Title: Book the Best Hotels with POOL in Fairfield in 2026 | Expedia.ca [Fairfield Travel Guide](https://expedia.ca/Fairfield.dx8066)[Hotels in Fairfield](https://expedia.ca/Fairfield-Hotels.d8066.Travel-Guide-Hotels)[Vacation Rentals in Fairfield](https://expedia.ca/Fairfield-Vacation-Rentals.d8066.Travel-Guide-VacationRentals)[Flights to Fairfield](https://expedia.ca/Cheap-Flights-To-Fairfield.d8066.Travel-Guide-Flights)[Fairfield Car Rentals](https://expedia.ca/Car-Rentals-In-Fairfield.d8066.Car-Rental-Guide)[Fairfield Vacation Packages](https://expedia.ca/Fairfield.d8066.Destination-Travel-Guides) ![Sunset at Ash Creek marina, Fairfield, Connecticut.](https://images.trvl-media.com/place/8066/539b61d4-b6c3-42c3-ab50-495da559bb28.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/8066/539b61d4-b6c3-42c3-ab50-495da559bb28.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 Fairfield Hotels with a Pool Tonight [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=8066&startDate=2026-01-13&endDate=2026-01-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=8066&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8066&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=8066&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Fairfield hotels with a pool ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/1e666ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/b1e811bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Kitchenette](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/d7a51c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/58982240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Circle Hotel Fairfield [](https://www.expedia.ca/New-Haven-Hotels-The-Circle-Hotel-Fairfield.h9816438.Hotel-Information) Grasmere 9.0/10 Wonderful (1,432 reviews) "Great room, clean, spacious. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George [](https://www.expedia.ca/New-Haven-Hotels-The-Circle-Hotel-Fairfield.h9816438.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/86f9c0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/0e6e3fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/ec029251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114300000/114291600/114291600/9f9cf405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna [](https://www.expedia.ca/Fairfield-Hotels-Luxury-Estate-W-Heated-Pool.h114291600.Hotel-Information) Tunxis Hill 10/10 Exceptional (1 review) "The Host was welcoming and responsive to our inquiries!Our stay was wonderful! The property was spectacular and offered all the amenities we needed for a comfortable and enjoyable visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia B. CA $1,079 CA $2,766 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Fairfield-Hotels-Luxury-Estate-W-Heated-Pool.h114291600.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/104000000/103680000/103678300/103678239/8da8a027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Westport)](https://images.trvl-media.com/lodging/104000000/103680000/103678300/103678239/cdf5c76b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103680000/103678300/103678239/1e3a1b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103680000/103678300/103678239/69e1e488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delamar Westport [](https://www.expedia.ca/Westport-Hotels-Delamar-Westport.h103678239.Hotel-Information) Westport 10/10 Exceptional (2 reviews) "Very clean, friendly staff, helpful, and wonderful breakfast buffet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jack CA $219 CA $252 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Westport-Hotels-Delamar-Westport.h103678239.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/593124d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/49253eeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/0a1f1c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf, Spa & Conference Center [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) Southbury 8.4/10 Very good (1,003 reviews) "Very nice, staff were excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $152 CA $199 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/eba50eaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/a12e56fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/68510516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/ff093bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Shelton [](https://www.expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) Shelton 8.4/10 Very good (1,005 reviews) "cleanliness and the people were pleasant at the desk as well as in the café area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) hartley CA $161 CA $185 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/ba785aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/84719ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/5af2dc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/268b5ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Milford [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.Hotel-Information) Milford 8.4/10 Very good (1,005 reviews) "Very nice hotel clean friendly convenient location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $136 CA $156 total includes taxes & fees Jan 24 - Jan 25 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.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) ![Lobby](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/95bf4352.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) ### Homewood Suites by Hilton Orange New Haven [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) Orange 9.2/10 Wonderful (1,006 reviews) "Nice roomy room, clean, comfortable bed, plenty of hot water " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $145 CA $166 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/ad77ef5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/4328324a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/7721b0e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Shelton [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) Shelton 8.8/10 Excellent (1,006 reviews) "Beautiful hotel in great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tara CA $147 CA $169 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/5000000/4790000/4780400/4780357/ab1927b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite | Living area](https://images.trvl-media.com/lodging/5000000/4790000/4780400/4780357/fd1f9a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite | In-room dining](https://images.trvl-media.com/lodging/5000000/4790000/4780400/4780357/d9b8b932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Suite | Living area](https://images.trvl-media.com/lodging/5000000/4790000/4780400/4780357/a1cac1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet Inn & Suites Centerport [](https://www.expedia.ca/Centerport-Hotels-Chalet-Inn-Suites-Centerport.h4780357.Hotel-Information) Centerport 7.8/10 Good (766 reviews) "Great location Rooms are " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $167 CA $190 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Centerport-Hotels-Chalet-Inn-Suites-Centerport.h4780357.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/fd93f670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/c4603508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/7d962b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/6855e0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 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) West Haven 8.0/10 Very good (1,529 reviews) "Decent hotel for the price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexa CA $133 CA $153 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.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=2026-01-27&endDate=2026-01-28®ionId=8066&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Fairfield Hotel Reviews ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Clean room, nice view, courteous staff and smooth check-in/check-out experience. Breakfast was a nice compliment." [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "The room was very nice, the hotel is beautiful and very inviting. Special shout out to Mohammed and Ruben in the dining area" [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ![Hampton Inn by Hilton Shelton](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Yes " [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![The Circle Hotel Fairfield](https://images.trvl-media.com/lodging/10000000/9820000/9816500/9816438/b1e811bb_y.jpg) ### The Circle Hotel Fairfield 10/10 Excellent "Great room, clean, spacious. Would definitely stay here again. " [](https://expedia.ca/New-Haven-Hotels-The-Circle-Hotel-Fairfield.h9816438.Hotel-Information) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Yes" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Norwalk Inn & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15200/15114/13ab5174_y.jpg) ### Norwalk Inn & Conference Center 10/10 Excellent "The room was clean and spotless. The staff was very friendly at check-in. Overall, I would definitely choose the Norwalk Inn on my next visit to Norwalk, CT." [](https://expedia.ca/Stamford-Hotels-Norwalk-Inn.h15114.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Stamford / New York City](https://images.trvl-media.com/lodging/1000000/30000/25000/24963/af81668d_y.jpg) ### La Quinta Inn & Suites by Wyndham Stamford / New York City 10/10 Excellent "Thx" [](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg) ### DoubleTree by Hilton Stamford 10/10 Excellent "The customer service was absolutely amazing" [](https://expedia.ca/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.Hotel-Information) ![Motel 6 Milford, CT](https://images.trvl-media.com/lodging/1000000/10000/300/291/4c692d71_y.jpg) ### Motel 6 Milford, CT 10/10 Excellent "Elevador no sirve" [](https://expedia.ca/New-Haven-Hotels-Motel-6-Milford.h291.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Fairfield with outdoor pools? > Guests rave about the friendly and wonderful staff, who go above and beyond to ensure a pleasant stay. The hotel also offers a complimentary breakfast, featuring delicious options that guests appreciate, especially on weekends. With a traveller review score of 9.0, it's clear that families value the clean and comfortable rooms, making it an ideal spot for those looking for convenience and quality. ### How much does a hotel with outdoor pool in Fairfield cost? ### Are there hotels with outdoor pools that are close to Penfield Beach? > This hotel also stands out for its complimentary breakfast, which is a fantastic perk, especially for families eager to start their day off right. Reviewers praise the variety of options available, noting that the breakfast is both free and delicious. The Circle Hotel Fairfield has earned an excellent traveller rating of 9.0, reflecting its reputation for clean and comfortable rooms, friendly staff, and a convenient location. ### Is it cheaper to book flights and a hotel in Fairfield as a package? ### How can I save on a hotel in Fairfield with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Bridgeport ](https://www.expedia.ca/4Star-Bridgeport-Hotels.s40-0-d525.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Bridgeport ](https://www.expedia.ca/5Star-Bridgeport-Hotels.s50-0-d525.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Westport ](https://www.expedia.ca/5Star-Westport-Hotels.s50-0-d56054.Travel-Guide-Filter-Hotels) - [B&B in Bridgeport ](https://www.expedia.ca/Bridgeport-Bed-And-Breakfast.d525-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Capsule Hotels in Bridgeport ](https://www.expedia.ca/Bridgeport-Capsule-Hotels.d525-aaCapsuleHotels.Travel-Guide-Accommodation) - 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