Title: The Best Middlebury Hotels with Pools from $100 - Hotels with indoor pools in Middlebury, CT | Expedia.com [Middlebury Travel Guide](https://expedia.com/Middlebury.dx183065)[Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d183065.Travel-Guide-Hotels)[Vacation Rentals in Middlebury](https://expedia.com/Middlebury-Vacation-Rentals.d183065.Travel-Guide-VacationRentals)[Flights to Middlebury](https://expedia.com/Cheap-Flights-To-Middlebury.d183065.Travel-Guide-Flights)[Car Rentals in Middlebury](https://expedia.com/Car-Rentals-In-Middlebury.d183065.Car-Rental-Guide)[Middlebury Vacation Packages](https://expedia.com/Middlebury.d183065.Destination-Travel-Guides) ![Either off access road at the end of Old Waterbury Rd, or Umberfield Rd. Abandoned in the woods near I 84 and power lines overhead.](https://images.trvl-media.com/place/10425/0361f1ad-051a-4c95-a6dc-c4b5531475e6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brandon Miller ![](https://images.trvl-media.com/place/10425/0361f1ad-051a-4c95-a6dc-c4b5531475e6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 [Mar 14 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-03-14&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 15 - Mar 16](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-03-15&endDate=2026-03-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middlebury hotels with a pool ![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 | Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/d9e2e7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/922200/922173/e3c0e906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New England Inn & Suites [](https://www.expedia.com/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) Berlin 8.6/10 Excellent (1,000 reviews) - Dive into refreshing luxury at an indoor pool retreat where wellness meets comfort and convenience. $87 nightly $100 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Hartford-Hotels-Best-Western-Plus-New-England-Inn-Suites.h922173.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/a84dbb59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/2a17dd67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/837ff7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/beb7cb97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heritage Hotel, Golf & Conference Center [](https://www.expedia.com/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) Southbury 8.4/10 Very Good (1,001 reviews) - Dive into saltwater serenity at this mountain spa retreat with indoor and seasonal outdoor pools. $127 nightly $146 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Southbury-Hotels-Heritage-Hotel.h35389.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) ![Exterior](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/7588ab8c.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) ![Sports facility](https://images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/d26781d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Bristol [](https://www.expedia.com/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) Bristol 9.6/10 Exceptional (198 reviews) - Serene hotel with an indoor pool escape just steps away from relaxing in a soothing hot tub. $130 nightly $150 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/d045ec83.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) ![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) ### Holiday Inn Express Southington by IHG [](https://www.expedia.com/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) Southington 8.6/10 Excellent (1,233 reviews) - Immerse in the refreshing seasonal outdoor pool, a perfect summertime retreat with convenient morning to evening hours. $88 nightly $101 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/cd90eec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/b49eb2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/3b2d1292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16500/16474/a68d49ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Danbury-Bethel [](https://www.expedia.com/Danbury-Hotels-Comfort-Inn-Suites-Danbury-Bethel.h16474.Hotel-Information) Danbury 8.6/10 Excellent (604 reviews) - Splash into sunny leisure at this hotel's seasonal outdoor pool, perfect for summer refreshment in Danbury. $109 nightly $125 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Comfort-Inn-Suites-Danbury-Bethel.h16474.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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/3d5d12d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/d56a5b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Southbury [](https://www.expedia.com/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) Southbury 8.2/10 Very Good (1,140 reviews) - Dive into refreshing year-round aquatics at this Southbury hotel, where the indoor pool beckons after a day of exploration. $93 nightly $107 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/42d801c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/c70440c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/3879ce24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/891500/891471/436ff60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard By Marriott Danbury [](https://www.expedia.com/Danbury-Hotels-Courtyard-By-Marriott-Danbury.h891471.Hotel-Information) Danbury 9.0/10 Wonderful (495 reviews) - Splash into relaxation at this pristine indoor pool oasis just steps from hiking trails. $111 nightly $128 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Courtyard-By-Marriott-Danbury.h891471.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/1000000/30000/23300/23217/7d962b8e.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) ![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.com/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) West Haven 8.0/10 Very Good (1,566 reviews) - Dive into this indoor pool paradise, just steps from New Haven's top attractions. $95 nightly $109 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/0e1f3025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/ee4e9e41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/2f812c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/21d5040e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Hartford/Farmington [](https://www.expedia.com/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) Farmington 8.8/10 Excellent (1,001 reviews) - Swim and unwind at this stylish retreat where guests adore the indoor pool and hot tub for year-round aquatic relaxation. $122 nightly $141 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Free WiFi](https://images.trvl-media.com/lodging/119000000/118250000/118243000/118242924/672e514a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/119000000/118250000/118243000/118242924/w3836h2556x4y4-79ec55d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites By Hilton North Haven [](https://www.expedia.com/North-Haven-Hotels-Hampton-Inn-Suites-By-Hilton-North-Haven.h118242924.Hotel-Information) North Haven $128 nightly $147 total Apr 14 - Apr 15 Total with taxes and fees [](https://www.expedia.com/North-Haven-Hotels-Hampton-Inn-Suites-By-Hilton-North-Haven.h118242924.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.com/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30®ionId=183065&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Middlebury Breakfast included Hot tub 4 stars 5 stars Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_183065) ## Top Middlebury Hotel Reviews ![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/7d962b8e_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 8/10 Good "Breakfast is ok. Staff is very nice and friendly. " [](https://expedia.com/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/9672e16a_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "Fitness center is limited to a few dumbbells and treadmills. The made to order breakfast is limited in selection, but very good. Everything else was standard holiday inn. Good place to stay." [](https://expedia.com/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Clean room, friendly staff. Great stay for business trip" [](https://expedia.com/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/f9413aba_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 6/10 Okay "The hot tub was cold during our entire stay" [](https://expedia.com/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/a12e56fc_y.jpg) ### Hyatt House Shelton 10/10 Excellent "Clean room, plenty of amenities " [](https://expedia.com/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) ![Trumbull Marriott Shelton](https://images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 10/10 Excellent "Great customer service " [](https://expedia.com/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ![Courtyard by Marriott New Haven Orange-Milford](https://images.trvl-media.com/lodging/1000000/80000/79500/79426/d5c6959e_y.jpg) ### Courtyard by Marriott New Haven Orange-Milford 10/10 Excellent "Nice place to stay. Accessible and comfortable." [](https://expedia.com/New-Haven-Hotels-Courtyard-By-Marriott-New-Haven-Orange-Milford.h79426.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/5fee96a0_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "Staff was great and very friendly " [](https://expedia.com/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/06fc08bd_y.jpg) ### Holiday Inn Express Southington by IHG 8/10 Good "Breakfast was not the best but good." [](https://expedia.com/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Middlebury? ### What is there to see and do in Middlebury? ### When is the best time to book a hotel with a pool in Middlebury? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Quassy Amusement Park ](https://www.expedia.com/Quassy-Amusement-Park-Hotels.0-l6089847-0.Travel-Guide-Filter-Hotels) - [Hotels near Hop Brook Lake ](https://www.expedia.com/Hop-Brook-Lake-Hotels.0-l553248621561886346-0.Travel-Guide-Filter-Hotels) - [Hotels near Waterbury - Oxford ](https://www.expedia.com/Waterbury-Oxford-Airport-Hotels.0-aOXC-0.Travel-Guide-Filter-Hotels) - [Flights to Connecticut ](https://www.expedia.com/Destinations-In-Connecticut.d208.Flight-Destinations) - [Flights from Waterbury - Oxford ](https://www.expedia.com/lp/airports/oxc/flights-from-waterbury-oxford-airport) - [Flights from Raleigh (RDU) to Oxford (OXC) ](https://www.expedia.com/lp/flights/rdu/oxc/raleigh-to-oxford) - 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