Title: Book the Best Hotels with POOL in Middlebury in 2025 | Expedia.ca [Hotels in Middlebury](https://expedia.ca/Middlebury-Hotels.d183065.Travel-Guide-Hotels)[Vacation Rentals in Middlebury](https://expedia.ca/Middlebury-Vacation-Rentals.d183065.Travel-Guide-VacationRentals)[Middlebury Car Rentals](https://expedia.ca/Car-Rentals-In-Middlebury.d183065.Car-Rental-Guide)[Middlebury Vacation Packages](https://expedia.ca/Middlebury.d183065.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/cda26adfd6cf208eeb474889dc27ce3a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brandon Miller # Find Hotels with a Pool in Middlebury, CT from CA $141 - ![](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 Middlebury Hotels with a Pool Tonight [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-11-03&endDate=2025-11-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 4 - Nov 5](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-11-04&endDate=2025-11-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlebury Hotels with a Pool ![Pool](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31f305c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/d26781d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/ebe022ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Bristol Bristol 9.6/10 Exceptional (152) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LARRY CA $182 CA $209 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f224bafd.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) ![Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/3fa625b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection Southbury 8.4/10 Very good (1007) "Very lovely hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy M CA $160 CA $203 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.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) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/f60a5e9b.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) ### Holiday Inn Express Southington by IHG Southington 8.6/10 Excellent (1148) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $132 CA $152 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/95bfeb2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 16.95 per person)](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/e45c4a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/0b53186c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/d56a5b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Southbury Southbury 8.2/10 Very good (1014) "Clean, nice, super convenient. Great restaurants in the area. Beautiful setting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courtney CA $130 CA $149 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/0494208e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/b6f421aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/252d4dc3.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/3000000/2080000/2078500/2078403/e4131984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites New Haven - South - West Haven West Haven 8.4/10 Very good (1001) "Great breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elyse CA $123 CA $141 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-Suites-New-Haven-South-West-Haven.h2078403.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) ![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) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/10000/9965/9c0a3e55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Plainville Plainville 8.6/10 Excellent (903) "Great stay would and will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $122 CA $141 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.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) ![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/2000000/1810000/1802800/1802750/44e097e7.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) ### Holiday Inn Cheshire - Southington by IHG Southington 8.2/10 Very good (1008) "The rooms were clean and staff were very attentive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodger CA $140 CA $161 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/ff6d89d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New England Inn & Suites Berlin 8.6/10 Excellent (1014) "arrived at 9:30 pm as a single woman and felt very safe " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie CA $134 CA $155 total includes taxes & fees Nov 10 - Nov 11 [](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/1000000/20000/16500/16474/9bab7633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/42dbd033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/382d4dcb.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/1000000/20000/16500/16474/a76a124a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Danbury-Bethel Danbury 8.6/10 Excellent (524) "Hotel was very clean, front desk ladies were nice and polite, breakfast was great. Love the dove soap, shampoo and conditioner. Hotel was in a great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DeAsia CA $136 CA $156 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Danbury-Hotels-Comfort-Inn-Suites-Danbury-Bethel.h16474.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/a5488d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Arcade](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/cb5c00ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/d2bf1069.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15100/15069/b3e4a390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Danbury Danbury 8.4/10 Very good (1005) "Generally an ok stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $127 CA $146 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Danbury-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Danbury.h15069.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=2025-11-18&endDate=2025-11-19®ionId=183065&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Middlebury Hotel Reviews ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "The room was very clean. It was a great stay." [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](//images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "Brian, front of house, kind and excellent communicator!" [](https://expedia.ca/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ![Wyndham Southbury](//images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "Yes" [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![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 "My 3, well (2½) day stay was overall not bad untill........ On My 2 day of booking the room i was asked by the the woman with a clip board who im assuming was the head of in house keeping if i was staying for another day which i had told her yes and she asked would i be needing house keeping to go in my room which i replied no alls i need is fresh towels......" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](//images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "JUST GOING TO VISIT GRANDCHILDREN IN CT...USED HOTELS .COM FOR RESERVATION THE HOTEL WAS NICER AND CLEANER THEN EXPECRED...PERFECT NIGHT'S SLEEP...I WOULD RECOMMEND THIS TRAVELING IN THE HARRISBURG VA AREA¡!" [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Clarion Inn](//images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "Very clean " [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.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 "Room was immaculate; the staff was friendly and prompt Breakfast area neatly arranged. Will go back for sure" [](https://expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](//images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "Ms Washington was wonderful and handled a very stressful check in line well." [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Hampton Inn by Hilton Shelton](//images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Clean room efficient checkout " [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middlebury? > [Holiday Inn Express Southington by IHG](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.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): Provides a snack bar/deli, an indoor pool, and complimentary wired internet access. [Wyndham Southbury](https://www.expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information): Features 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): Provides a seasonal outdoor pool, an indoor pool, and 2 restaurants. [Hyatt Place Milford / New Haven](https://www.expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information): Offers complimentary wired internet access, an indoor pool, and free self parking. ### What is there to see and do in Middlebury? > Make a point to visit attractions like Lake Quassapaug and Quassy Amusement Park. Discover sights such as Palace Theatre, Holy Land USA, and Brass Mill Center during your stay. ### When is the best time to book a hotel with a pool in Middlebury? > You may want to consider a place to stay that has an outdoor pool if you plan to visit Middlebury in the hottest months of July, August, or June when the average temperature is 69°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 32°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in Oakville](https://www.expedia.ca/5Star-Oakville-Hotels.s50-0-d3000430361.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Connecticut](https://www.expedia.ca/Destinations-In-Connecticut-Hotel-With-Early-Check-In.0-0-d208-thotelwithearlycheckin.Hotel-Filter-Destinations) - [Hotels with a Pool in Connecticut](https://www.expedia.ca/Destinations-In-Connecticut-Hotel-With-Pool.0-0-d208-tHotelwithPool.Hotel-Filter-Destinations) - [Hotels with Balconies in Connecticut](https://www.expedia.ca/Destinations-In-Connecticut-Hotels-With-Balconies.0-0-d208-tHotelswithBalconies.Hotel-Filter-Destinations) - [Hotels with Childcare in Connecticut](https://www.expedia.ca/Destinations-In-Connecticut-Hotels-With-Childcare.0-0-d208-tHotelswithChildcare.Hotel-Filter-Destinations) - 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