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

Find Hotels with a Pool in Chatham, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chatham Hotels with a Pool

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Chatham hotels with a pool

A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.

1. Chatham Bars Inn

Chatham Bars Inn
5.0 star property
Chatham
9.2 out of 10, Wonderful, (876 reviews)
"Amazing property and staff."
United States
Sylvia
The price is ￥55,579
￥63,611 total
includes taxes & fees
Nov 29 - Nov 30
Chatham Bars Inn
A swimming pool with lounge chairs and a white fence.

2. Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (763 reviews)
"Amazing stay!!"
Canada
Ashley
The price is ￥25,383
￥35,903 total
includes taxes & fees
Dec 1 - Dec 2
Chatham Wayside Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub

Top Chatham Hotel Reviews

Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Great location"
Gary 1-night trip
Posted 7 hours ago
Hyannis Harbor Hotel

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?
Spend some time experiencing the great outdoors at Chatham Lighthouse Beach and Ridgevale Beach. During your stay, check out sights such as Chatham Lighthouse, Cape Cod Beaches, and Cape Cod National Seashore. 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.