Title: Book the Best Hotels with POOL in Sleepy Hollow in 2026 | Expedia.ca [Hotels in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Hotels.d3000435324.Travel-Guide-Hotels)[Vacation Rentals in Sleepy Hollow](https://expedia.ca/Sleepy-Hollow-Vacation-Rentals.d3000435324.Travel-Guide-VacationRentals)[Things to do in Sleepy Hollow](https://expedia.ca/Things-To-Do-In-Sleepy-Hollow.d3000435324.Travel-Guide-Activities)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d3000435324.Car-Rental-Guide)[Sleepy Hollow Vacation Packages](https://expedia.ca/Sleepy-Hollow.d3000435324.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 Sleepy Hollow, IL from CA $96 - ![](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 Sleepy Hollow Hotels with a Pool Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sleepy Hollow hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/70000/67700/67693/a101bbca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/67700/67693/dfcf724b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with premium channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/70000/67700/67693/f3160b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/70000/67700/67693/ccd7280f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago/Hoffman Estates [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoHoffman-Estates.h67693.Hotel-Information) Hoffman Estates 8.4/10 Very good (1001) "Good stay at a nice place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe CA $116 CA $131 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoHoffman-Estates.h67693.Hotel-Information) ![Indoor pool, open 7:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/20000/19951/6088c1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/20000/19951/28899350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/20000/19951/7546ae4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/20000/19951/053158d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago Nw Crystal Lk Conv Ctr by IHG [](https://www.expedia.ca/Crystal-Lake-Hotels-Holiday-Inn-Chicago-Nw-Crystal-Lk-Conv-Ctr.h19951.Hotel-Information) Crystal Lake 8.0/10 Very good (1001) "Nice place to stay, the pool is warm. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dulyer Catalina CA $138 CA $156 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Crystal-Lake-Hotels-Holiday-Inn-Chicago-Nw-Crystal-Lk-Conv-Ctr.h19951.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/480000/477000/476988/449e0a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed | Living area](https://images.trvl-media.com/lodging/1000000/480000/477000/476988/ca99089e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/480000/477000/476988/59c96f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/480000/477000/476988/9a3301ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn St. Charles [](https://www.expedia.ca/St-Charles-Hotels-Hilton-Garden-Inn-St-Charles.h476988.Hotel-Information) St. Charles 8.6/10 Excellent (769) "Room had a really great shower" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $120 CA $135 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/St-Charles-Hotels-Hilton-Garden-Inn-St-Charles.h476988.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/ec7ecb23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/981f8262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/908ca48d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/48659b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn McHenry [](https://www.expedia.ca/McHenry-Hotels-Hampton-Inn-McHenry.h911301.Hotel-Information) McHenry 9.0/10 Wonderful (879) "Everything was clean, and the staff was very polite. We enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $135 CA $149 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/McHenry-Hotels-Hampton-Inn-McHenry.h911301.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/330000/327500/327433/cc66c427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/330000/327500/327433/44a3f008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/330000/327500/327433/8cc9954a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/330000/327500/327433/a0a96e52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Elgin - Chicago [](https://www.expedia.ca/West-Dundee-Hotels-Sonesta-Select-Chicago-Elgin-West-Dundee.h327433.Hotel-Information) West Dundee 8.2/10 Very good (1002) "Clean and quiet. Good full breakfast from eggs and bacon to waffles to oats and pastries and fruit. Plenty of parking. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meredith CA $116 CA $130 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/West-Dundee-Hotels-Sonesta-Select-Chicago-Elgin-West-Dundee.h327433.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2230000/2223300/2223221/4d1d3210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2230000/2223300/2223221/605e776e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/3000000/2230000/2223300/2223221/ec931d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2230000/2223300/2223221/e4844b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Chicago West-Roselle by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-West-Roselle.h2223221.Hotel-Information) Roselle 8.0/10 Very good (1002) "It was an amazing stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zain Ul CA $109 CA $121 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-West-Roselle.h2223221.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/550000/548400/548375/e79dd128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/548400/548375/5245ab0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/548400/548375/4d0a7417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/550000/548400/548375/325a1bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Crystal Lake, IL [](https://www.expedia.ca/Crystal-Lake-Hotels-Country-Inn-Suites-By-Radisson.h548375.Hotel-Information) Crystal Lake 8.8/10 Excellent (1000) "Very nice pool and clean rooms . Pool and hot tub were excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JANET CA $136 CA $153 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Crystal-Lake-Hotels-Country-Inn-Suites-By-Radisson.h548375.Hotel-Information) ![Indoor pool, outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/338bbbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/1a475be9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/c603e0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/21c34d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eaglewood Resort and Spa [](https://www.expedia.ca/Chicago-Hotels-Eaglewood-Resort-And-Spa.h897168.Hotel-Information) Itasca 8.8/10 Excellent (1013) "Clean hotel, very friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherelle [](https://www.expedia.ca/Chicago-Hotels-Eaglewood-Resort-And-Spa.h897168.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/c7679662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/2322de6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/85c1a6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/aebf61bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn and Suites St Charles - West Chicago [](https://www.expedia.ca/St-Charles-Hotels-Quality-Inn-And-Suites-St-Charles-West-Chicago.h171194.Hotel-Information) St. Charles 8.2/10 Very good (1003) "Room was very clean and the staff was very friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carol CA $85 CA $96 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/St-Charles-Hotels-Quality-Inn-And-Suites-St-Charles-West-Chicago.h171194.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/800000/793600/793530/19171fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/800000/793600/793530/1dcd0ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/800000/793600/793530/aa34107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/800000/793600/793530/00788f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Crystal Lake - Algonquin [](https://www.expedia.ca/Crystal-Lake-Hotels-Comfort-Inn-Crystal-Lake-Algonquin.h793530.Hotel-Information) Crystal Lake 8.0/10 Very good (983) "Great breakfast! 😃" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $120 CA $136 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Crystal-Lake-Hotels-Comfort-Inn-Crystal-Lake-Algonquin.h793530.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=2025-12-26&endDate=2025-12-27®ionId=3000435324&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Sleepy Hollow Hotel Reviews ![Country Inn & Suites by Radisson, Schaumburg, IL](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/41e5f2c9_y.jpg) ### Country Inn & Suites by Radisson, Schaumburg, IL 10/10 Excellent "Room was very clean with kind and efficient check in services provided. " [](https://expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h120330.Hotel-Information) ![Hyatt Place Chicago/ Schaumburg](https://images.trvl-media.com/lodging/1000000/90000/82300/82257/df623816_y.jpg) ### Hyatt Place Chicago/ Schaumburg 10/10 Excellent "Amazing! " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-Schaumburg.h82257.Hotel-Information) ![Country Inn & Suites by Radisson, Elk Grove Village/Itasca](https://images.trvl-media.com/lodging/2000000/1200000/1195200/1195140/3b8d69af_y.jpg) ### Country Inn & Suites by Radisson, Elk Grove Village/Itasca 10/10 Excellent " Clean room, pool and Jacuzzi were nice, friendly staff, free breakfast was good, lots of free parking." [](https://expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h1195140.Hotel-Information) ![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/f931dcd0_y.jpg) ### Eaglewood Resort and Spa 10/10 Excellent "Clean hotel, very friendly staff " [](https://expedia.ca/Chicago-Hotels-Eaglewood-Resort-And-Spa.h897168.Hotel-Information) ![DoubleTree by Hilton Chicago - Arlington Heights](https://images.trvl-media.com/lodging/1000000/10000/9600/9551/a48ab1c2_y.jpg) ### DoubleTree by Hilton Chicago - Arlington Heights 10/10 Excellent "Exelente" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Arlington-Heights.h9551.Hotel-Information) ![Courtyard by Marriott Chicago Wood Dale](https://images.trvl-media.com/lodging/1000000/10000/3100/3034/400d8a7d_y.jpg) ### Courtyard by Marriott Chicago Wood Dale 10/10 Excellent "Room was clean. No problems." [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Wood-Dale.h3034.Hotel-Information) ![Hyatt Place Itasca](https://images.trvl-media.com/lodging/1000000/50000/42100/42029/97595919_y.jpg) ### Hyatt Place Itasca 10/10 Excellent "This was one of the e best experiences I’ve had at a hotel in a be try long time. Leah Castro and her team give EXCELLENT service. The next time I have to come to Chicago I’m staying here. Thank you Leah and team. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Itasca.h42029.Hotel-Information) ![DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove](https://images.trvl-media.com/lodging/1000000/10000/6600/6545/8dd24dc8_y.jpg) ### DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove 10/10 Excellent "Nest room Good staff Free parking Good value for money " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Wood-Dale-Elk-Grove.h6545.Hotel-Information) ![Wyndham Garden Schaumburg Chicago Northwest](https://images.trvl-media.com/lodging/1000000/30000/22500/22451/556a232c_y.jpg) ### Wyndham Garden Schaumburg Chicago Northwest 10/10 Excellent "Property is at very good locations...." [](https://expedia.ca/Chicago-Hotels-Wyndham-Garden-Schaumburg-Chicago-Northwest.h22451.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Sleepy Hollow? ### What is there to see and do in Sleepy Hollow? ### When is the best time to book a hotel with a pool in Sleepy Hollow? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Boutique Hotels in Algonquin ](https://www.expedia.ca/Algonquin-Hotels-Boutique-Hotel.0-0-d601912-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Algonquin ](https://www.expedia.ca/Algonquin-Hotels-Golf-Hotel.0-0-d601912-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Algonquin ](https://www.expedia.ca/Algonquin-Hotels-Hilton-Hotels.0-0-d601912--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Algonquin ](https://www.expedia.ca/Algonquin-Hotels-Hotels-With-Hot-Tubs.0-0-d601912-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - 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