Find 5 Star Hotels in Chatham, MA

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Check availability on Chatham 5 Star Hotels

Compare Chatham 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Chatham Bars Inn
Seasonal outdoor pool

Chatham Bars Inn

5.0 star property
9.2 out of 10, Wonderful, (753)
"Amazing place for a quick getaway or a long stay. The campus was gorgeous and the staff was delightful. "
The price is AED 1,389
AED 1,670 total
includes taxes & fees
1 May - 2 May
Chatham Bars Inn
Chatham Wayside Inn
Beach nearby

Chatham Wayside Inn

4.0 star property
9.2 out of 10, Wonderful, (478)
"Everything was great! Smart TVs would be nice. "
The price is AED 731
AED 984 total
includes taxes & fees
13 Apr - 14 Apr
Chatham Wayside Inn
Chatham Seafarer Inn
Beach nearby

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. "
The price is AED 629
AED 720 total
includes taxes & fees
11 Apr - 12 Apr
Chatham Seafarer Inn
Greyfinch Chatham Inn
Seasonal outdoor pool, sun loungers

Greyfinch Chatham Inn

3.0 star property
8.8 out of 10, Excellent, (214)
"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
Captain's House Inn
Suite, 1 Bedroom, Fireplace (Stable) | Premium bedding, individually decorated, individually furnished

Captain's House Inn

4.0 star property
9.8 out of 10, Exceptional, (177)
"Third visit over many years and still consistently high quality experience. We will be back again."
The price is AED 889
AED 1,018 total
includes taxes & fees
24 Apr - 25 Apr
Captain's House Inn
The Hawthorne
View from property

The Hawthorne

2.0 star property
9.4 out of 10, Exceptional, (177)
"Property is the best beachfront location for the price. Very clean. Beach is literally outside your front door and so easily accessible. Rooms were very clean. A 5 minute drive to Main Street Chatham with so many restaurants nearby. Would stay again. "
The price is AED 848
AED 971 total
includes taxes & fees
11 May - 12 May
The Hawthorne
Queen Anne Inn
Seasonal outdoor pool, pool umbrellas, sun loungers

Queen Anne Inn

4.0 star property
8.8 out of 10, Excellent, (228)
"Lovely property !! Helpful friendly staff! "
Queen Anne Inn
The Chatham Motel
Superior Room, 2 Double Beds, Kitchenette | Private kitchen | Fridge, coffee/tea maker

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
Old Harbor Inn
Hiking

Old Harbor Inn

3.5 star property
9.6 out of 10, Exceptional, (158)
"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 731
AED 837 total
includes taxes & fees
13 Apr - 14 Apr
Old Harbor Inn
Surfside Inn Chatham
Porch

Surfside Inn Chatham

2.5 star property
7.8 out of 10, Good, (134)
"Super cute property on a quiet side road. It's outdated, though that gives it most of its charm. Staff were super friendly and was greeted with wine and cheese when we arrived. The only issue was that I was not expecting the stairs to be so steep (was traveling with an older person). Right near the beach and walking distance to downtown Chatham."
Surfside Inn Chatham
Pleasant Bay Village Resort
Outdoor pool

Pleasant Bay Village Resort

3.0 star property
9.6 out of 10, Exceptional, (272)
"Property grounds were very beautiful and relaxing"
The price is AED 887
AED 1,015 total
includes taxes & fees
11 May - 12 May
Pleasant Bay Village Resort
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Learn more about Chatham

With glimmering waters perfect for sailing, swimming and fishing, this idyllic beach town exudes laid-back charm.

See all hotels in Chatham
Chatham showing a house and boating

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chatham?
How much you pay for a 5-star hotel in Chatham can vary depending on when you prefer to travel and how long you plan to be away, among several factors. Use our price per night filter and other search tools to find the best deal on an indulgent stay.

  • Search for the lowest price per night

What makes a hotel 5 stars in Chatham?
From high-end restaurants and 24-hour gyms to swimming pools and superior bedding, the 5-star experience in Chatham is all about luxury and comfort. But it requires more than just upscale amenities to get a 5-star rating. Hotels must also deliver superb guest-centric services like in-room massages, laundry and dry cleaning and 24-hour concierge services.
Are there any 5-star all-inclusive resorts in Chatham?
Use our handy filters to find an upscale escape in Chatham where most of what you need is included in the price. From there, narrow down your results for properties that have a rating of 5 stars and are listed as “All inclusive.” The first thing on the to-do list at these stays? Pure enjoyment and indulgence.
Are there any 5-star vacation rentals in Chatham?
Our site doesn’t offer any 5-star vacation rentals in Chatham. However, you will still find some top-rated escapes where the only item on your agenda will be to kick back and enjoy yourself. Discover what’s available by browsing our vacation rentals in Chatham.