Title: Book the Best Hotels with POOL in Winchester in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6046207.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d6046207.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Winchester, IN from CA $66 - ![](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 Winchester Hotels with a Pool Tonight [Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-04&endDate=2025-12-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-05&endDate=2025-12-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6046207&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/77a3466c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/7c7790c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/w992h749x8y1-a775c4b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/fee1facc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Randolph Inn and Suites Winchester 9.0/10 Wonderful (243) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William [](https://www.expedia.ca/Muncie-Hotels-Randolph-Inn-And-Suites.h1778532.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/317bd989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/8c4791db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/d689bf19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/93000000/92420000/92418500/92418479/6e3a4720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Richmond 9.4/10 Exceptional (647) "Room was clean, front desk was friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $130 CA $149 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Richmond-Hotels-Comfort-Suites.h92418479.Hotel-Information) ![Indoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/9a7ba01e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/69321973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/bca78e68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard King Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/25900/25869/ebc0f494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn and Conference Center Richmond 6.8/10 (1002) "nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Onda CA $59 CA $66 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Richmond-Hotels-Quality-Inn-And-Conference-Center.h25869.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/4f171030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/449ea658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking (Mobility, Bathtub w/Grab Bars)](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/8273535b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Richmond I-70 Richmond 8.4/10 Very good (1000) "Good motel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Parth CA $94 CA $105 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/ff6e0c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/b66d8027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible (Comm, Mobil, Roll-In Shower)](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/267bdaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1880900/1880898/02bf683d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Portland by IHG Portland 9.2/10 Wonderful (354) "Excellent stay every time we are there friendly staff all around awesome stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $140 CA $156 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Muncie-Hotels-Holiday-Inn-Express-Suites-Portland.h1880898.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/451c7d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food court](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/0c112d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d0795775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Richmond Indiana I-70 Richmond 8.4/10 Very good (1000) "New facility, best hotel I’ve stayed in recently!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antonia CA $130 CA $146 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/56a546ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/f7718af5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/57d10bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/60000/52900/52875/b8fcba4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn by Marriott Richmond New Paris 9.0/10 Wonderful (517) "The room was clean, the staff was polite and friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $141 CA $160 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Dayton-Hotels-Fairfield-Inn-By-Marriott-Richmond.h52875.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/d624271a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/7c887688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/a50de8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/d185387c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Richmond, IN Richmond 9.2/10 Wonderful (938) "The breakfast service was excellent tasty and well presented " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terence CA $140 CA $156 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Richmond-Hotels-Hampton-Inn-Suites-Richmond.h1590037.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/870000/861300/861235/0d98eade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/870000/861300/861235/a0d3d74c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/870000/861300/861235/99f5a524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/870000/861300/861235/3fba3107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Greenville by IHG Greenville 8.6/10 Excellent (300) "Everything was very nice at this location. Before I found this location I was staying in Richmond to be at a Hilton property. Now that there is something clean and kept I will continue to stay here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice CA $167 CA $190 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Sidney-Hotels-Holiday-Inn-Express-Hotel-Suites-Greenville.h861235.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/67500/67438/29e2cdda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/70000/67500/67438/e0a75b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/67500/67438/170ead88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/70000/67500/67438/7aec57df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Muncie Place Hotel & Suites Muncie 8.0/10 Very good (598) "Staff was very friendly and property was great for our two (2) fur babies. Will stay here again if in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $122 CA $136 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Muncie-Hotels-Holiday-Inn-Express-Hotel-Suites-Muncie.h67438.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=2025-12-18&endDate=2025-12-19®ionId=6046207&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Motel 6 Richmond, IN](https://images.trvl-media.com/lodging/1000000/60000/50200/50102/3e0f69fd_y.jpg) ### Motel 6 Richmond, IN 10/10 Excellent "The checkin was quick and easy. " [](https://expedia.ca/Richmond-Hotels-Motel-6-Richmond.h50102.Hotel-Information) ![Hampton Inn & Suites Richmond, IN](https://images.trvl-media.com/lodging/2000000/1600000/1590100/1590037/1e53a5db_y.jpg) ### Hampton Inn & Suites Richmond, IN 10/10 Excellent "Excellent service at check in!" [](https://expedia.ca/Richmond-Hotels-Hampton-Inn-Suites-Richmond.h1590037.Hotel-Information) ![Comfort Inn & Suites Muncie Near University](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141769/6054e777_y.jpg) ### Comfort Inn & Suites Muncie Near University 10/10 Excellent "The room was clean and the staff very courteous. " [](https://expedia.ca/Muncie-Hotels-Comfort-Inn-Suites-Muncie.h2141769.Hotel-Information) ![Muncie Place Hotel & Suites](https://images.trvl-media.com/lodging/1000000/70000/67500/67438/29e2cdda_y.jpg) ### Muncie Place Hotel & Suites 10/10 Excellent "This hotel is nice. Location is close to university, shopping, restaurants. Has an outdoor patio area to sit at. Pool area and fitness room was nice. Hotel and parking lot was very clean. Staff was wonderful especially Ms Sonda and Ms Jama on the breakfast area. Not only were they both friendly, but both of these ladies kept the food stocked, and the eating area clean. " [](https://expedia.ca/Muncie-Hotels-Holiday-Inn-Express-Hotel-Suites-Muncie.h67438.Hotel-Information) ![Best Western Plus Richmond Indiana I-70](https://images.trvl-media.com/lodging/1000000/260000/251600/251530/d93a0730_y.jpg) ### Best Western Plus Richmond Indiana I-70 10/10 Excellent "We were very pleased with our stay. The place felt new and was so nicely decorated for the holiday! It felt cozy and comfortable. Breakfast was hot and tasty, my girls loved making their own waffles (bonus seasonal flavor!). I enjoyed the biscuits and gravy and fluffy scrambled eggs. We had a peaceful rest in comfortable beds and weren't disturbed by the highway. There are lots of convenient places to eat and shop at. I chose this location because of close proximity to a mall and a roller skate rink! " [](https://expedia.ca/Richmond-Hotels-Best-Western-Classic-Inn.h251530.Hotel-Information) ![Baymont by Wyndham Richmond I-70](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944_y.jpg) ### Baymont by Wyndham Richmond I-70 10/10 Excellent "Everyone was friendly, the rooms were clean. I will say the pictures make it look nicer than it is but still a great stay!" [](https://expedia.ca/Richmond-Hotels-Comfort-Inn-Richmond-I-70.h4345.Hotel-Information) ![Courtyard Muncie at Horizon Convention Center](https://images.trvl-media.com/lodging/13000000/12760000/12755900/12755848/6aef882b_y.jpg) ### Courtyard Muncie at Horizon Convention Center 10/10 Excellent "Excellent!" [](https://expedia.ca/Muncie-Hotels-Courtyard-Muncie-At-Horizon-Convention-Center.h12755848.Hotel-Information) ![Baymont by Wyndham Muncie Near Ball State University](https://images.trvl-media.com/lodging/1000000/10000/3300/3204/39faaa1f_y.jpg) ### Baymont by Wyndham Muncie Near Ball State University 10/10 Excellent "Very nice " [](https://expedia.ca/Muncie-Hotels-Baymont-By-Wyndham-Muncie-Near-Ball-State-University.h3204.Hotel-Information) ![Fairfield Inn by Marriott Muncie](https://images.trvl-media.com/lodging/1000000/20000/14300/14243/9762721b_y.jpg) ### Fairfield Inn by Marriott Muncie 8/10 Good "Breakfast was very good and fresh each morning. The staff was extremely nice, friendly and helpful. My only complaint was my trash was not emptied 2 of the days, but i told the front desk and they sent someone right away to do it. " [](https://expedia.ca/Muncie-Hotels-Fairfield-Inn-By-Marriott-Muncie.h14243.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winchester? ### What is there to see and do in Winchester? ### When is the best time to book a hotel with a pool in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [5 Star Hotels in East Central Indiana ](https://www.expedia.ca/5Star-East-Central-Indiana-Hotels.s50-0-d6233870.Travel-Guide-Filter-Hotels) - [Apartments in Albany ](https://www.expedia.ca/Albany-Apartments.d553248634983410143-aaApartments.Travel-Guide-Accommodation) - [Cheap Hotels in Albany ](https://www.expedia.ca/Albany-Hotels-Cheap-Hotels.0-0-d553248634983410143-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Albany ](https://www.expedia.ca/Albany-Hotels-Hotel-With-Pool.0-0-d553248634983410143-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Albany Hotels ](https://www.expedia.ca/Albany-Hotels.d553248634983410143.Travel-Guide-Hotels) - 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