Title: The Best Hotels with a Pool in Chatham from $92 in 2026 | Expedia.com [Chatham Travel Guide](https://expedia.com/Chatham.dx10743)[Hotels in Chatham](https://expedia.com/Chatham-Hotels.d10743.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.com/Chatham-Vacation-Rentals.d10743.Travel-Guide-VacationRentals)[Flights to Chatham](https://expedia.com/Cheap-Flights-To-Chatham.d10743.Travel-Guide-Flights)[Things to do in Chatham](https://expedia.com/Things-To-Do-In-Chatham.d10743.Travel-Guide-Activities)[Car Rentals in Chatham](https://expedia.com/Car-Rentals-In-Chatham.d10743.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.com/Chatham.d10743.Destination-Travel-Guides) ![Chatham showing a windmill, wildflowers and general coastal views](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/10743/d3f8b886-55a4-46b3-afab-39fd14b1b518.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chatham Hotels with a Pool Tonight [Feb 27 - Feb 28](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-02-27&endDate=2026-02-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 28 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-02-28&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chatham hotels with a pool ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/0dedd969.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/471fd6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/97707902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn [](https://www.expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) Chatham 9.2/10 Wonderful (635 reviews) - Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days. $156 nightly $179 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/efc614b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, aromatherapy](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5695h3900x5y0-3649fa2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/c3fa2de8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Bars Inn [](https://www.expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) Chatham 9.2/10 Wonderful (812 reviews) - Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury. $364 nightly $417 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/28000000/27440000/27432300/27432287/0e03da8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27440000/27432300/27432287/ed418c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27440000/27432300/27432287/2eb0f5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/28000000/27440000/27432300/27432287/56a3eda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Awesome Vacation while staying at "HomeAway" from Home" [](https://www.expedia.com/South-Yarmouth-Hotels-Awesome-Vacation-While-Staying-At-HomeAway-From-Home.h27432287.Hotel-Information) Bass River 8.2/10 Very Good (81 reviews) $145 nightly $166 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/South-Yarmouth-Hotels-Awesome-Vacation-While-Staying-At-HomeAway-From-Home.h27432287.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/43000000/42420000/42411100/42411054/005f4d84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/43000000/42420000/42411100/42411054/cabfb3dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/43000000/42420000/42411100/42411054/f2f65438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42420000/42411100/42411054/26f13732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All Seasons Resort [](https://www.expedia.com/South-Yarmouth-Hotels-Private-Cozy-Room-With-Resort-Amenities-And-Prime-Location.h42411054.Hotel-Information) Bass River 9.0/10 Wonderful (57 reviews) $113 nightly $129 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/South-Yarmouth-Hotels-Private-Cozy-Room-With-Resort-Amenities-And-Prime-Location.h42411054.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6700000/6697800/6697712/5bdfdac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6700000/6697800/6697712/366fdd27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6700000/6697800/6697712/32aabc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6700000/6697800/6697712/b61b6541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Escape Inn [](https://www.expedia.com/South-Yarmouth-Hotels-The-Escape-Inn.h6697712.Hotel-Information) Bass River 9.4/10 Exceptional (672 reviews) - Immerse in a refreshing summer retreat at this clean, seasonal pool oasis with beach-themed charm. $80 nightly $92 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/South-Yarmouth-Hotels-The-Escape-Inn.h6697712.Hotel-Information) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/dda22c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/d6513126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/46a3fe6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/96000000/95140000/95132700/95132664/3ddb0693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA [](https://www.expedia.com/Brewster-Hotels-Ocean-Edge-Cape-Cod-2-Bed-2-Bath.h95132664.Hotel-Information) Brewster 10/10 Exceptional (42 reviews) - Aquatic paradise awaits with indoor/outdoor pools and hot tub at this Cape Cod retreat by a golf course. $319 nightly $365 total Feb 28 - Mar 1 Total with taxes and fees [](https://www.expedia.com/Brewster-Hotels-Ocean-Edge-Cape-Cod-2-Bed-2-Bath.h95132664.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/39000000/38360000/38357900/38357891/8538a76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38360000/38357900/38357891/1f21d7a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38360000/38357900/38357891/b38fce29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/39000000/38360000/38357900/38357891/bc568ce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aiden by Best Western Cape Cod - West Yarmouth [](https://www.expedia.com/West-Yarmouth-Hotels-Aiden-By-Best-Western-Cape-Point.h38357891.Hotel-Information) West Yarmouth 8.0/10 Very Good (1,002 reviews) - Swim in serenity at a beachside oasis with both indoor and seasonal outdoor pools. $82 nightly $94 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/West-Yarmouth-Hotels-Aiden-By-Best-Western-Cape-Point.h38357891.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/783b5af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/146eb322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/b70d15f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Bay View | Premium bedding, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/d77a27ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Resort Hotel [](https://www.expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) West Yarmouth 8.8/10 Excellent (1,559 reviews) - Float between two pools and bask in poolside bliss at this hotel with poolside bars and sunbathing spots. $104 nightly $118 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/3fdd0247.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/bfb8a032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Queen Beds Harborview Suite | Living area | 55-inch Smart TV with cable channels, Netflix, Hulu](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/c85afb09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/87d9418f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchor In Distinctive Waterfront Lodging [](https://www.expedia.com/Hyannis-Hotels-Anchor-In-Distinctive-Waterfront-Lodging.h7640889.Hotel-Information) Hyannis 9.4/10 Exceptional (1,000 reviews) - Plunge into seaside splendor at this waterfront hotel's seasonal outdoor pool offering harbor views and complimentary loungers. $143 nightly $164 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Hyannis-Hotels-Anchor-In-Distinctive-Waterfront-Lodging.h7640889.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/056f2544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/6ac8a051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Voyager Escape King Elite | Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/c366b6b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/490000/480800/480770/75730e05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Uncommoner Hotel by Reverie Boutique Collection [](https://www.expedia.com/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) West Yarmouth 9.2/10 Wonderful (115 reviews) - Renovated art deco hotel offers indoor and outdoor pools near Hyannis Harbor. $122 nightly $139 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/West-Yarmouth-Hotels-Tidewater-Inn.h480770.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-13&endDate=2026-03-14®ionId=10743&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Chatham Breakfast included 4 stars Hot tub 5 stars Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_10743) ## Top Chatham Hotel Reviews ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "Excellent ❤️❤️" [](https://expedia.com/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Edgewater Beach Resort, a VRI resort](https://images.trvl-media.com/lodging/2000000/1530000/1522300/1522228/5e9e9f5c_y.jpg) ### Edgewater Beach Resort, a VRI resort 10/10 Excellent "Clean rooms, excellent staff. " [](https://expedia.com/Dennis-Port-Hotels-Edgewater-Beach-Resort.h1522228.Hotel-Information) ![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916_y.jpg) ### Bayside Resort Hotel 10/10 Excellent "Clean and good size room, friendly staff, Expedia gold status perks, quiet on the 2nd floor, excellent complimentary breakfast" [](https://expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg) ### Chatham Wayside Inn 10/10 Excellent "Friendly staff, clean and spacious room, convenience of having a restaurant on site, and convenience of walking to all the stores and restaurants. " [](https://expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Hyannis Plaza Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg) ### Hyannis Plaza Hotel 10/10 Excellent "Good" [](https://expedia.com/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information) ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/w5700h3895x0y5-016d240d_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Beautiful property " [](https://expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![The Mansion at Ocean Edge](https://images.trvl-media.com/lodging/1000000/10000/8000/7948/5d8fbc52_y.jpg) ### The Mansion at Ocean Edge 10/10 Excellent "Didnt overlook beach." [](https://expedia.com/Brewster-Hotels-The-Mansion-At-Ocean-Edge.h7948.Hotel-Information) ![Fairfield Inn & Suites by Marriott Cape Cod Hyannis](https://images.trvl-media.com/lodging/1000000/10000/7700/7660/a974137b_y.jpg) ### Fairfield Inn & Suites by Marriott Cape Cod Hyannis 10/10 Excellent "The hotel is being remodeled, but the room is very clean. They even had gluten free options for breakfast, which made my little one super happy!" [](https://expedia.com/Hyannis-Hotels-Fairfield-Inn-Suites-By-Marriott-Cape-Cod-Hyannis.h7660.Hotel-Information) ![Holiday Inn Hyannis by IHG](https://images.trvl-media.com/lodging/1000000/20000/12500/12477/6128ed99_y.jpg) ### Holiday Inn Hyannis by IHG 10/10 Excellent "Check in was easy and the front desk person was wonderful. " [](https://expedia.com/Hyannis-Hotels-Holiday-Inn-Hyannis-By-IHG.h12477.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Chatham with outdoor pools? > For those seeking a more luxurious experience, [Chatham Bars Inn](https://www.expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) 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](https://www.expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information), 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? ### What are some of the best Chatham hotels with outdoor pools and scenic views? > 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? ### How can I save on a Chatham hotel with a pool with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Gallery Antonia ](https://www.expedia.com/Gallery-Antonia-Hotels.0-l553248621532666630-0.Travel-Guide-Filter-Hotels) - [Hotels near Monomoy Theatre ](https://www.expedia.com/Monomoy-Theatre-Hotels.0-l6286898-0.Travel-Guide-Filter-Hotels) - [Hotels near Chatham Railroad Museum ](https://www.expedia.com/Chatham-Railroad-Museum-Hotels.0-l6287125-0.Travel-Guide-Filter-Hotels) - [Hotels near Veterans Field ](https://www.expedia.com/Veterans-Field-Hotels.0-l6070219-0.Travel-Guide-Filter-Hotels) - [Hotels near Chatham Seaside Links ](https://www.expedia.com/Chatham-Seaside-Links-Hotels.0-l6286368-0.Travel-Guide-Filter-Hotels) - 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