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

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Check availability on Chatham Hotels with a Pool

Our top choices for Chatham hotels with a pool

Seasonal outdoor pool, sun loungers

Greyfinch Chatham Inn

Greyfinch Chatham Inn
3.0 star property
Chatham
8.8 out of 10, Excellent, (271 reviews)
  • cleanliness
    Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
The price is ₩536,855
₩669,193 total
includes taxes & fees
Jul 29 - Jul 30
Greyfinch Chatham Inn
Seasonal outdoor pool

The Chatham Motel

The Chatham Motel
2.0 star property
Chatham
9.2 out of 10, Wonderful, (633 reviews)
  • cleanliness
    Soak up summer vibes in this Cape Cod retreat with a seasonal outdoor pool, playground, and peaceful garden setting.
The price is ₩452,238
₩517,584 total
includes taxes & fees
Jul 20 - Jul 21
The Chatham Motel
Sundeck

Queen Anne Inn

Queen Anne Inn
4.0 star property
Chatham
8.8 out of 10, Excellent, (249 reviews)
  • cleanliness
    Victorian oasis offers seasonal outdoor pool with comfortable loungers and shaded umbrellas.
The price is ₩452,088
₩517,416 total
includes taxes & fees
Jul 20 - Jul 21
Queen Anne Inn
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers

Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (708 reviews)
  • cleanliness
    Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
The price is ₩742,641
₩914,985 total
includes taxes & fees
Jul 19 - Jul 20
Chatham Wayside Inn
Outdoor pool

Pleasant Bay Village Resort

Pleasant Bay Village Resort
3.0 star property
Chatham
9.6 out of 10, Exceptional, (319 reviews)
  • cleanliness
    Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
The price is ₩610,334
₩698,527 total
includes taxes & fees
Jul 19 - Jul 20
Pleasant Bay Village Resort
Seasonal outdoor pool

Chatham Bars Inn

Chatham Bars Inn
5.0 star property
Chatham
9.2 out of 10, Wonderful, (845 reviews)
  • cleanliness
    Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
The price is ₩1,547,325
₩1,770,915 total
includes taxes & fees
Aug 12 - Aug 13
Chatham Bars Inn
Property grounds

The Escape Inn

The Escape Inn
2.5 star property
Bass River
9.4 out of 10, Exceptional, (717 reviews)
  • cleanliness
    Immerse in a refreshing summer retreat at this clean, seasonal pool oasis with beach-themed charm.
The price is ₩275,484
₩315,296 total
includes taxes & fees
Jul 15 - Jul 16
The Escape Inn
View from property

Ocean Street Inn on Hyannis Harbor

Ocean Street Inn on Hyannis Harbor
2.0 star property
Hyannis
7.0 out of 10, Good, (817 reviews)
  • cleanliness
    Seaside serenity awaits at this harbor-front motel, where nearby pools and marina access promise refreshing coastal relaxation.
The price is ₩209,495
₩263,732 total
includes taxes & fees
Jul 15 - Jul 16
Ocean Street Inn on Hyannis Harbor
Outdoor pool

GuestLodge

GuestLodge
2.0 star property
West Dennis
8.0 out of 10, Very Good, (547 reviews)
  • cleanliness
    Refreshing pool oasis awaits at Cape Cod motel with aquatic fun just steps from beaches.
The price is ₩152,266
₩174,272 total
includes taxes & fees
Jul 27 - Jul 28
GuestLodge
Indoor pool

Courtyard Resort

Courtyard Resort
2.0 star property
Hyannis
8.6 out of 10, Excellent, (100 reviews)
  • cleanliness
    Resort relaxation awaits with hot tub, indoor pool at Cape Cod getaway near Hyannis Harbor.
The price is ₩282,555
₩323,385 total
includes taxes & fees
Jul 16 - Jul 17
Courtyard Resort
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.
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Choose what matters most at hotels with a pool in Chatham

Breakfast included
Hot tub

Top Chatham Hotel Reviews

All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

10/10 Excellent
"Beds were comfortable. We liked both the indoor and outdoor pools. Great location. We’d definitely stay again."
Melanie 2-night trip
Posted 2 hours ago
All Seasons Resort, Trademark Collection by Wyndham

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.