Title: Book the Best Hotels with POOL in Madison in 2025 | Expedia.ca [Madison Travel Guide](https://expedia.ca/Madison.dx8791)[Hotels in Madison](https://expedia.ca/Madison-Hotels.d8791.Travel-Guide-Hotels)[Vacation Rentals in Madison](https://expedia.ca/Madison-Vacation-Rentals.d8791.Travel-Guide-VacationRentals)[Flights to Madison](https://expedia.ca/Cheap-Flights-To-Madison.d8791.Travel-Guide-Flights)[Madison Car Rentals](https://expedia.ca/Car-Rentals-In-Madison.d8791.Car-Rental-Guide)[Madison Vacation Packages](https://expedia.ca/Madison.d8791.Destination-Travel-Guides) ![A Connecticut home in autumn surrounded by colorful foliage.](https://images.trvl-media.com/place/8791/579db867-4a05-43b0-acaa-e0e5981d4123.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Madison, CT - ![](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 Madison Hotels with a Pool Tonight [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-11-23&endDate=2025-11-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-11-24&endDate=2025-11-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Madison Hotels with a Pool ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w1536h1018x0y0-00be5d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/20551fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/w3834h2560x6y0-25f93ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/708b4a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Niantic - New London/Mystic Area Niantic 9.0/10 Wonderful (437) "Very nice property and staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George CA $130 CA $150 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/1345db22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/4e8534b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Harbor View Terrace Suite | View from room](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/a8d80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn Greenport 8.8/10 Excellent (535) "Amazing property, rooms, and staff. Book a room with a balcony for amazing views!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $147 CA $237 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/94835d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/58473cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Bedroom, Patio](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f43c4f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Fork Cottages & RV Resort Greenport 9.4/10 Exceptional (6) "great place to stay, clean and quiet....loved it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darlin CA $247 CA $283 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/ec5a48cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/d045ec83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/cb3d49ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG Southington 8.6/10 Excellent (1154) "Room was clean, hotel was quiet in a good location, continental breakfast had good variety. Would definitely stay here again. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Angela CA $134 CA $154 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/w1703h1271x0y0-b305e0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/33420ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/e12904c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Cheshire - Southington by IHG Southington 8.2/10 Very good (1002) "Great stay can’t complain" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $162 CA $187 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/ecdb1729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/w531h370x4y0-37170d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/936ec60f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Plainville Plainville 8.6/10 Excellent (907) "Yes, the room was clean. Staff was very nice and we look forward to our next stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liza Marie CA $123 CA $141 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/4c9856c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/f76cf168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, beach views ](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/55b708b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sound View Greenport Greenport 8.6/10 Excellent (593) "Staff was amazing , room clean view phenomenal " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $226 CA $327 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/84e6e761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/657809e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/5ef2aedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/b3db2b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New England Inn & Suites Berlin 8.6/10 Excellent (1008) "great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $124 CA $143 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) ![Indoor pool, open 8:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/ad1ecac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/53845527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/8a5f6b59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, free cribs/infant beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/7000000/6480000/6476900/6476838/e74b837a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Southington, CT Southington 9.2/10 Wonderful (1007) "Great staff, clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $179 CA $206 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Southington.h6476838.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/a45c48e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily breakfast](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/4a7d934c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Accessible, Bathtub | Living area](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/5717ad56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Orange New Haven Orange 9.2/10 Wonderful (1006) "The room was clean the staff was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $157 CA $180 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.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=2025-12-07&endDate=2025-12-08®ionId=8791&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_8791) ## Top Madison Hotel Reviews ![Clarion Inn](https://images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "Clean room" [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](https://images.trvl-media.com/lodging/1000000/10000/1300/1241/dbc425d9_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 10/10 Excellent "clean, quiet. fulfilled my expectations " [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "The housekeepers did an excellent job. Also, front desk staff was very warm snd hospitable. Breakfast was cooked to order and invluded fresh pineapple and blueberries. The location was peaceful, away from the city." [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "Excellent check-in staff." [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](https://images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "Everything was great!!" [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "The room was very clean, bed was comfy, and the sounds of the water outside were lovely. I did arrive very late and all parking spots were taken which was sort of inconvenient as it is a bit of a walk to park by other rooms. Check in process was super smooth." [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "room was clean and service was excellant. Front desk staff great and very helpful" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Awesome " [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Madison? > [Madison Beach Hotel](https://www.expedia.ca/Madison-Hotels-Madison-Beach-Hotel.h1209378.Hotel-Information): Provides a snack bar/deli, a seasonal outdoor pool, and buffet. [New Haven Hotel](https://www.expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information): Offers a private beach, a seasonal outdoor pool, and 2 bars. [Holiday Inn Express Southington by IHG](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information): Provides full, a pool, and free self parking. [Cambria Hotel New Haven University Area](https://www.expedia.ca/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information): Features a snack bar/deli, an indoor pool, and free self parking. [Sound View Greenport](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information): Offers buffet, an indoor pool, and complimentary wired internet access. ### What is there to see and do in Madison? > Make a point to visit attractions like Hammonasset Beach and RJ Julia Booksellers. During your stay, check out sights such as Hammonasset Beach State Park, Allis-Bushnell House and Museum, and Meigs Point Nature Center. Take in the natural beauty of Madison with the beaches. ### When is the best time to book a hotel with a pool in Madison? > You may want to consider a place to stay with an outdoor swimming pool if you will be visiting Madison in the hottest months of July, August, or June when the average temp is 70°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temperature is 35°F. ### What's the best way to travel around Madison? > Knowing the transportation options in and around Madison can help you enjoy the area beyond your hotel pool. If you want to explore the larger area, hop aboard a train at Madison Station. 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