The Best Hotels with a Pool in Chatham, MA from ￥35,339 in 2026

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.

A boat on a calm river, a large house with a red roof, and dense greenery in the background.

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Our top choices for Chatham hotels with a pool

Chatham Bars Inn

Chatham

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

￥195,391 total

includes taxes & fees

Aug 17 - Aug 18

Pleasant Bay Village Resort

Chatham

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

￥54,520 total

includes taxes & fees

Aug 13 - Aug 14

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.

￥81,708 total

includes taxes & fees

Aug 30 - Aug 31

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.

￥51,251 total

includes taxes & fees

Aug 30 - Aug 31

Queen Anne Inn

Chatham

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

￥48,345 total

includes taxes & fees

Aug 25 - Aug 26

Wequassett Resort and Golf Club

Harwich

Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.

Rodeway Inn Orleans - Cape Cod

Orleans

Splash into refreshing luxury with a clean, spacious pool perfect for sunny Cape Cod afternoons.

￥40,385 total

includes taxes & fees

Aug 2 - Aug 3

Skaket Beach Motel

Orleans

Dive into relaxation at this coastal motel's seasonal outdoor pool, just steps from beautiful Skaket Beach and sunset views.

￥41,134 total

includes taxes & fees

Aug 24 - Aug 25

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Choose what matters most at hotels with a pool in Chatham

Breakfast included

Hot tub

Top Chatham Hotel Reviews

Cape Sands Inn

10/10 Excellent

"Very clean! The workers were kind. Will definitely be back!"

Margaritaville Resort Cape Cod

8/10 Good

"The staff were wonderful at check in. The room was very clean and spacious for our family of four. The room was cool and pretty dark when it was time to sleep. The room doors do slam pretty hard, and that can wake you up. The smores nights in the courtyard was nice. The pool was clean and not too deep. The place was very family friendly. Arcade was okay, a little pricey for what it was. I wish the buffet breakfast was included in the cost of the room, it was $16 per adult and about $10-$12 per kid. The restaurants there had good desserts and drinks(we didn’t have a meal there) The area was great easy access to a lot of things. Perfect family resort. Would definitely go back."

Freebird Motor Lodge by Reverie Boutique Collection

10/10 Excellent

"The rooms were so clean and the beds were so comfortable. The amenities with the indoor and outdoor pool were great . The fire pits at night were so relaxing. So close to everything especially the Water park right across the street. Would definitely stay here again. Staff so friendly and welcoming."

Red Jacket Beach Resort

10/10 Excellent

"Beautiful clean resort right on the beach. Staff to help set up complimentary umbrella and chairs on the beach. Drink and food service on the beach as well. Staff greeted us with a smile and offered to help with luggage. Check in process went smoothly with the help of Marina. Marina and RJ team also went out of their way to help us decorate our room to surprise our friends for their 50th birthdays. We also received a box of chocolate and card from them, very kind gesture. We had a great time and look forward to coming back next year. Thank you again to Marina and RJ team for making our stay special and memorable!"

Frequently asked questions

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.

What is there to see and do in Chatham?

Explore places like Cape Cod Beaches and Cape Cod National Seashore while you're in Chatham. Make a point to visit attractions like Chatham Lighthouse Beach and Chatham Railroad Museum. Visitors to Chatham speak highly of the natural attractions, including the beautiful beaches.

When is the best time to book a hotel with a pool in Chatham?

Taking into account the local weather in Chatham is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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.

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