Title: The Best Chatham Hotels with Pools from $92 - Hotels with indoor pools in Chatham, MA | 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 [Mar 17 - Mar 18](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-03-17&endDate=2026-03-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 18 - Mar 19](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-03-18&endDate=2026-03-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=10743&startDate=2026-03-27&endDate=2026-03-29&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/2000000/1520000/1517300/1517204/97707902.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) ![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) ### Chatham Wayside Inn [](https://www.expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) Chatham 9.2/10 Wonderful (642 reviews) - Dive into seaside bliss at this Cape Cod hotel with a sun-soaked seasonal pool and relaxing loungers for perfect summer days. $157 nightly $180 total Mar 22 - Mar 23 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/3000000/2040000/2034800/2034734/60e08d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/d50e3e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/7fb17e84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Multiple Beds | Iron/ironing board, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/f938f5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Seafarer Inn [](https://www.expedia.com/Chatham-Hotels-Chatham-Seafarer-Inn.h2034734.Hotel-Information) Chatham 9.0/10 Wonderful (319 reviews) - Splash into serenity at the seasonal outdoor pool, where relaxation flows from morning until evening. $154 nightly $176 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Chatham-Hotels-Chatham-Seafarer-Inn.h2034734.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/8a15db85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, soundproofing](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/be663734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/e981387d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7fbb17d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greyfinch Chatham Inn [](https://www.expedia.com/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.Hotel-Information) Chatham 8.8/10 Excellent (254 reviews) - Escape to the Cape Cod oasis with a seasonal outdoor pool, free bicycles, and modern comforts just steps from local beaches. $193 nightly $221 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.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) ![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/efc614b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/13fe4b58.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 (813 reviews) - Dive into beachside bliss with a private shoreline, seasonal pool, and chauffeured beach shuttle for ultimate seaside luxury. $368 nightly $421 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71780000/71778600/71778590/85e6fd53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71780000/71778600/71778590/34f69a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71780000/71778600/71778590/w1597h1181x0y19-161a0f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71780000/71778600/71778590/fd7b89bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome! [](https://www.expedia.com/Chatham-Hotels-Luxury-9-BR-Home-With-Heated-Pool-In-Downtown-Chatham.h71778590.Hotel-Information) Chatham 10/10 Exceptional (40 reviews) $2,538 nightly $2,905 total Apr 10 - Apr 11 Total with taxes and fees [](https://www.expedia.com/Chatham-Hotels-Luxury-9-BR-Home-With-Heated-Pool-In-Downtown-Chatham.h71778590.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 (673 reviews) - Immerse in a refreshing summer retreat at this clean, seasonal pool oasis with beach-themed charm. $80 nightly $92 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/South-Yarmouth-Hotels-The-Escape-Inn.h6697712.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/963d562c.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) ### Bayside Resort Hotel [](https://www.expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) West Yarmouth 8.8/10 Excellent (1,551 reviews) - Float between two pools and bask in poolside bliss at this hotel with poolside bars and sunbathing spots. $123 nightly $141 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42420000/42411100/42411054/4faa774e.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) ![Fitness facility](https://images.trvl-media.com/lodging/43000000/42420000/42411100/42411054/cabfb3dc.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 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/South-Yarmouth-Hotels-Private-Cozy-Room-With-Resort-Amenities-And-Prime-Location.h42411054.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/77000000/76660000/76659000/76658936/cfb88979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76660000/76659000/76658936/300b7b42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76660000/76659000/76658936/2b595239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76660000/76659000/76658936/ffb11d43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🐚The Bay Cottage on Thumpertown Beach [](https://www.expedia.com/Eastham-Hotels-The-Bay-Cottage-On-Thumpertown-Beach.h76658936.Hotel-Information) Eastham 9.8/10 Exceptional (11 reviews) - Indoor pool and beachfront access in Cape Cod cottage offer relaxing escape near Thumpertown Beach and trails. $340 nightly $389 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Eastham-Hotels-The-Bay-Cottage-On-Thumpertown-Beach.h76658936.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/28000000/27440000/27432300/27432287/7fd5717b.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) ### "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 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/South-Yarmouth-Hotels-Awesome-Vacation-While-Staying-At-HomeAway-From-Home.h27432287.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=2026-03-31&endDate=2026-04-01®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 ## Top Chatham Hotel Reviews ![Cape Sands Inn](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/3bffd99c_y.jpg) ### Cape Sands Inn 6/10 Okay "Stay was ok- room was clean. The rooms do NOT have microwaves. We pick here because of the indoor pool and hot tub- however they close them as it it off season. " [](https://expedia.com/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.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 "The room was very comfortable. The bathroom was clean and the shower was really nice. The beds were so comfortable, too." [](https://expedia.com/Hyannis-Hotels-Holiday-Inn-Hyannis-By-IHG.h12477.Hotel-Information) ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/30f6a06a_y.jpg) ### Margaritaville Resort Cape Cod 10/10 Excellent "Beautiful place" [](https://expedia.com/Hyannis-Hotels-Cape-Codder-Resort-And-Spa.h12897.Hotel-Information) ![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/783b5af0_y.jpg) ### Bayside Resort Hotel 4/10 Poor "The cost for this place was over priced for the accommodations. Breakfast was nothing to talk about the whirlpool was load when draining and could here other filling theirs." [](https://expedia.com/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.Hotel-Information) ![Hyannis Plaza Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07_y.jpg) ### Hyannis Plaza Hotel 10/10 Excellent "Love this place " [](https://expedia.com/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information) ![Comfort Inn Hyannis - Cape Cod](https://images.trvl-media.com/lodging/2000000/1250000/1240500/1240460/b37d6e5b_y.jpg) ### Comfort Inn Hyannis - Cape Cod 8/10 Good "Good price" [](https://expedia.com/Hyannis-Hotels-Comfort-Inn.h1240460.Hotel-Information) ![Chatham Bars Inn](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/13fe4b58_y.jpg) ### Chatham Bars Inn 10/10 Excellent "Very nice room" [](https://expedia.com/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information) ![Anchor In Distinctive Waterfront Lodging](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/87d9418f_y.jpg) ### Anchor In Distinctive Waterfront Lodging 8/10 Good "Marry was great Room outdated and small" [](https://expedia.com/Hyannis-Hotels-Anchor-In-Distinctive-Waterfront-Lodging.h7640889.Hotel-Information) ![Chatham Wayside Inn](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002_y.jpg) ### Chatham Wayside Inn 2/10 Terrible "We booked the Hotel, called to check on the room as there was a Power outage in the area due to snow. We were told on the phone the room was ready. We arrived, went to check in. The women a reception informed us "You know we have no electricity, hot water, all facilities were closed. They were were willing to check us in, noting that there are only lights in the hallways. How about close the Hotel and halt booking? Terrible Managment." [](https://expedia.com/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.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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