judy and Ray were so warm and welcoming. The property was pristine, quiet, and very conveniently located to town. I would highly recommend this stay from someone who wants a touch of luxury with a home like feel."
The price is AED 915
AED 1,047 total
includes taxes & fees
6 Nov - 7 Nov
Old Harbor Inn
Chatham Wayside Inn
Front of property
Chatham Wayside Inn
4.0 star property
9.2 out of 10, Wonderful, (445)
"Fabulous hotel in a beautiful location. "
The price is AED 731
AED 984 total
includes taxes & fees
6 Nov - 7 Nov
Chatham Wayside 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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Frequently asked questions

What should I expect on my historical trip to Chatham?
You’ll probably want to seek out the historically relevant sites during your vacation in Chatham. While you’re here, you can visit the waterfront and seaside. During your stay in this trendy area, you can also relish a trip to the seafood restaurants.
How many historically relevant hotels will I find in Chatham?
In Chatham, you’ll find 358 hotels and other accommodations bookable on Expedia though you won’t find many designated historic hotels.
What are the must-see historical sites and other places to visit in Chatham?
Chatham is notable for landmarks like Chatham Lighthouse, Chatham Lighthouse Beach, and Mayo House. Cultural venues include Gallery Antonia, Monomoy Theatre, and Chatham Railroad Museum. A couple of additional sights to add to your agenda are Chatham Fish Pier and Ridgevale Beach.
What is a historic hotel like in Chatham?
Guests who book a historic hotel can stay someplace that has an officially recognized national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be identified as a historic hotel as long as it’s of special interest. Traditional architecture and period features can be admired in the guestrooms or communal spaces of historic hotels in Chatham, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is a term often used in Asia and Europe, while “historic hotel” is a term often used in the U.S. though overall the terms are quite similar. The building and architecture of historic hotels are generally what’s most important. For a heritage hotel, mainly, it’s cultural value as well as how it shaped the community.
Do historic hotels in Chatham have modern facilities?
Hotels include modern conveniences and safety features you’ve come to expect, but every effort is made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the popular amenities found in any hotel will also be available in a historic hotel. When you choose a historic hotel in Chatham, don’t worry that you’ll find a place that’s uncomfortable or rundown.