Find Hotels with a Pool in Chatham, MA

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Our top choices for Chatham hotels with a pool

Greyfinch Chatham Inn

Greyfinch Chatham Inn
3.0 star property
Chatham
8.8 out of 10, Excellent, (254 reviews)
  • cleanliness
    Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
$166 nightly
The price is $190
May 5 - May 6
Total with taxes and fees
Greyfinch Chatham Inn

Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (650 reviews)
  • cleanliness
    Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
$199 nightly
The price is $228
Apr 26 - Apr 27
Total with taxes and fees
Chatham Wayside Inn

Chatham Seafarer Inn

Chatham Seafarer Inn
3.5 star property
Chatham
9.0 out of 10, Wonderful, (319 reviews)
  • cleanliness
    Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$154 nightly
The price is $176
Apr 26 - Apr 27
Total with taxes and fees
Chatham Seafarer Inn

Pleasant Bay Village Resort

Pleasant Bay Village Resort
3.0 star property
Chatham
9.6 out of 10, Exceptional, (304 reviews)
  • cleanliness
    Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
$213 nightly
The price is $243
May 7 - May 8
Total with taxes and fees
Pleasant Bay Village Resort

Chatham Bars Inn

Chatham Bars Inn
5.0 star property
Chatham
9.2 out of 10, Wonderful, (817 reviews)
  • cleanliness
    Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
$376 nightly
The price is $430
Apr 16 - Apr 17
Total with taxes and fees
Chatham Bars Inn

The Escape Inn

The Escape Inn
2.5 star property
Bass River
9.4 out of 10, Exceptional, (679 reviews)
  • cleanliness
    Immerse in a refreshing summer retreat at this clean, seasonal pool oasis with beach-themed charm.
$80 nightly
The price is $92
Apr 13 - Apr 14
Total with taxes and fees
The Escape Inn

Hyannis Travel Inn

Hyannis Travel Inn
2.5 star property
Hyannis
9.6 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Splash into summer at this Cape Cod oasis with refreshing indoor and outdoor pools.
$89 nightly
The price is $102
Apr 27 - Apr 28
Total with taxes and fees
Hyannis Travel Inn

Ocean Club on Smuggler's Beach

Ocean Club on Smuggler's Beach
2.5 star property
Bass River
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Refreshing indoor pool and hot tub escape steps away from a dreamy private beach setting.
$134 nightly
The price is $152
Apr 13 - Apr 14
Total with taxes and fees
Ocean Club on Smuggler's Beach

🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (11 reviews)
  • cleanliness
    Indoor pool and beachfront access in Cape Cod cottage offer relaxing escape near Thumpertown Beach and trails.
$342 nightly
The price is $391
Apr 15 - Apr 16
Total with taxes and fees
🐚The Bay Cottage on Thumpertown Beach

All Seasons Resort

All Seasons Resort
Bass River
9.0 out of 10, Wonderful, (58 reviews)
$113 nightly
The price is $129
Apr 13 - Apr 14
Total with taxes and fees
All Seasons 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.

Choose what matters most at hotels with a pool in Chatham

Top Chatham Hotel Reviews

Frequently asked questions

What are the best hotels in Chatham with outdoor pools?
Pleasant Bay Village Resort is a charming 3-star hotel that offers an inviting outdoor pool, superb for families looking to unwind and enjoy the sun. Guests have raved about the comfortable and clean rooms, as well as the friendly and attentive staff, achieving an outstanding score of 9.6. The beautifully landscaped grounds add to the resort's appeal, making it a serene getaway.

For those seeking a more luxurious experience, Chatham Bars Inn stands out as a premier 5-star hotel. This hotel not only features a stunning outdoor pool but also offers a private beach, an array of top amenities, and exceptional service. With a traveller rating of 9.2, visitors appreciate the exquisite food, beautiful location, and the staff's willingness to go above and beyond to enhance their stay.

Chatham Wayside Inn, a delightful 4-star hotel, is another fantastic option boasting an outdoor pool. Guests love the charming and clean rooms, along with the friendly staff who are always ready to assist. With a review rating of 9.2, the included complimentary breakfast adds great value for families looking to start their day right before exploring the local attractions.

Each of these hotels provides unique features and a warm atmosphere, making them excellent choices for families seeking a memorable stay in Chatham.
How much does a hotel with outdoor pool in Chatham cost?
Enjoy staying in a hotel in Chatham with an outdoor pool. You can find a great deal from $92 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What are some of the best Chatham hotels with outdoor pools and scenic views?
Chatham Bars Inn is a stunning 5-star retreat that offers an unforgettable experience for travellers seeking outdoor pools combined with breathtaking views. With a remarkable review rating of 9.2, guests rave about the excellent service and the beautiful location, making it an ideal choice for families and adventure-seekers alike.

This exquisite hotel boasts a gorgeous outdoor pool that overlooks the serene landscape, allowing you to soak in the sun while enjoying the picturesque surroundings. Families can take advantage of the private beach access, great for a day of fun in the sand, or enjoy a game of tennis on-site. The spacious rooms feature premium bedding and designer toiletries, ensuring a comfortable and luxurious stay.

Moreover, the inn's top amenities extend to a relaxing massage service, making it easy for parents to unwind while the kids splash around in the pool. Dining options are also highly praised, with guests noting the exceptional quality of the food available, enhancing the overall experience at this remarkable destination.
Is it cheaper to book flights and a Chatham hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
How can I save on a Chatham hotel with a pool with Expedia?
Before booking your Chatham hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Chatham for you.

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