The Best Hotels with a Pool in Chatham, MA from AED 542 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

1. 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.

AED 1,077 total

includes taxes & fees

1 Sep - 2 Sep

2. Queen Anne Inn

Chatham

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

AED 958 total

includes taxes & fees

3 Sep - 4 Sep

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

3. 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.

AED 1,826 total

includes taxes & fees

31 Aug - 1 Sep

4. Pleasant Bay Village Resort

Chatham

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

AED 1,329 total

includes taxes & fees

12 Aug - 13 Aug

5. Chatham Bars Inn

Chatham

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

AED 4,393 total

includes taxes & fees

10 Aug - 11 Aug

6. 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.

AED 589 total

includes taxes & fees

1 Sep - 2 Sep

Seasonal outdoor pool, pool umbrellas, sun loungers

7. Holiday Hill Inn & Suites

Dennis Port

Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.

AED 480 total

includes taxes & fees

30 Aug - 31 Aug

8. 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.

AED 831 total

includes taxes & fees

1 Sep - 2 Sep

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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

"."

The Mariner Resort Cape Cod by The Red Collection

10/10 Excellent

"This property was very clean! There was a 9 hole golf course on the property that is free for guests to use so me and my family utilized it and had a blast! The pools and jacuzzi are very clean and you can smell the chlorine upon entering the pool area. I will be returning for future stays."

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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