Title: Book the Best Hotels with POOL in Madison in 2026 | 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) ![](https://images.trvl-media.com/place/8791/579db867-4a05-43b0-acaa-e0e5981d4123.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2026-01-15&endDate=2026-01-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Reception](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/3bed0df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/d736f3ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchenette (Shower Only;with Sofabed) | Private kitchenette](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/23a00626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Niantic - New London/Mystic Area [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) Niantic 9.0/10 Wonderful (458 reviews) "The room was clean and the staff was helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $121 CA $139 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.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/fce9c835.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) ![](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/9672e16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Cheshire - Southington by IHG [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) Southington 8.4/10 Very good (1,000 reviews) "Pool was nice, breakfast was very good. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $137 CA $158 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/83c7bce7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/8a4a605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/ac1b5094.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 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information) Greenport 8.6/10 Excellent (606 reviews) "Nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mateusz CA $186 CA $252 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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/44000000/43540000/43532300/43532300/2c9cc7e9.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) ![Lobby lounge](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/717b3774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Harbor Front Inn [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) Greenport 8.8/10 Excellent (562 reviews) "Everything was Great Immaculate hotel very good location sraff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) latoya CA $164 CA $227 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/2f044af4.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) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/d9e2e7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/94c389ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New England Inn & Suites [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) Berlin 8.6/10 Excellent (1,017 reviews) "Excellent Very warm staff Beds are very comfortable Coffee machine is such a great idea Breakfast was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $121 CA $139 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.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) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/06fc08bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, individually furnished](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/3627bf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/da165588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Southington by IHG [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) Southington 8.6/10 Excellent (1,199 reviews) "Clean comfortable room, friendly staff, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan CA $119 CA $137 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/15d5ef38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/adaca4d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/1b9db1ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/ad096b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Wallingford/Meriden [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-WallingfordMeriden.h11440147.Hotel-Information) Wallingford 8.8/10 Excellent (1,000 reviews) "The staff and the hotel were amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $159 CA $183 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-WallingfordMeriden.h11440147.Hotel-Information) ![Indoor pool, open 9:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/604acd23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/be26a516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Old Saybrook - Westbrook [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) Old Saybrook 7.8/10 Good (1,002 reviews) "The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virginia CA $124 CA $143 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f9bec315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free cribs/infant beds, rollaway beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d1788901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clinton Motel [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) Clinton 8.6/10 Excellent (300 reviews) "Is good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $108 CA $125 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/8957afe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/fce2d4ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; ocean views](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/719b8aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saybrook Point Resort & Marina [](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) Old Saybrook Center 9.6/10 Exceptional (1,003 reviews) "Wonderful stay in a beautiful setting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $376 CA $468 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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=2026-01-29&endDate=2026-01-30®ionId=8791&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Madison Hotel Reviews ![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg) ### Water's Edge Resort & Spa 10/10 Excellent "Great room and staff" [](https://expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.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 "Beautifully appointed, great staff, comfortable beds and hearty breakfast!! We’d have no problem recommending this hotel to family and friends. 😁" [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.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 "yes" [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.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 "The staff was kind and courteous from the moment we arrived. Our room was very clean and our breakfast was good as well. We would most likely return if in the area in the future." [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.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 "Good" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Inn at Middletown](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540_y.jpg) ### Inn at Middletown 10/10 Excellent "Staff was wonderful, lovely hotel" [](https://expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.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 "A" [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Motel 6 Niantic, CT - New London](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039681/0c062ad1_y.jpg) ### Motel 6 Niantic, CT - New London 10/10 Excellent "Great !!" [](https://expedia.ca/Niantic-Hotels-Motel-6-Niantic.h1039681.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Madison? ### What is there to see and do in Madison? ### When is the best time to book a hotel with a pool in Madison? ### What's the best way to travel around Madison? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Guilford ](https://www.expedia.ca/4Star-Guilford-Hotels.s40-0-d183062.Travel-Guide-Filter-Hotels) - [Hotels near Chamard Vineyards ](https://www.expedia.ca/Chamard-Vineyards-Hotels.0-l6309929-0.Travel-Guide-Filter-Hotels) - [B&B in Chester ](https://www.expedia.ca/Chester-Bed-And-Breakfast.d183058-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Chester ](https://www.expedia.ca/Chester-Chalets.d183058-aaChalets.Travel-Guide-Accommodation) - [Country Houses in Chester ](https://www.expedia.ca/Chester-Country-House.d183058-aaCountryHouse.Travel-Guide-Accommodation) - 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