Title: Sleepy Hollow Vacation Packages & Trips 2026 from CA $1,057 | 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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Sleepy Hollow Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Sleepy Hollow Vacation Entertainment, history, art and more … There's so much to experience with a Sleepy Hollow vacation package. And with the ability to customize your city getaway, it's guaranteed to be one you won't forget. Make your trip to Sleepy Hollow even more fun by going sightseeing. [Grand Victoria Casino](https://www.expedia.ca/Grand-Victoria-Casino-Elgin.d6065129.Vacation-Attraction), [Santas Village](https://www.expedia.ca/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) and [NOW Arena](https://www.expedia.ca/NOW-Arena-Chicago.d6192396.Vacation-Attraction) are among the top attractions worth exploring. Whatever your travel plans or budget, organizing your ultimate tailored Sleepy Hollow vacation is simple with Expedia. ## Top Sleepy Hollow Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Harbor Shores on Lake Geneva](https://images.trvl-media.com/lodging/1000000/10000/4700/4614/3a08fccc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harbor Shores on Lake Geneva CA $1,057 per person Jun 3 - Jun 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,318 reviews) During off season not as many activities Reviewed on Mar 16, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,236 per person Jun 7 - Jun 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Clean room, very nice front desk and great location Reviewed on Mar 26, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,087 per person Jun 7 - Jun 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) My only complaint was the sheets were rough and made my skin and my daughter's skin itchy.... maybe the detergent? Otherwise the room was very clean, breakfast was great, bag check was easy and valet was quick and not too pricey! All the staff were pleasant and professional! Reviewed on Mar 26, 2026 ![Lodge Geneva National](https://images.trvl-media.com/lodging/1000000/900000/893400/893361/c30b4670_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lodge Geneva National CA $1,404 per person Jun 3 - Jun 9 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,366 reviews) It was ok rooms were noisy can here everything in hall and in next room Reviewed on Mar 23, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $1,691 per person Jun 3 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) Staff was soooo friendly Reviewed on Mar 25, 2026 ## Ready to book your vacation to Sleepy Hollow? Choose your dates ## Sleepy Hollow Hotel Deals ![Comfort Inn & Suites Arlington Heights - Schaumburg](https://images.trvl-media.com/lodging/1000000/900000/894900/894864/d2adf0b5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Arlington Heights - Schaumburg 2112 S Arlington Heights Rd Arlington Heights IL CA $136 CA $152 total Apr 7 - Apr 8 includes taxes & fees 8.2/10 Very Good! (1,085 reviews) They apparently started remodeling this hotel but only did it halfway. The sink and floor of the bathroom were nice, but the shower was one of the worst I have seen - worn and nasty looking, and there was a place on the shower wall where the shampoo and conditioner had been ripped off and it had ... Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=894864&PinnedHotelID=894864&HadPinnedHotel=true®ionId=3000435324) ![Hyatt Place Itasca](https://images.trvl-media.com/lodging/1000000/50000/42100/42029/eeb89656_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Itasca 1150 North Arlington Heights Road Itasca IL Fully refundableReserve now, pay when you stay CA $151 CA $168 total Apr 21 - Apr 22 includes taxes & fees 8.8/10 Excellent! (1,001 reviews) Very nice place Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=21%2F04%2F2026&endDate=22%2F04%2F2026&selected=42029&PinnedHotelID=42029&HadPinnedHotel=true®ionId=3000435324) ![Quality Inn Schaumburg - Chicago near the Mall](https://images.trvl-media.com/lodging/1000000/10000/8500/8404/021474fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Schaumburg - Chicago near the Mall 600 North Martingale Rd Schaumburg IL Fully refundableReserve now, pay when you stay CA $110 CA $127 total Apr 15 - Apr 16 includes taxes & fees 8.6/10 Excellent! (1,002 reviews) Staff was excellent. Room and public areas where very clean. The breakfast was fine. The hotel itself is a bit dated. The heater/cooling device in the room was very loud. The chlorine smell was noticeable. Next time get a room away from the center of the building near the elevators. Reviewed on Mar 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=8404&PinnedHotelID=8404&HadPinnedHotel=true®ionId=3000435324) [See all 517 properties in Sleepy Hollow](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F03%2F2026&endDate=28%2F03%2F2026®ionId=3000435324) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app