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

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

Our top choices for Chatham hotels with a pool

A swimming pool with lounge chairs and a white fence.

1. Chatham Wayside Inn

Chatham Wayside Inn
4.0 star property
Chatham
9.2 out of 10, Wonderful, (760 reviews)
  • cleanliness
    Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
$217 nightly
The price is $248
Nov 10 - Nov 11
Total with taxes and fees
Chatham Wayside Inn
A rectangular swimming pool with a tiled deck, surrounded by lounge chairs and umbrellas, set against a backdrop of dense green trees.

2. Greyfinch Chatham Inn

Greyfinch Chatham Inn
3.0 star property
Chatham
8.8 out of 10, Excellent, (299 reviews)
  • cleanliness
    Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
$203 nightly
The price is $233
Nov 1 - Nov 2
Total with taxes and fees
Greyfinch Chatham Inn
A resort pool with multiple sun loungers and umbrellas, surrounded by beach views and boats.

3. Chatham Bars Inn

Chatham Bars Inn
5.0 star property
Chatham
9.2 out of 10, Wonderful, (873 reviews)
  • cleanliness
    Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
$387 nightly
The price is $443
Nov 2 - Nov 3
Total with taxes and fees
Chatham Bars Inn
A swimming pool with clear blue water, surrounded by blue and white lounge chairs.

4. Chatham Seafarer Inn

Chatham Seafarer Inn
3.5 star property
Chatham
9.0 out of 10, Wonderful, (355 reviews)
  • cleanliness
    Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$259 nightly
The price is $296
Oct 28 - Oct 29
Total with taxes and fees
Chatham Seafarer Inn
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.

5. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
5.0 star property
Harwich
9.4 out of 10, Exceptional, (280 reviews)
  • cleanliness
    Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.
$381 nightly
The price is $436
Nov 27 - Nov 28
Total with taxes and fees
Wequassett Resort and Golf Club
An indoor swimming pool with blue lounge chairs and a tiled wall with a checkered pattern.

6. The Villages at Ocean Edge

The Villages at Ocean Edge
3.5 star property
Brewster
8.4 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Dive into paradise with 7 amazing pools, each offering a different vibe for every vacation mood.
$156 nightly
The price is $178
Nov 9 - Nov 10
Total with taxes and fees
The Villages at Ocean Edge
A swimming pool with lounge chairs and a covered seating area.

7. Pelham on Earle

Pelham on Earle
3.0 star property
West Harwich
9.4 out of 10, Exceptional, (110 reviews)
  • cleanliness
    Coastal getaway with a seasonal outdoor pool where relaxation awaits after exploring Cape Cod's beautiful beaches.
$204 nightly
The price is $234
Oct 28 - Oct 29
Total with taxes and fees
Pelham on Earle
A swimming pool with a fenced area, lounge chairs, and a building in the background.

8. Skaket Beach Motel

Skaket Beach Motel
2.0 star property
Orleans
9.2 out of 10, Wonderful, (505 reviews)
  • cleanliness
    Dive into relaxation at this coastal motel's seasonal outdoor pool, just steps from beautiful Skaket Beach and sunset views.
$113 nightly
The price is $129
Nov 3 - Nov 4
Total with taxes and fees
Skaket Beach Motel
A clear blue swimming pool with a metal ladder, surrounded by lounge chairs and an American flag.

9. A Beach Breeze Inn

A Beach Breeze Inn
2.5 star property
West Harwich
9.6 out of 10, Exceptional, (298 reviews)
  • cleanliness
    Tranquil outdoor pool creates a shaded sanctuary amid Cape Cod attractions and ocean breezes.
$129 nightly
The price is $148
Oct 28 - Oct 29
Total with taxes and fees
A Beach Breeze Inn
A swimming pool with lounge chairs and a building in the background.

10. Handkerchief Shoals Inn

Handkerchief Shoals Inn
2.5 star property
South Harwich
8.6 out of 10, Excellent, (240 reviews)
$178 nightly
The price is $204
Oct 28 - Oct 29
Total with taxes and fees
Handkerchief Shoals 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.
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Choose what matters most at hotels with a pool in Chatham

Breakfast included
4 stars

Top Chatham Hotel Reviews

Cape Sands Inn

Cape Sands Inn

8/10 Good
"Great location, everything was near by. You get what you paid for. It served its purpose, I felt safe as a solo traveler."
Eva 2-night trip
Posted 3 hours ago
Cape Sands Inn

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 $129 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.
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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