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Find Hotels with a Pool in Chatham, MA

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Check availability on Chatham Hotels with a Pool

Tonight
Aug 13 - Aug 14
Tomorrow
Aug 14 - Aug 15
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

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 1 - Sep 2
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.
$289 nightly
$330 total
Sep 10 - Sep 11
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.
$434 nightly
$497 total
Aug 31 - Sep 1
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.
$293 nightly
$336 total
Sep 7 - Sep 8
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.
$727 nightly
$832 total
Sep 3 - Sep 4
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.
$138 nightly
$158 total
Sep 3 - Sep 4
Total with taxes and fees
Olde Tavern Motel And Inn

7. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • Swim through summer in a luxury cabana paradise with poolside bars and ocean breezes.
$503 nightly
$575 total
Sep 8 - Sep 9
Total with taxes and fees
Wequassett Resort and Golf Club

8. 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.
$106 nightly
$121 total
Sep 2 - Sep 3
Total with taxes and fees
Holiday Hill Inn & Suites

9. GuestLodge

GuestLodge
West Dennis
  • Refreshing pool oasis awaits at Cape Cod motel with aquatic fun just steps from beaches.
$72 nightly
$82 total
Aug 31 - Sep 1
Total with taxes and fees
GuestLodge

10. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
Orleans
  • Splash into refreshing luxury with a clean, spacious pool perfect for sunny Cape Cod afternoons.
$135 nightly
$155 total
Sep 1 - Sep 2
Total with taxes and fees
Rodeway Inn Orleans - Cape Cod
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

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

8/10 Good
"Nice hotel"
Salvatore 4-night trip
Posted less than an hour ago
Holiday Hill Inn & Suites
Freebird Motor Lodge by Reverie Boutique Collection

Freebird Motor Lodge by Reverie Boutique Collection

8/10 Good
"Lovely renovated property. Clean rooms and the cleaning staff was very lovely and helpful. Great location and close to Seagull Beach. Lots of parking space."
Chantal 3-night trip
Posted 2 hours ago
Freebird Motor Lodge by Reverie Boutique Collection
The Mariner Resort Cape Cod by The Red Collection

The Mariner Resort Cape Cod by The Red Collection

10/10 Excellent
"Had a great time, room was good and clean! Parking is great you can park close. Pools clean, everything else was well taken care of. Orlando is fantastic and he should get a raise. Love that guy"
Adie 3-night trip
Posted 3 hours ago
The Mariner Resort Cape Cod by The Red Collection
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"Nice place not right in the middle of Cape Cod"
Zac 2-night trip
Posted 6 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Beautifully renovated resort. We loved that the room keys were wrist bracelets, easy to keep track of. The room was clean, fun, nautical theme touches, and very comfortable bed. The pool and waterpark were super fun for kids, they also had a great arcade. We ate dinner at their restaurant Landshark, solid food, but the wait was extremely long. They did compensate us well with a free drink and dessert, which was much appreciated. The breakfast buffet was extra, but not too much, and also very good. The grounds had additional games such as cornhole, tetherball, and large chess. Music in the late afternoon in the courtyard was a nice touch. Highly recommend, will definitely be back!"
Lindsay 1-night trip
Posted 16 hours ago
Margaritaville Resort Cape Cod
All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

10/10 Excellent
"Cleaned and everything is there"
Andres 1-night trip
Posted 20 hours ago
All Seasons Resort, Trademark Collection by Wyndham
Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Spacious room, lovely pool, clean, great location (heart of downtown)"
jacquelyn 3-night trip
Posted 20 hours ago
Chatham Wayside Inn
Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"Will absolutely come back with our kids again. The continental breakfast was a great way to quickly fuel up the family before we departed to do activities versus wasting time finding food in the AM. The pools were both great and the kids loved the arcade."
Francis 2-night trip
Posted 20 hours ago
Bayside Resort Hotel
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"The property was nice and clean. Ideal for a short stay for our family. The staff was very friendly and responsive."
Tatyana 4-night trip
Posted 22 hours ago
Greyfinch Chatham 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 $82 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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