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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 25 - Mar 26](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2026-03-25&endDate=2026-03-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 26 - Mar 27](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2026-03-26&endDate=2026-03-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3000435324&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sleepy Hollow hotels with a pool ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/c603e0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/8359416a.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) ### Eaglewood Resort and Spa [](https://www.expedia.ca/Chicago-Hotels-Eaglewood-Resort-And-Spa.h897168.Hotel-Information) Itasca 8.8/10 Excellent (1,009 reviews) - Aquatic elegance meets relaxation at this resort's indoor pool sanctuary, featuring plush sun loungers and protective umbrellas. CA $138 CA $184 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Chicago-Hotels-Eaglewood-Resort-And-Spa.h897168.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/20000/19951/84cbeed9.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) ![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 8.2/10 Very good (1,000 reviews) - Dive into aquatic bliss at this modern hotel, where the indoor pool offers year-round relaxation amid plush sun loungers. CA $139 CA $157 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Crystal-Lake-Hotels-Holiday-Inn-Chicago-Nw-Crystal-Lk-Conv-Ctr.h19951.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/20700/20685/205d76ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/20700/20685/1525395b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/20700/20685/15c7f690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20700/20685/02427f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Woodstock IL [](https://www.expedia.ca/Woodstock-Hotels-Best-Western-Woodstock-Inn.h20685.Hotel-Information) Woodstock 8.0/10 Very good (1,000 reviews) - Float in indoor comfort at this serene hotel pool, where sun loungers invite poolside relaxation after exploring Woodstock. CA $111 CA $123 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Woodstock-Hotels-Best-Western-Woodstock-Inn.h20685.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/75000000/74550000/74544000/74543998/26cc968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/75000000/74550000/74544000/74543998/280e424e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/75000000/74550000/74544000/74543998/bd149ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Refrigerator & Microwave (Wet bar)](https://images.trvl-media.com/lodging/75000000/74550000/74544000/74543998/edbb4c6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Huntley Chicago [](https://www.expedia.ca/Hampton-Inn-By-Hilton-Huntley-Chicago.h74543998.Hotel-Information) Huntley 9.4/10 Exceptional (343 reviews) - Splash into relaxation at this art deco hotel with indoor pool and 24-hour fitness centre. CA $154 CA $178 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Hampton-Inn-By-Hilton-Huntley-Chicago.h74543998.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) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/c1dc3938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/048ed79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![49-inch TV with cable channels, Netflix, streaming services](https://images.trvl-media.com/lodging/1000000/920000/911400/911301/2858197c.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 (921 reviews) - Dive into an indoor pool sanctuary with sun loungers after exploring Moraine Hills State Park. CA $163 CA $181 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/McHenry-Hotels-Hampton-Inn-McHenry.h911301.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) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/d4f39f45.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/171200/171194/2322de6b.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 (1,000 reviews) - Unwind poolside at this modern hotel with a seasonal outdoor pool and lush green surroundings, perfect for summertime splashing. CA $93 CA $104 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/St-Charles-Hotels-Quality-Inn-And-Suites-St-Charles-West-Chicago.h171194.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/1000000/330000/327500/327433/8cc9954a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible, Bathtub (with Single Sofabed)](https://images.trvl-media.com/lodging/1000000/330000/327500/327433/aa1dbaba.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 (1,009 reviews) - Dive into serenity at this hotel's indoor oasis, complete with loungers for poolside relaxation. CA $121 CA $136 total includes taxes & fees Mar 28 - Mar 29 [](https://www.expedia.ca/West-Dundee-Hotels-Sonesta-Select-Chicago-Elgin-West-Dundee.h327433.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/800000/793000/792943/ad9ef059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/800000/793000/792943/f1a43a99.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/1000000/800000/793000/792943/83609ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/800000/793000/792943/05848e70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Geneva - West Chicago [](https://www.expedia.ca/Geneva-Hotels-Comfort-Inn-Suites-Geneva-West-Chicago.h792943.Hotel-Information) Geneva 8.8/10 Excellent (795 reviews) - Splash into year-round fun with an inviting indoor pool and soothing hot tub for post-workout relaxation. CA $143 CA $158 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Geneva-Hotels-Comfort-Inn-Suites-Geneva-West-Chicago.h792943.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/46000000/45350000/45348400/45348348/a3a804e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45350000/45348400/45348348/1011b456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45350000/45348400/45348348/7c44dd54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45350000/45348400/45348348/35faa11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Hoffman-Estates.h45348348.Hotel-Information) Hoffman Estates 9.2/10 Wonderful (697 reviews) - Make a splash at the indoor pool getaway just steps from NOW Arena, where refreshing swims meet 24-hour fitness. CA $117 CA $132 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Hoffman-Estates.h45348348.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 (791 reviews) - Revitalize with a refreshing swim in the indoor pool after exploring St. Charles, then energize at the 24-hour fitness centre. CA $123 CA $138 total includes taxes & fees Apr 4 - Apr 5 [](https://www.expedia.ca/St-Charles-Hotels-Hilton-Garden-Inn-St-Charles.h476988.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=2026-04-08&endDate=2026-04-09®ionId=3000435324&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Sleepy Hollow Breakfast included Hot tub 4 stars 5 stars Spa ## Top Sleepy Hollow Hotel Reviews ![Country Inn & Suites by Radisson, Schaumburg, IL](https://images.trvl-media.com/lodging/1000000/130000/120400/120330/eeebf839_y.jpg) ### Country Inn & Suites by Radisson, Schaumburg, IL 10/10 Excellent "Friendly staff and clean facilities " [](https://expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h120330.Hotel-Information) ![Country Inn & Suites by Radisson, Elk Grove Village/Itasca](https://images.trvl-media.com/lodging/2000000/1200000/1195200/1195140/367c607e_y.jpg) ### Country Inn & Suites by Radisson, Elk Grove Village/Itasca 10/10 Excellent "Great staff. Close to stores, restaurants, and other amenities." [](https://expedia.ca/Chicago-Hotels-Country-Inn-Suites-By-Radisson.h1195140.Hotel-Information) ![Quality Inn Schaumburg - Chicago near the Mall](https://images.trvl-media.com/lodging/1000000/10000/8500/8404/021474fc_y.jpg) ### Quality Inn Schaumburg - Chicago near the Mall 10/10 Excellent "The breakfast was great. The staff were polite " [](https://expedia.ca/Chicago-Hotels-Quality-Inn-Schaumburg-Chicago.h8404.Hotel-Information) ![DoubleTree by Hilton Libertyville - Mundelein](https://images.trvl-media.com/lodging/1000000/20000/14800/14710/w2374h2997x0y3-9205a137_y.jpg) ### DoubleTree by Hilton Libertyville - Mundelein 10/10 Excellent "The staff was extremely kind and helpful. They were very welcoming and it is clear they want you to have a good experience. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Libertyville-Mundelein.h14710.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 4/10 Poor "Staff were great. Room was mediocre. The carpets are stained, paint is chipping, part of the heat/AC unit was unattached and sitting adjacent. The AC was SO LOUD and rattled we turned it off completely. The room reeked of hideous disinfectant/deodorizer which gave me a headache, I had to open the window and stand in the doorway to get cross breeze to clear it out. The in-room “coffee” was gross brown water and the free lobby coffee wasn’t any better. When I asked the night crew for an extra blanket (see heat/AC unit above) the gentleman said he didn’t think they had any. No, the hotel was not sold out. They did manage to find a blanket so I didn’t freeze. As a Hilton property, I expect a lot better. There are several better options in the area than this. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Wood-Dale-Elk-Grove.h6545.Hotel-Information) ![Marriott Chicago Schaumburg](https://images.trvl-media.com/lodging/1000000/10000/800/744/abfce269_y.jpg) ### Marriott Chicago Schaumburg 10/10 Excellent "Yes" [](https://expedia.ca/Chicago-Hotels-Marriott-Chicago-Schaumburg.h744.Hotel-Information) ![Hampton Inn & Suites Chicago Schaumburg](https://images.trvl-media.com/lodging/16000000/15270000/15260900/15260803/dd0304df_y.jpg) ### Hampton Inn & Suites Chicago Schaumburg 10/10 Excellent "With all the hotels in the area this one is a real gem. Clean rooms, safe area, great breakfast and friendly staff. " [](https://expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Schaumburg.h15260803.Hotel-Information) ![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/c603e0d7_y.jpg) ### Eaglewood Resort and Spa 10/10 Excellent "Nice" [](https://expedia.ca/Chicago-Hotels-Eaglewood-Resort-And-Spa.h897168.Hotel-Information) ![Wyndham Garden Schaumburg Chicago Northwest](https://images.trvl-media.com/lodging/1000000/30000/22500/22451/126dc883_y.jpg) ### Wyndham Garden Schaumburg Chicago Northwest 6/10 Okay "No one at the front desk when we arrived. Only one elevator working. ALL the ice machines on every floor were out of order. Front desk told us to go to the adjacent restaurant to ask. They did not seem too thrilled. I’ve gone here before and it wasn’t that bad. It seemed more rundown than before. It wasn’t beachfront property to begin with but at least some upkeep would be nice. It seemed light and bright in the lobby but once you went to your room it was a sketchy looking hallway. Reno is certainly needed SOON! " [](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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