Title: Book the Best Hotels with POOL in Chatham in 2025 | Expedia.ca [Chatham Travel Guide](https://expedia.ca/Chatham.dx10743)[Hotels in Chatham](https://expedia.ca/Chatham-Hotels.d10743.Travel-Guide-Hotels)[Vacation Rentals in Chatham](https://expedia.ca/Chatham-Vacation-Rentals.d10743.Travel-Guide-VacationRentals)[Flights to Chatham](https://expedia.ca/Cheap-Flights-To-Chatham.d10743.Travel-Guide-Flights)[Chatham Car Rentals](https://expedia.ca/Car-Rentals-In-Chatham.d10743.Car-Rental-Guide)[Chatham Vacation Packages](https://expedia.ca/Chatham.d10743.Destination-Travel-Guides) ![Chatham featuring a windmill, general coastal views and wild flowers](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105460-Chatham.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Chatham, MA ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](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 [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=10743&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chatham Hotels with a Pool ![Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/59358146.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) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/1adc0002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1520000/1517300/1517204/e74c9a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Wayside Inn Chatham 9.2/10 Wonderful (580) "Great hotel, great locatiion" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $213 CA $299 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/7cf38365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/8000000/7470000/7461700/7461681/94cdbe08.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/8000000/7470000/7461700/7461681/550a87c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greyfinch Chatham Inn Chatham 8.8/10 Excellent (252) "Wonderful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $200 CA $277 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Highlander-Village-Inn.h7461681.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) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/6317bcd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/bc33c61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/3000000/2040000/2034800/2034734/80bc5926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Seafarer Inn Chatham 9.0/10 Wonderful (318) "Lovely place to stay. The rooms were comfortable, beds very nice and the staff was great. A charming place to stay" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Virginia CA $216 CA $247 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Seafarer-Inn.h2034734.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/0e2de95d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/07d625ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Ocean View (Cottage) | View from room](https://images.trvl-media.com/lodging/1000000/20000/19200/19139/63585c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chatham Bars Inn Chatham 9.2/10 Wonderful (792) "Excellent experience all around Gorgeous location and beautiful hotel Lively lobby " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Montana CA $529 CA $636 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.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) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6700000/6697800/6697712/9440495d.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) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6700000/6697800/6697712/32aabc06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Escape Inn Bass River 9.4/10 Exceptional (639) "a great clean room you can tell the owners take pride in the Escape inn . we enjoyed our stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $112 CA $129 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/South-Yarmouth-Hotels-The-Escape-Inn.h6697712.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/81ee3965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/36e3cf8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/438fdc4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1180000/1173600/1173572/2c3e374d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wellfleet Motel and Lodge Wellfleet 9.4/10 Exceptional (1010) "The room was so nice and breakfast was delicious " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele CA $124 CA $142 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wellfleet-Hotels-Wellfleet-Motel-And-Lodge.h1173572.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/aa954682.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/d3887aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/efa49ff6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1340000/1330200/1330174/3bffd99c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cape Sands Inn West Yarmouth 8.2/10 Very good (1009) "I love this hotel clean good up keep " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerome CA $107 CA $123 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/West-Yarmouth-Hotels-Cape-Sands-Inn.h1330174.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2740000/2730300/2730253/979155cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2740000/2730300/2730253/68ce2f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/3000000/2740000/2730300/2730253/71bfa777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2740000/2730300/2730253/583652e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### All Seasons Resort, Trademark Collection by Wyndham Bass River 8.4/10 Very good (293) "Great for kids" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $145 CA $185 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/South-Yarmouth-Hotels-All-Seasons-Resort.h2730253.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/786ccd3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/ef69e045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/f7fc1d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Plaza Suite](https://images.trvl-media.com/lodging/2000000/1120000/1119300/1119277/34fe26da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyannis Plaza Hotel Hyannis 7.0/10 Good (942) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mirza CA $86 CA $113 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Hyannis-Hotels-Hyannis-Plaza-Hotel.h1119277.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/85f07916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/557f1a26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/a80381e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, pub, pub](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/37259fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Resort Hotel West Yarmouth 8.8/10 Excellent (1521) "Great spot for families, indoor pool was wonderful and arcade, fire pit and good breakfast options." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaitlyn CA $129 CA $163 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/West-Yarmouth-Hotels-Bayside-Resort-Hotel.h896697.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.ca/Hotel-Search?startDate=2025-11-11&endDate=2025-11-12®ionId=10743&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chatham Hotel Reviews ## Frequently asked questions ### What are some accommodations with pools in Chatham? > [Chatham Wayside Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Wayside-Inn.h1517204.Hotel-Information): Hotel, 11-minute walk from Cape Cod Beaches. Features daily, a seasonal outdoor pool, and free self parking. [Chatham Bars Inn](https://www.expedia.ca/Chatham-Hotels-Chatham-Bars-Inn.h19139.Hotel-Information): Resort, 4-minute walk from Cape Cod Beaches. Offers a private beach, a seasonal outdoor pool, and a full-service spa. [The Chatham Motel](https://www.expedia.ca/Chatham-Hotels-The-Chatham-Motel.h4616460.Hotel-Information): Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. ### What is there to see and do in Chatham? > Spend some time experiencing the great outdoors at Chatham Lighthouse Beach and Ridgevale Beach. During your stay, check out sights such as Chatham Fish Pier, Chatham Lighthouse, and Cape Cod Beaches. Visitors to Chatham speak highly of the natural attractions, including the beautiful beaches. ### When is the best time to book a hotel with a pool in Chatham? > Taking into account the local weather in Chatham is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches. ## Explore a world of travel with Expedia - Lodging - Packages - Cars - More ways to book - [Adults Only Resorts & in Boston](https://www.expedia.ca/Boston-Hotels-Adults-Only-Resorts.0-0-d178239-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Business Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Business-Hotel.0-0-d178239-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Boston](https://www.expedia.ca/Boston-Hotels-Couples-Resorts-Hotels.0-0-d178239-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Golf-Hotel.0-0-d178239-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Boston](https://www.expedia.ca/Boston-Hotels-Green-Sustainable.0-0-d178239-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Boston](https://www.expedia.ca/Boston-Hotels-Hotel-With-Wifi.0-0-d178239-tHotelwithwifi.Travel-Guide-Filter-Hotels) - 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