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) ![](https://mediaim.expedia.com/destination/1/aec1da8b8b4af7badc0c68e92a6d88e8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Madison, CT from CA $125 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Madison Hotels with a Pool Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-10-07&endDate=2025-10-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=8791&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Madison Hotels with a Pool ![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 self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/d45c604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clinton Motel Clinton 8.6/10 Excellent (280) "Great staff and clean rooms" CA $109 CA $125 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/fa5a1a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/ad990fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/0122d57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/7000000/6480000/6473500/6473437/988fd965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pridwin Hotel Shelter Island Heights 9.6/10 Exceptional (80) "The staff was amazing" CA $463 CA $582 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Shelter-Island-Heights-Hotels-The-Pridwin-Hotel.h6473437.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c3d8e2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/e78d099b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/c7d19019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Greenporter Hotel Greenport 9.2/10 Wonderful (260) "Staff was amazing and this hotel is in the perfect location " CA $186 CA $213 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information) ![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) ![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) ![Daily self-serve breakfast for a fee](https://images.trvl-media.com/lodging/10000000/9520000/9517100/9517042/c2934dcf.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) ### Best Western Niantic - New London/Mystic Area Niantic 9.0/10 Wonderful (390) "Nice clean hotel. " CA $129 CA $148 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Niantic-Hotels-Best-Western-Niantic-Inn.h9517042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/5c6281d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, body treatments](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/533d1f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/ccd49f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Water's Edge Resort & Spa Westbrook Center 8.8/10 Excellent (1004) "clean and quiet property, great views, amazing staff" CA $305 CA $375 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/92000000/91230000/91226500/91226444/c4055e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/92000000/91230000/91226500/91226444/3118ddf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed with Sofa bed, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/92000000/91230000/91226500/91226444/w4000h2663x0y0-497d73e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/92000000/91230000/91226500/91226444/86503aca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott New Haven Hamden Hamden 9.4/10 Exceptional (398) "Great hotel." CA $231 CA $266 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hamden-Hotels-Residence-Inn-By-Marriott-New-Haven-Hamden.h91226444.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/1f2f0ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/fcbc5aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/0faee1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton East Haven New Haven The Centre 9.6/10 Exceptional (400) "Very nice rooms and staff" CA $182 CA $210 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.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) ![Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/770255ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/65651fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/f7da52a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saybrook Point Resort & Marina Old Saybrook Center 9.4/10 Exceptional (1005) "Great place!! " CA $363 CA $452 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/c68b41ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/eff2fea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/4e71c540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/7000000/6750000/6747900/6747876/ec875b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Middletown Middletown 9.0/10 Wonderful (507) "Very nice property convenient to Wesleyan and Middletown" CA $245 CA $309 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Hartford-Hotels-Inn-At-Middletown.h6747876.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) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/ad096b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/19bd6a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/12000000/11450000/11440200/11440147/8a31f79b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Wallingford/Meriden Wallingford 9.0/10 Wonderful (1003) "Beautiful Hotel" CA $212 CA $244 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-WallingfordMeriden.h11440147.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=2025-10-21&endDate=2025-10-22®ionId=8791&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Madison Hotel Reviews ![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "Very neat and tidy, in and around the property. All basic necessities available. Good value for money. " [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Quality Inn Old Saybrook - Westbrook](//images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg) ### Quality Inn Old Saybrook - Westbrook 10/10 Excellent "We were there 1 night, so i didnt notice shops. But there was a good restaurant across the road." [](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](//images.trvl-media.com/lodging/1000000/10000/1300/1241/92ca5e77_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 8/10 Good "Under construction." [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ![Holiday Inn Express Southington by IHG](//images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "excellent hotel,room clean and excellent service." [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Clarion Inn](//images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "Nice property - the staff was very helpful and courteous. Not very fancy, but clean with comfortable beds and great pillows that did not just go flat the second you put your head on them!" [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](//images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "νονε" [](https://expedia.ca/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Sound View Greenport](//images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/b52e0fa4_y.jpg) ### Sound View Greenport 10/10 Excellent "Clean and beautiful view" [](https://expedia.ca/Greenport-Hotels-Sound-View-Greenport.h15273178.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): Offers full, a pool, and free self parking. [Omni New Haven Hotel at Yale](https://www.expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information): Features 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): Hotel located near Quinnipiac University. Offers buffet, an indoor pool, and complimentary wired internet access. [Red Roof Inn Meriden](https://www.expedia.ca/Hartford-Hotels-Red-Roof-Inn-Meriden.h2831.Hotel-Information): Features a private beach, a seasonal outdoor pool, and 2 bars. [Best Western Executive Hotel Of New Haven - West Haven](https://www.expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information): Features buffet, an indoor pool, and free self parking. ### 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, North Madison Shopping Center, and Allis-Bushnell House and Museum. 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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