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 $145 ![](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 [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-10-15&endDate=2025-10-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-10-16&endDate=2025-10-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183065&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Middlebury Hotels with a Pool ![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/a3c0d287.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 (1009) "The rooms were clean and staff were very attentive." CA $126 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2.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) ### Holiday Inn Express Southington by IHG Southington 8.8/10 Excellent (1127) "excellent hotel,room clean and excellent service." CA $132 CA $152 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155.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) ### Wyndham Southbury Southbury 8.2/10 Very good (1023) "The hotel was easily accessible from the main highways. Nice location. " CA $130 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/f44c391a.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) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection Southbury 8.4/10 Very good (1004) "Great stay!!" CA $160 CA $203 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Danbury-Hotels-Heritage-Hotel.h35389.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) ![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 (899) "Great place stayed several times." CA $147 CA $170 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.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 (1003) "This property is very relaxing " CA $135 CA $155 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/268b5ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 18.00 per person)](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/c174ee1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2473700/2473639/b8a2e8a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Milford Milford 8.4/10 Very good (1012) "This hotel is wonderful." CA $149 CA $171 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Milford.h2473639.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) ![Down comforters, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/cd756b94.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Shelton Shelton 8.6/10 Excellent (1006) "Perfect location, convenient to everything Friendly staff, clean room " CA $160 CA $184 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31f305c2.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) ![Room](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/31e09d21.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) ### Home2 Suites by Hilton Bristol Bristol 9.4/10 Exceptional (143) "I would stay here again! " CA $183 CA $210 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/1f053b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/f4d4e3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/0fc1d688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445733/28b95632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Danbury Danbury 9.0/10 Wonderful (1008) "Amazing place" CA $172 CA $197 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Danbury-Hotels-Hampton-Inn-Danbury.h1445733.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=2025-10-29&endDate=2025-10-30®ionId=183065&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Middlebury Hotel Reviews ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Simple, elegant decir and comfortable room. Good access to charging stations, hvac operated as it should, excellent breakfast options—more than continental. Friendly check-in manager. Needs a bit of paint on doors and door woodwork but our 2nd time here and would recommend. " [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Clarion Inn](//images.trvl-media.com/lodging/1000000/10000/7600/7519/36377da0_y.jpg) ### Clarion Inn 10/10 Excellent "Great." [](https://expedia.ca/North-Haven-Hotels-Clarion-Inn.h7519.Hotel-Information) ![Hilton Garden Inn Shelton](//images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "Clean room quiet " [](https://expedia.ca/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.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 "The front and interior of the building is beautiful. The back parking lot was a bit overgrown and the rear entry didnt close automatically. Otherwise, a clean, comfortable place to sleep after a long day. " [](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 "Very nice staff" [](https://expedia.ca/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.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 "Check in was easy. Everything work. So fart it s a good place" [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Hyatt Place Milford / New Haven](//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) ![Wyndham Southbury](//images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "This was a convenient stay for us while visiting family in the area, and a good value compared to others in the area. Happy that they had laundry facilities. Complimentary coffee was not half bad! Bathroom is small. Fitness room has no WiFi or cell signal. Both of those are minor things though. Staff was super friendly and helpful." [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![Trumbull Marriott Shelton](//images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 10/10 Excellent "Clean room, Staff was great - parking was simple" [](https://expedia.ca/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middlebury? > [Trumbull Marriott Shelton](https://www.expedia.ca/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information): Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. [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): Features full, a pool, and free self parking. [Holiday Inn Express Southington by IHG](https://www.expedia.ca/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information): Provides a snack bar/deli, 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): Hotel located near Quinnipiac University. Offers buffet, an indoor pool, and complimentary wired internet access. ### 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, Brass Mill Center, and Beacon Falls Town Recreation Field 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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