Find Hotels with a Pool in Chatham, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Our top choices for Chatham hotels with a pool

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

Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (602)
"Super cozy and clean with fantastic staff and great location loved everyday spent here "
United States
noushin
Chatham Wayside Inn
Seasonal outdoor pool
Chatham Bars Inn

Chatham Bars Inn

Chatham Bars Inn
5.0 star property
Chatham
9.2 out of 10, Wonderful, (797)
"Great accommodation and staff."
United States
Michael
The price is AED 955
AED 1,148 total
includes taxes & fees
17 Dec - 18 Dec
Chatham Bars Inn
Property grounds
The Escape Inn

The Escape Inn

The Escape Inn
2.5 star property
Bass River
9.4 out of 10, Exceptional, (653)
"One of the best hotels I stayed at "
United States
Robert
The price is AED 330
AED 377 total
includes taxes & fees
12 Dec - 13 Dec
The Escape Inn
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Bayside Resort Hotel

Bayside Resort Hotel

Bayside Resort Hotel
3.0 star property
West Yarmouth
8.8 out of 10, Excellent, (1520)
"excellent quality of food. Pool and hot tub fabulous"
United States
Deborah
Bayside Resort Hotel
Exterior
Hyannis Plaza Hotel

Hyannis Plaza Hotel

Hyannis Plaza Hotel
2.5 star property
Hyannis
7.0 out of 10, Good, (966)
"good stay for night"
United States
David
The price is AED 262
AED 337 total
includes taxes & fees
9 Jan - 10 January 2026
Hyannis Plaza Hotel
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Hampton Inn & Suites Cape Cod-West Yarmouth

Hampton Inn & Suites Cape Cod-West Yarmouth

Hampton Inn & Suites Cape Cod-West Yarmouth
2.5 star property
West Yarmouth
8.8 out of 10, Excellent, (1000)
"Excellent stay."
United States
Patricia
The price is AED 379
AED 434 total
includes taxes & fees
7 Jan - 8 January 2026
Hampton Inn & Suites Cape Cod-West Yarmouth
Indoor pool
Courtyard Resort

Courtyard Resort

Courtyard Resort
2.0 star property
Hyannis
8.2 out of 10, Very Good, (43)
"Room was very clean. Staff were courteous!"
United States
Timothy
The price is AED 400
AED 458 total
includes taxes & fees
17 Dec - 18 Dec
Courtyard Resort
Exterior
Cape Sands Inn

Cape Sands Inn

Cape Sands Inn
2.5 star property
West Yarmouth
8.2 out of 10, Very Good, (1013)
"I love this hotel clean good up keep "
United States
Jerome
The price is AED 252
AED 288 total
includes taxes & fees
14 Dec - 15 Dec
Cape Sands Inn
Indoor pool, seasonal outdoor pool, sun loungers
Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth
3.0 star property
West Yarmouth
8.0 out of 10, Very Good, (1000)
"Nice place and good options for breakfast "
United States
Jennifer
The price is AED 356
AED 407 total
includes taxes & fees
17 Dec - 18 Dec
Aiden by Best Western Cape Cod - West Yarmouth
Deluxe Suite, Oceanfront, 2 Bedrooms | Terrace/patio
Ocean Club on Smuggler's Beach

Ocean Club on Smuggler's Beach

Ocean Club on Smuggler's Beach
2.5 star property
Bass River
9.2 out of 10, Wonderful, (1001)
"The Ocean Club is always a great place to stay. Very convenient location and a great place for a walk on the beach. "
United States
Steve
The price is AED 547
AED 665 total
includes taxes & fees
14 Dec - 15 Dec
Ocean Club on Smuggler's Beach
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

Top Chatham Hotel Reviews

Captain's House Inn

Captain's House Inn

10/10 Excellent
"All was perfect. Beautiful property and outstanding staff. "
David 3-night trip
Posted 1 day ago
Captain's House Inn

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Chatham?
Chatham Wayside Inn: Features daily, a seasonal outdoor pool, and free self parking. Chatham Bars Inn: Offers a private beach, a seasonal outdoor pool, and a full-service spa. 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.