Find Hotels with a Pool in Chatham, MA
Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member PricesLearn about One Key
Be pickySearch almost a million properties worldwide
Check availability on Chatham Hotels with a Pool
Tonight
Aug 13 - Aug 14Tomorrow
Aug 14 - Aug 15This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23Our top choices for Chatham hotels with a pool
1. Greyfinch Chatham Inn
Greyfinch Chatham InnChatham
- 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
2. Chatham Seafarer Inn
Chatham Seafarer InnChatham
- 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
3. Chatham Wayside Inn
Chatham Wayside InnChatham
- 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
4. Pleasant Bay Village Resort
Pleasant Bay Village ResortChatham
- 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
5. Chatham Bars Inn
Chatham Bars InnChatham
- 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
6. Olde Tavern Motel And Inn
Olde Tavern Motel And InnOrleans
- 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
7. Wequassett Resort and Golf Club
Wequassett Resort and Golf ClubHarwich
- 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
8. Holiday Hill Inn & Suites
Holiday Hill Inn & SuitesDennis 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
View all properties
Top Chatham Hotel Reviews
Holiday Hill Inn & Suites
8/10 Good
"Nice hotel"
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."
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"
Uncommoner Hotel by Reverie Boutique Collection
8/10 Good
"Nice place not right in the middle of 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!"
All Seasons Resort, Trademark Collection by Wyndham
10/10 Excellent
"Cleaned and everything is there"
Chatham Wayside Inn
10/10 Excellent
"Spacious room, lovely pool, clean, great location (heart of downtown)"
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."
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."
Frequently asked questions
Explore a world of travel with Expedia
- Hotels with Fireplaces in Chatham
- Hotels with Balconies in South Yarmouth
- Hotels with Suites in West Yarmouth
- Hotels on the Lake in Cape Cod
- Hotels with Balconies in Cape Cod
- Historic Hotels in South Yarmouth
- Hotels with Air Conditioning in Cape Cod
- Hotels with Bars in Chatham
- Hotels with smoking rooms in Yarmouth Port
- Oceanfront Hotels in Cape Cod
- Romantic Hotels in South Yarmouth
- Beach Hotels in Chatham
- Luxury Hotels in Chatham
- Hotels with a View in Cape Cod
- Resorts & Hotels with Spas in Hyannis
- Family Hotels in West Yarmouth
- Hotels with Free Wifi in Cape Cod
- Oceanfront Hotels in Yarmouth Port
- Cheap Hotels in Cape Cod
- Hotels with Connecting Rooms in South Yarmouth
- Hotels with Connecting Rooms in Hyannis
- Family Hotels in Cape Cod
- Hotels with Air Conditioning in South Yarmouth
- Historic Hotels in Chatham
- Adults Only Resorts & in Chatham
- Hotels with Laundry Facilities in Hyannis
- Hotel Wedding Venues Hotels in West Yarmouth
- All-Inclusive Resorts in Yarmouth Port
- Cheap Hotels in South Yarmouth
- Gay friendly Hotels in Cape Cod
- Hotels with Hot Tubs in West Yarmouth
- Hotels with Tennis Courts in Chatham
- Hotels with smoking rooms in Chatham
- All-Inclusive Resorts in Cape Cod
- Beach Hotels in Cape Cod
- All-Inclusive Resorts in Chatham
- Hotels with a Pool in West Yarmouth
- Oceanfront Hotels in Dennis Port
- Hotels with an Outdoor Pool in West Yarmouth
- Business Hotels in Cape Cod
- Hotels with Free Wifi in Dennis Port
- Family Hotels in Chatham
- Hotels with smoking rooms in West Yarmouth
- Casino Hotels in Chatham
- Fishing Resorts & in Cape Cod
- Hotels with Hot Tubs in Chatham
- Golf Hotels in West Yarmouth
- Hotels with Childcare in Cape Cod
- Hotels with Fireplaces in Cape Cod
- Luxury Hotels in South Yarmouth
- Hotels with Laundry Facilities in Cape Cod
- Waterpark Hotels in Hyannis
- Hotels with Free Airport Shuttle in Cape Cod
- Hotels with Restaurants in Cape Cod
- Hotels with Laundry Facilities in Chatham
- Cheap Hotels in Chatham
- Waterpark Hotels in West Yarmouth
- Hotels with smoking rooms in Cape Cod
- Romantic Hotels in Hyannis
- Gay friendly Hotels in Yarmouth Port
- Hotels with a Swim-up Bar in Hyannis
- Hotels with Kitchenettes in Chatham
- Luxury Hotels in Yarmouth Port
- Hotels with Kitchenettes in Hyannis
- Hotels with Hot Tubs in South Yarmouth
- Hotels & Resorts for Couples in South Yarmouth
- Hotels with a Lazy River in Cape Cod
- Hotels with Tennis Courts in Cape Cod
- All-Inclusive Resorts in West Yarmouth
- Extended Stay Hotels in Chatham
- Hotels with Free Parking in Cape Cod
- Hotels with Waterslides in Cape Cod
- Waterpark Hotels in Chatham
- Oceanfront Hotels in Chatham
- Hotels with Bars in Yarmouth Port
- Beach Hotels in West Yarmouth
- Hotel Wedding Venues Hotels in Chatham
- Hotels with Bars in Hyannis
- Hotels with smoking rooms in Hyannis
- Extended Stay Hotels in West Yarmouth
- Hotels with smoking rooms in South Yarmouth
- Hotels with Connecting Rooms in Cape Cod
- Pet-Friendly Hotels in Chatham
- Family Hotels in Yarmouth Port
- Hotels with Early Check-in in Cape Cod
- Hotels with Laundry Facilities in West Yarmouth
- Hotels with an Indoor Pool in Chatham
- Historic Hotels in Cape Cod
- Winery Hotels in Cape Cod
- Hotels with Kitchenettes in West Yarmouth
- Hotels with Air Conditioning in Chatham
- Resorts & Hotels with Spas in West Yarmouth
- Romantic Hotels in Chatham
- Hotels with Free Breakfast in West Yarmouth
- Pet-Friendly Hotels in Cape Cod
- Golf Hotels in South Yarmouth
- Hotels with Room Service in Cape Cod
- Adults Only Resorts & in Yarmouth Port
- Quiet Resorts & in Cape Cod
- Luxury Hotels in West Yarmouth