Title: Book the Best Hotels with POOL in Cleveland in 2025 | Expedia.ca [Hotels in Cleveland](https://expedia.ca/Cleveland-Hotels.d3000461538.Travel-Guide-Hotels)[Vacation Rentals in Cleveland](https://expedia.ca/Cleveland-Vacation-Rentals.d3000461538.Travel-Guide-VacationRentals)[Cleveland Car Rentals](https://expedia.ca/Car-Rentals-In-Cleveland.d3000461538.Car-Rental-Guide)[Cleveland Vacation Packages](https://expedia.ca/Cleveland.d3000461538.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 Cleveland, WI from CA $110 - ![](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 Cleveland Hotels with a Pool Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=3000461538&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=3000461538&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000461538&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000461538&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cleveland Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/18000/17917/daa7c361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/18000/17917/cb697ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Accessible, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/18000/17917/d6bb0d42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18000/17917/360e4c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Sheboygan North I-43 Sheboygan 8.2/10 Very good (732) "Thank you for the stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd CA $99 CA $113 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Sheboygan-Hotels-Quality-Inn.h17917.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1750000/1740500/1740463/140b115c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1750000/1740500/1740463/8c136dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lakeside Two Queen Beds | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1750000/1740500/1740463/1671d084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, beach views ](https://images.trvl-media.com/lodging/2000000/1750000/1740500/1740463/b6f6a12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lighthouse Inn Two Rivers 8.8/10 Excellent (1000) "Friendly staff, clean room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $147 CA $167 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Sheboygan-Hotels-Lighthouse-Inn.h1740463.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/670000/663100/663055/73bd7f15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/670000/663100/663055/6a44c8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/663100/663055/ea3b9a85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/670000/663100/663055/9841254f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Sheboygan Sheboygan 8.6/10 Excellent (1002) "Nice room and friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $112 CA $127 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Sheboygan-Hotels-AmericInn-By-Wyndham-Sheboygan.h663055.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/91000000/90180000/90172600/90172531/1f357835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-golf](https://images.trvl-media.com/lodging/91000000/90180000/90172600/90172531/90244372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/91000000/90180000/90172600/90172531/0c64b383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/91000000/90180000/90172600/90172531/8011a80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Village Inn on the Lake Two Rivers 8.8/10 Excellent (152) "Friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ane CA $138 CA $157 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Two-Rivers-Hotels-Village-Inn-On-The-Lake.h90172531.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/930000/921400/921389/df0956b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/930000/921400/921389/2dd9d6b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/930000/921400/921389/757ddf30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/930000/921400/921389/905df2d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Sheboygan I-43 Sheboygan 8.6/10 Excellent (130) "nice and clean hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $106 CA $120 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Sheboygan-Hotels-Sleep-Inn-Suites-Sheboygan-I-43.h921389.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/8100/8038/35a9e66c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8100/8038/be8c422d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/8100/8038/f21a516b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8100/8038/bd886547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Manitowoc by IHG Manitowoc 8.2/10 Very good (534) "Modern! A lot of food options!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roman CA $127 CA $144 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Sheboygan-Hotels-Holiday-Inn-Manitowoc.h8038.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/22000000/21350000/21346300/21346254/170ee4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/22000000/21350000/21346300/21346254/3293ebc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Historic Hotel (Accessible by Stairs) - One Queen - Shared Bath](https://images.trvl-media.com/lodging/22000000/21350000/21346300/21346254/0b28f1bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/22000000/21350000/21346300/21346254/6923e756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siebkens Resort Elkhart Lake 9.2/10 Wonderful (234) "I loved the historic atmosphere… short walk to the lake and a quaint on site bar and restaurant. I really enjoyed their house made granola for breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $162 CA $182 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Sheboygan-Hotels-Siebkens-Resort.h21346254.Hotel-Information) ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/71000000/70550000/70542900/70542875/be2dadad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Queen Beds](https://images.trvl-media.com/lodging/71000000/70550000/70542900/70542875/67e05dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/71000000/70550000/70542900/70542875/d914aa7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/71000000/70550000/70542900/70542875/1b627dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oasis Hotel & Bar Sheboygan Falls 8.2/10 Very good (332) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherry CA $99 CA $110 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Sheboygan-Falls-Hotels-AmeriVu-Inn-Suites.h70542875.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/46000000/45950000/45946900/45946864/a8b439ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/46000000/45950000/45946900/45946864/b2988a25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/46000000/45950000/45946900/45946864/9a044811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/46000000/45950000/45946900/45946864/00a83619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cobblestone Hotel & Suites - Two Rivers Two Rivers 8.8/10 Excellent (802) "The room was immaculate! Beds were super comfortable! The breakfast had many choices and the dining area overlooks the lake and rivers! Staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci [](https://www.expedia.ca/Sheboygan-Hotels-Cobblestone-Hotel-Suites-Two-Rivers.h45946864.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1062800/1062718/f9a24178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1070000/1062800/1062718/65535b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1062800/1062718/4453439b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking (One-Bedroom)](https://images.trvl-media.com/lodging/2000000/1070000/1062800/1062718/1bd30c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Plymouth Plymouth 9.0/10 Wonderful (554) "Nice, quiet room and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darrel CA $153 CA $174 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Sheboygan-Hotels-Baymont-By-Wyndham-Plymouth.h1062718.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=2025-12-04&endDate=2025-12-05®ionId=3000461538&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Cleveland Hotel Reviews ![Lighthouse Inn](https://images.trvl-media.com/lodging/2000000/1750000/1740500/1740463/1671d084_y.jpg) ### Lighthouse Inn 10/10 Excellent "Friendly staff, clean room." [](https://expedia.ca/Sheboygan-Hotels-Lighthouse-Inn.h1740463.Hotel-Information) ![Best Western Stanton Inn](https://images.trvl-media.com/lodging/1000000/920000/911900/911819/3d361bf0_y.jpg) ### Best Western Stanton Inn 10/10 Excellent " Very nice hotel, quiet area, pleasant staff. Room was spotless. Only complaint was the shower, the door doesn't close, so the floor gets soaked from splashing water. Kind of weird, but the bathroom was nice." [](https://expedia.ca/Sheboygan-Hotels-Best-Western-Stanton-Inn.h911819.Hotel-Information) ![Harbor Town Inn, BW Signature Collection](https://images.trvl-media.com/lodging/1000000/870000/861600/861528/7380bf3c_y.jpg) ### Harbor Town Inn, BW Signature Collection 10/10 Excellent "Nice staff clean" [](https://expedia.ca/Sheboygan-Hotels-Harbor-Town-Inn.h861528.Hotel-Information) ![Holiday Inn Manitowoc by IHG](https://images.trvl-media.com/lodging/1000000/10000/8100/8038/35a9e66c_y.jpg) ### Holiday Inn Manitowoc by IHG 10/10 Excellent "Modern! A lot of food options!" [](https://expedia.ca/Sheboygan-Hotels-Holiday-Inn-Manitowoc.h8038.Hotel-Information) ![Grandstay Residential Suites Hotel - Sheboygan](https://images.trvl-media.com/lodging/3000000/2010000/2005100/2005043/402d6f8a_y.jpg) ### Grandstay Residential Suites Hotel - Sheboygan 10/10 Excellent "The hotel is located in a nice part of town. Quiet, and a few shops, restaurants and parks nearby. The room was spacious and clean, and the bed was comfortable. We really enjoyed our stay here." [](https://expedia.ca/Sheboygan-Hotels-Grandstay-Residential-Suites-Hotel-Sheboygan.h2005043.Hotel-Information) ![The Osthoff Resort](https://images.trvl-media.com/lodging/1000000/200000/197900/197890/9c5f3d9b_y.jpg) ### The Osthoff Resort 10/10 Excellent "Everything was amazing!!! Can't wait to go back." [](https://expedia.ca/Sheboygan-Hotels-The-Osthoff-Resort.h197890.Hotel-Information) ![La Quinta Inn by Wyndham Sheboygan](https://images.trvl-media.com/lodging/1000000/40000/40000/39976/0c381b2f_y.jpg) ### La Quinta Inn by Wyndham Sheboygan 10/10 Excellent "Yes- everything was in great order and well kept. Breakfast was outstanding." [](https://expedia.ca/Sheboygan-Hotels-La-Quinta-Inn-By-Wyndham-Sheboygan.h39976.Hotel-Information) ![AmericInn by Wyndham Sheboygan](https://images.trvl-media.com/lodging/1000000/670000/663100/663055/ea3b9a85_y.jpg) ### AmericInn by Wyndham Sheboygan 10/10 Excellent "Yes" [](https://expedia.ca/Sheboygan-Hotels-AmericInn-By-Wyndham-Sheboygan.h663055.Hotel-Information) ![Holiday Inn Express Sheboygan-Kohler by IHG](https://images.trvl-media.com/lodging/1000000/50000/43200/43134/a3806c9c_y.jpg) ### Holiday Inn Express Sheboygan-Kohler by IHG 10/10 Excellent "Clean room. Very good breakfast. Great customer service." [](https://expedia.ca/Sheboygan-Hotels-Holiday-Inn-Express-Sheboygan-Kohler.h43134.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Cleveland? > [Shoreline Serenity - 2 Private Acres](https://www.expedia.ca/Cleveland-Hotels-NEW-Shoreline-Serenity.h112904087.Hotel-Information): Vacation home, 1-minute walk from Lake Michigan. Offers complimentary wireless internet access, a pool, and kitchens. [Insane luxury beachfront estate - complete with indoor pool, arcade and theater!](https://www.expedia.ca/Cleveland-Hotels-Insane-Luxury-Beachfront-Estate-Complete-With-Indoor-Pool.h90114463.Hotel-Information): Aparthotel, 14-minute walk from Lake Michigan. Offers daily, an indoor pool, and free self parking. [Stunning castle with working vineyard - the ultimate luxury VRBO property!](https://www.expedia.ca/Cleveland-Hotels-Stunning-Castle-With-Working-Vineyard-The-Ultimate-Luxury-VRBO-Property.h78390435.Hotel-Information): Features complimentary wired internet access, an indoor pool, and free self parking. [The American Club](https://www.expedia.ca/Sheboygan-Hotels-The-American-Club.h21295.Hotel-Information): Hotel, 1-minute walk from Lake Michigan. Features a private beach, an indoor pool, and cooked-to-order. [Grandstay Residential Suites Hotel - Sheboygan](https://www.expedia.ca/Sheboygan-Hotels-Grandstay-Residential-Suites-Hotel-Sheboygan.h2005043.Hotel-Information): Hotel, 6-minute walk from Lake Michigan. Offers a snack bar/deli, an indoor pool, and continental. ### What is there to see and do in Cleveland? > Explore places like Lake Michigan while you're in Cleveland. Take in the natural beauty with a stop at Dairyland Park. ### When is the best time to book a hotel with a pool in Cleveland? > Taking into account the local weather in Cleveland is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Cleveland are January, March, February, and October, with each month seeing an average of 7 inches of snowfall. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Blue Harbor Resort & Conference Center Water Park](https://www.expedia.ca/Blue-Harbor-Resort-Conference-Center-Water-Park-Hotels.0-l553248621532659437-0.Travel-Guide-Filter-Hotels) - [Manitowoc County Hotels](https://www.expedia.ca/Destinations-In-Manitowoc-County.d553248635976430460.Hotel-Destinations) - [Luxury Hotels in Sheboygan County](https://www.expedia.ca/Destinations-In-Sheboygan-County-Luxury-Hotel.0-0-d553248635976431805-tLuxuryHotel.Hotel-Filter-Destinations) - [Sheboygan County Hotels](https://www.expedia.ca/Destinations-In-Sheboygan-County.d553248635976431805.Hotel-Destinations) - [Hotels & Resorts for Couples in Wisconsin](https://www.expedia.ca/Destinations-In-Wisconsin-Couples-Resorts-Hotels.0-0-d251-tCouplesResortsHotels.Hotel-Filter-Destinations) - 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