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

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Chatham hotels with a pool

1. Greyfinch Chatham Inn

Greyfinch Chatham Inn
Chatham
  • Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches.
$256 nightly
$293 total
Sep 7 - Sep 8
Total with taxes and fees
Greyfinch Chatham Inn

2. Chatham Seafarer Inn

Chatham Seafarer Inn
Chatham
  • Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening.
$254 nightly
$290 total
Sep 17 - Sep 18
Total with taxes and fees
Chatham Seafarer Inn

3. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
  • Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days.
$394 nightly
$451 total
Aug 26 - Aug 27
Total with taxes and fees
Chatham Wayside Inn

4. Pleasant Bay Village Resort

Pleasant Bay Village Resort
Chatham
  • Splash into vacation bliss at this Cape Cod retreat with outdoor pool and soothing hot tub.
$290 nightly
$332 total
Sep 8 - Sep 9
Total with taxes and fees
Pleasant Bay Village Resort

5. Chatham Bars Inn

Chatham Bars Inn
Chatham
  • Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury.
$578 nightly
$662 total
Sep 14 - Sep 15
Total with taxes and fees
Chatham Bars Inn

6. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
Orleans
  • Soak in coastal charm at the seasonal outdoor pool surrounded by lush garden views at this beautifully renovated motel.
$135 nightly
$155 total
Sep 2 - Sep 3
Total with taxes and fees
Olde Tavern Motel And Inn

7. Handkerchief Shoals Inn

Handkerchief Shoals Inn
South Harwich
$178 nightly
$204 total
Sep 14 - Sep 15
Total with taxes and fees
Handkerchief Shoals Inn

8. The Villages at Ocean Edge

The Villages at Ocean Edge
Brewster
  • Dive into paradise with 7 amazing pools, each offering a different vibe for every vacation mood.
$195 nightly
$223 total
Sep 20 - Sep 21
Total with taxes and fees
The Villages at Ocean Edge

9. Skaket Beach Motel

Skaket Beach Motel
Orleans
  • Dive into relaxation at this coastal motel's seasonal outdoor pool, just steps from beautiful Skaket Beach and sunset views.
$140 nightly
$160 total
Sep 13 - Sep 14
Total with taxes and fees
Skaket Beach Motel

10. Holiday Hill Inn & Suites

Holiday Hill Inn & Suites
Dennis Port
  • Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.
$104 nightly
$119 total
Aug 31 - Sep 1
Total with taxes and fees
Holiday Hill Inn & Suites
View all properties

Choose what matters most at hotels with a pool in Chatham

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Chatham Hotel Reviews

Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"Clean room and great location"
Sara 3-night trip
Posted 1 hour ago
Greyfinch Chatham Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Our stay at Margaritaville was superb. The hotel was clean and the rooms were delightful. The staff was very friendly and helpful. Very family friendly."
Ellen 3-night trip
Posted 3 hours ago
Margaritaville Resort Cape Cod
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Clean rooms , friendly staff , delicious breakfast , indoor outdoor pools , our room was overlooking a lake, very quite , highly recommend"
Christine 2-night trip
Posted 1 day ago
Uncommoner Hotel by Reverie Boutique Collection
Queen Anne Inn

Queen Anne Inn

8/10 Good
"The staff was very helpful for suggesting places to eat and visit"
Douglas 3-night trip
Posted 2 days ago
Queen Anne Inn
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

8/10 Good
"The front desk staff were nice and friendly. The beds were comfortable. The lobbies were nice. The pools could have been a bit cleaner, the mini golf needs some attention, and the breakfast is okay (coffee terrible). Overall, was a good stay and we’d go back. Definitely not a resort tho."
Mindy 2-night trip
Posted 2 days ago
The Mariner Resort Cape Cod by The Red Collection
Chatham Wayside Inn

Chatham Wayside Inn

8/10 Good
"Great location, close to the famous Squire and the restaurant (Wild Goose Tavern) on-site was terrific and made the experience a positive one. Elena makes an awesome martini, and Bobby was a friendly welcoming personality. Ben was awesome during dinner. Hotel staff should take lessons from the restaurants customer service training. Front Desk team is as cold as Elena’s martinis. Never a greet or smile unless we initiated. Not very welcoming. Room was fine. Bathroom not fine. Never stood in a tub that creaked before. Cheap bath fitter tub/shower, hospital room bathroom feel. Bed was comfy. Small pool which served its purpose for a quick refreshing dip. Wound consider a return but definitely wound explore other options as well."
Richard 3-night trip
Posted 3 days ago
Chatham Wayside Inn
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"Thoroughly enjoyed our visit. Perfect weekend in a perfect location. The grounds were beautiful, staff attentive. Rooms were amazing and clean. Even the turn down service was top notch. I will definitely plan another stay!"
Courtney 2-night trip
Posted 11 days ago
Pleasant Bay Village Resort

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 $119 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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