Hotels with Swimming Pool, Chatham Massachusetts

Q: What are some accommodations with pools in Chatham?

Chatham Bars Inn : Resort, 4-minute walk from Cape Cod Beaches. Features a private beach, a seasonal outdoor pool, and a full-service spa. Chatham Wayside Inn : Hotel, 11-minute walk from Cape Cod Beaches. Offers daily, a seasonal outdoor pool, and free self parking. The Chatham Motel : Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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Our top choices for Chatham hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers

Queen Anne Inn

Chatham

Victorian oasis offers seasonal outdoor pool with comfortable loungers and shaded umbrellas.

P21,423 total

includes taxes & fees

Jul 28 - Jul 29

Pleasant Bay Village Resort

Chatham

Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.

P28,662 total

includes taxes & fees

Jul 15 - Jul 16

Greyfinch Chatham Inn

Chatham

Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.

P28,857 total

includes taxes & fees

Aug 2 - Aug 3

Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers

Chatham Wayside Inn

Chatham

Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.

P37,714 total

includes taxes & fees

Jul 5 - Jul 6

The Chatham Motel

Chatham

Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.

P21,237 total

includes taxes & fees

Jul 15 - Jul 16

Chatham Bars Inn

Chatham

Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.

P73,008 total

includes taxes & fees

Jul 22 - Jul 23

Charm on Main by Ocean Edge

Sea Pines

Escape to a white sand beach retreat with a seasonal outdoor pool, sun loungers, and umbrellas just steps from the shore.

P21,077 total

includes taxes & fees

Jul 6 - Jul 7

Kingfisher Lodging

Dennis

Splash into summer fun with this clean Cape Cod motel's seasonal outdoor pool.

P17,182 total

includes taxes & fees

Jul 6 - Jul 7

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Choose what matters most at hotels with a pool in Chatham

Breakfast included

Hot tub

Top Chatham Hotel Reviews

The Corsair & Cross Rip Oceanfront Resort

8/10 Good

"Lots of kids , I guess more of a family type place . Which kept me from the pool. That’s my only negative. If you are with the family it’s probably perfect ."

Bayside Resort Hotel

8/10 Good

"Facility overall was clean, but older rugs and hand rails could have been cleaner. Room was not cleaned on second day after do not disturb sign was removed shortly after breakfast. The Breakfast itself was reasonable, but there were items that ran out because crew could not easily keep up with the demand. Location is very good, did not use the pools but they appeared to be enjoyed by those who did."

Chatham Wayside Inn

8/10 Good

"Beautiful hotel with very convenient location on main street. Only downside was paying extra for a pack n play and the upgrade to a balcony was not worth it- no view. Wish the pool area was a little nicer. Otherwise would recommend for the spacious king room, restaurant, and location. Very accommodating staff!"

Red Jacket Beach Resort

8/10 Good

"Our family of four adults and three children rented a townhouse with three bedrooms. an annoying thing was the unit was not supplied with items like a vegetable peeler. These units are not meant for real cooking, but traveling with young kids, you might want to make salads for lunch or part of a simple dinner. No pots and pans or kitchen utensils in general. Serve ware was limited."

Hyannis Harbor Hotel

10/10 Excellent

"We had a great stay. Alicia at the front desk was excellent servicing us with our every need while we were there, she’s very pleasant and super helpful. All the other staff were also friendly that we interacted with. The property was clean and well kept, room was cozy l aside from a small hiccup with one of the bed sheets that was a little dirty. That was replaced with no problem when brought to Alicia’s attention. Would stay here again"

Holiday Hill Inn & Suites

8/10 Good

"Well situated near the main areas. The bed was extremely comfortable for a good night sleep after a long day at the beach. However, it is a bit outdated. Everything worked fine but it’s definitely a classic old school motel vibe so just expect it! Overall would stay again, the staff was helpful and the place was cozy."