The Best Hotels with a Pool in Chatham, MA from NT$7,311 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.

NT$57,710 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.

NT$11,854 total

includes taxes & fees

Aug 12 - Aug 13

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.

NT$20,578 total

includes taxes & fees

Aug 17 - Aug 18

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.

NT$13,847 total

includes taxes & fees

Jul 29 - Jul 30

The Chatham Motel

Chatham

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

NT$11,176 total

includes taxes & fees

Aug 24 - Aug 25

Queen Anne Inn

Chatham

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

NT$10,334 total

includes taxes & fees

Aug 18 - Aug 19

Wequassett Resort and Golf Club

Harwich

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

NT$60,403 total

includes taxes & fees

Jul 27 - Jul 28

Olde Tavern Motel And Inn

Orleans

Soak in coastal charm at the seasonal outdoor pool surrounded by lush garden views at this beautifully renovated motel.

NT$7,463 total

includes taxes & fees

Jul 27 - Jul 28

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Choose what matters most at hotels with a pool in Chatham

Breakfast included

Hot tub

Top Chatham Hotel Reviews

The Mariner Resort Cape Cod by The Red Collection

8/10 Good

"Just the receptionists were unfriendly"

All Seasons Resort, Trademark Collection by Wyndham

8/10 Good

"Great hotel on the Cape. It was convenient, priced well, the rooms were updated and clean and the swimming pools both inside and out were great. After we left the hotel, my son realized he left his wallet on the nightstand. I called and the woman at the front desk who was working on Friday, July 17th made a special trip to the room, retrieved the wallet and had it waiting for my son when he arrived. Great service from start to finish. Thank you!"

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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