--- title: "Sleepy Hollow Vacation Packages 2026 from $509 | Expedia" description: "Bundle Sleepy Hollow flight + hotel & save up to 100% off your flight with Expedia. Filter packages by price, amenities & location. FREE cancellation on select hotels." canonical: "https://www.expedia.com/Sleepy-Hollow.d3000435324.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-12T19:17:25Z --- # Sleepy Hollow Vacations from $353 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 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.com/Grand-Victoria-Casino-Elgin.d6065129.Vacation-Attraction), [Santas Village](https://www.expedia.com/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) and [NOW Arena](https://www.expedia.com/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. ## The Latest Sleepy Hollow Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A modern living room with a sofa, armchairs, and a coffee table. There are bookshelves and a decorative wall panel.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/7b445c7a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A tall, modern building with a glass facade and the name "Essen Sex Inn" on the top.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/d9eeaac7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 14 - Jan 18** ### [Le Méridien Essex Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-14/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=35130365&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.0/10** \- Wonderful (1,000 reviews) "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything." Reviewed November 3, 2026 Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$507~~](https://www.expedia.com/) **$353** per traveler found 1 day ago - ![An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A spacious indoor area with seating arrangements, large windows, and indoor plants.](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 23 - Jan 27** ### [The Emily Hotel + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-23/2027-01-27/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.2/10** \- Wonderful (1,359 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$1,183~~](https://www.expedia.com/) **$719** per traveler found 1 day ago - ![A modern living room with a large window overlooking a body of water, a tripod, and a sofa.](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 23 - Jan 27** ### [Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-23/2027-01-27/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=57651125&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.4/10** \- Exceptional (2,756 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$1,604~~](https://www.expedia.com/) **$1,045** per traveler found 1 day ago - ![A modern high-rise building with multiple balconies, large windows, and a city skyline in the background.](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/6b730d6f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A balcony with a city view, including a parking lot and a building labeled "Carnival."](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/dbb66963.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 23 - Jan 27** ### [Level Chicago Fulton Market + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-23/2027-01-27/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.2/10** \- Wonderful (609 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$948~~](https://www.expedia.com/) **$622** per traveler found 1 day ago - ![A rooftop pool area with lounge chairs and umbrellas, surrounded by buildings with 'Whole Foods Market' signage.](https://images.trvl-media.com/lodging/113000000/112870000/112868000/112867973/0bd05cf3.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern bedroom with a large bed, a nightstand, a lamp, and a view of a cityscape through large windows.](https://images.trvl-media.com/lodging/113000000/112870000/112868000/112867973/f4d721bd.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 23 - Jan 27** ### [Stay One Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-23/2027-01-27/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=112867973&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **8.6/10** \- Excellent (25 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$1,079~~](https://www.expedia.com/) **$759** per traveler found 1 day ago ## Where to stay near Sleepy Hollow Discover the charm of Sleepy Hollow, a family-friendly destination perfect for outdoor adventures and city exploration. Enjoy scenic parks and nearby attractions reminiscent of Sleepy Hollow, NY, while experiencing the warm atmosphere of Illinois' major cities. Ideal for families and romantic getaways, Sleepy Hollow offers delightful scenery and sunny weather. - [West Dundee](#) - [East Dundee](#) - [Carpentersville](#) - [Elgin](#) - [Schaumburg](#) ![A red brick building with a clock tower, a flag, and a blue handicap parking sign.](https://images.trvl-media.com/place/172781/9090f38f-fca8-4128-a7d9-b7c128de5465.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for West Dundee](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=172781) ### West Dundee For travelers seeking a memorable trip, West Dundee offers a delightful blend of entertainment and outdoor experiences just about 1 mile by car from Sleepy Hollow. Families will enjoy the thrills of Santa's Village, while sports enthusiasts can catch events at NOW Arena. With a nearby shopping mall center and the Schaumburg Convention Center for business needs, West Dundee is a smart choice for those wanting both leisure and convenience. Experience the charm of this vibrant city on your next getaway! [See properties](https://www.expedia.com/Hotel-Search?regionId=172781) ![A calm river surrounded by lush green trees and a clear blue sky.](https://images.trvl-media.com/place/77214/d89129f9-a5ee-44fb-a319-95026035539d.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for East Dundee](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=553248634983561217) ### East Dundee Experience the charm of East Dundee, an excellent hub for family travelers and weekend getaways who want a mix of entertainment and outdoor activities. This vibrant city offers easy access to attractions like Santa's Village, NOW Arena, and the Schaumburg Convention Center, perfect for creating lasting memories. Located about 1 mile by car from Sleepy Hollow, East Dundee provides a smart choice for your stay, combining delightful experiences with convenient access to local landmarks. [See properties](https://www.expedia.com/Hotel-Search?regionId=553248634983561217) [View properties in map for Carpentersville](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=3000346164) ### Carpentersville Make the most of your visit by staying in Carpentersville, a haven for family and budget travelers thanks to its array of outdoor activities and entertainment options. Visitors can enjoy the thrills of Santa's Village, catch events at the NOW Arena, or explore the nearby national state park. Located about 3 miles from Sleepy Hollow, Carpentersville is a smart choice for convenient access to local attractions, ensuring a delightful vacation experience. [See properties](https://www.expedia.com/Hotel-Search?regionId=3000346164) ![A river with waves, a bridge, and a large building with a tower.](https://images.trvl-media.com/place/7817/b9655744-b82e-478b-8efd-be542c5ed516.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Elgin](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=7817) ### Elgin Elgin stands out as a prime spot for travelers interested in a blend of city and outdoor experiences. With attractions like Santa's Village, NOW Arena, and Villa Olivia Country Club, visitors can enjoy fun-filled days and vibrant nightlife. Located about 5 miles by car from Sleepy Hollow, Elgin offers easy access to entertainment and leisure activities year-round. Choosing Elgin for your stay ensures a diverse experience, making it a smart choice for your vacation. [See properties](https://www.expedia.com/Hotel-Search?regionId=7817) ![A large park with a lake, surrounded by residential areas and a distant city skyline.](https://images.trvl-media.com/place/8107/fe2608bb-a5c4-4c8b-b6fa-6f0dfc3f7f61.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Schaumburg](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=8107) ### Schaumburg Travelers visiting the area often choose Schaumburg, especially families and couples seeking close proximity to vibrant attractions. This city offers a delightful mix of activities, from shopping at its expansive malls to enjoying events at the Schaumburg Convention Center and NOW Arena. With a variety of dining options and cultural experiences, Schaumburg serves as an ideal base for your vacation. Located about 12 miles from Sleepy Hollow, it presents a smart choice for your hotel stay, ensuring you’re never far from the excitement. [See properties](https://www.expedia.com/Hotel-Search?regionId=8107) ## Sleepy Hollow Hotel Deals ### [Elgin Inn](https://www.expedia.com/Elgin-Hotels-Elgin-Inn.h197433.Hotel-Information) ![A hotel room with a wooden desk, a chair, a desk lamp, a flat-screen TV, a microwave, and a cabinet.](https://images.trvl-media.com/lodging/1000000/200000/197500/197433/31d9bd0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 405 Airport Rd, Elgin, IL, 60123, US - Location: 2.1 mi from Sleepy Hollow - Star rating: 3/5 - Guest rating: 8/10 (Very good, 877 reviews) - Price: $80 nightly, $91 total, Nov 15 - Nov 16, Total with taxes and fees - Review: Good place ### [Best Western Plus Elgin - Chicago](https://www.expedia.com/West-Dundee-Hotels-Sonesta-Select-Chicago-Elgin-West-Dundee.h327433.Hotel-Information) ![A hotel with a modern design, featuring a covered entrance, multiple balconies, and a landscaped front yard.](https://images.trvl-media.com/lodging/1000000/330000/327500/327433/w3836h2558x4y3-1ebe1731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 2175 Marriott Dr, West Dundee, IL, 60118, US - Location: 1.7 mi from Sleepy Hollow - Star rating: 3/5 - Guest rating: 8.6/10 (Excellent, 1092 reviews) - Price: $93 nightly, $104 total, Nov 16 - Nov 17, Total with taxes and fees ### [Holiday Inn Chicago Northwest-Elgin by IHG](https://www.expedia.com/Elgin-Hotels-Holiday-Inn-Chicago-Northwest-Elgin.h151142.Hotel-Information) ![A Holiday Inn hotel with a modern design, featuring a large entrance and multiple floors.](https://images.trvl-media.com/lodging/1000000/160000/151200/151142/d11e7d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 495 Airport Rd, Elgin, IL, 60123, US - Location: 1.8 mi from Sleepy Hollow - Star rating: 3/5 - Guest rating: 9/10 (Wonderful, 1002 reviews) - Price: $132 nightly, $150 total, Dec 6 - Dec 7, Total with taxes and fees ### [Comfort Suites Elgin Northwest](https://www.expedia.com/Elgin-Hotels-Comfort-Suites-Elgin.h1522193.Hotel-Information) ![A spacious lobby with a seating area, a reception desk, and a large window providing a view of the outside.](https://images.trvl-media.com/lodging/2000000/1530000/1522200/1522193/e476c91e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 2480 Bushwood Drive, Elgin, IL, 60124, US - Location: 2 mi from Sleepy Hollow - Star rating: 2.5/5 - Guest rating: 8/10 (Very good, 1002 reviews) - Price: $103 nightly, $118 total, Dec 1 - Dec 2, Total with taxes and fees ### [Country Inn & Suites by Radisson, Elgin, IL](https://www.expedia.com/Elgin-Hotels-Country-Inn-Suites-By-Radisson.h565186.Hotel-Information) ![A Country Inn & Suites building with a dark exterior, multiple windows, and a covered entrance area.](https://images.trvl-media.com/lodging/1000000/570000/565200/565186/c00de4cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 2270 Point Blvd, Elgin, IL, 60123, US - Location: 2 mi from Sleepy Hollow - Star rating: 2.5/5 - Guest rating: 7.4/10 (Good, 1000 reviews) - Price: $72 nightly, $82 total, Dec 3 - Dec 4, Total with taxes and fees - Review: I didn’t like the fact that they lock their side doors at 10, ### [Quality Inn Elgin I-90](https://www.expedia.com/Elgin-Hotels-Quality-Inn-Elgin-I-90.h50596.Hotel-Information) ![A lobby with a tufted leather sofa, a glass coffee table with a vase of flowers, a framed cityscape picture on the wall, and a lamp on a side table.](https://images.trvl-media.com/lodging/1000000/60000/50600/50596/5bc39e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 500 Tollgate Rd, Elgin, IL, 60123, US - Location: 1.8 mi from Sleepy Hollow - Star rating: 2.5/5 - Guest rating: 7.6/10 (Good, 1000 reviews) - Price: $61 nightly, $69 total, Dec 3 - Dec 4, Total with taxes and fees ### [Holiday Inn Express And Suites Elgin Chicago Northwest by IHG](https://www.expedia.com/Elgin-Hotels-Holiday-Inn-Express-And-Suites-Elgin-Chicago-Northwest-By-Ihg.h118973463.Hotel-Information) ![A modern hotel lobby with a sofa, chairs, a desk, and a map mural on the wall.](https://images.trvl-media.com/lodging/119000000/118980000/118973500/118973463/52f74c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1755 Capital Street, Elgin, IL, 60124, US - Location: 2.4 mi from Sleepy Hollow - Star rating: 2.5/5 - Guest rating: 8.8/10 (Excellent, 68 reviews) - Price: $101 nightly, $115 total, Dec 1 - Dec 2, Total with taxes and fees ### [Sinclair Suites](https://www.expedia.com/West-Dundee-Hotels-Sinclair-Suites.h109851335.Hotel-Information) ![A hotel entrance with a wooden door, a staircase, and a tiled mat.](https://images.trvl-media.com/lodging/110000000/109860000/109851400/109851335/32c08881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 120 W Main St, West Dundee, IL, 60118, US - Location: 1.1 mi from Sleepy Hollow - Star rating: 2/5 - Guest rating: 10/10 (Exceptional, 28 reviews) - Price: $248 nightly, $278 total, Nov 29 - Nov 30, Total with taxes and fees - Review: Great stay! 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. [See all properties in Sleepy Hollow](https://www.expedia.com/Hotel-Search?startDate=2026-11-26&endDate=2026-11-27®ionId=3000435324&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Sleepy Hollow ### Things to do near Sleepy Hollow Sleepy Hollow, Illinois, is perfect for family-friendly vacations, offering a blend of outdoor activities and urban charm. Visitors can enjoy shopping at local centers and explore educational attractions. Key experiences include exciting tour packages, spooky fun, village visits, and seasonal events, ensuring a memorable getaway for all ages. **Shopping** For a great shopping experience in Sleepy Hollow, visit [Cabela's](https://www.expedia.com/Cabelas-Chicago.d553248635998039755.Vacation-Attraction), just 5 miles away, or explore the [Arboretum of South Barrington](https://www.expedia.com/Arboretum-Of-South-Barrington-Chicago.d6175734.Vacation-Attraction), 6 miles away, which offers a vibrant atmosphere. If you're up for a drive, check out the [Crystal Court Shopping Center](https://www.expedia.com/Crystal-Court-Shopping-Center-Crystal-Lake.d6183823.Vacation-Attraction), located 9 miles away, for more options. **Recreation** Experience the lush greens at [Randall Oaks Golf Club](https://www.expedia.com/Randall-Oaks-Golf-Club-West-Dundee.d553248635974846255.Vacation-Attraction), just 3 miles away, perfect for golf enthusiasts. Enjoy vibrant performances at [Hemmens Cultural Center](https://www.expedia.com/Hemmens-Cultural-Center-Elgin.d6247286.Vacation-Attraction), 4 miles from Sleepy Hollow, offering a mix of culture and entertainment. For relaxation, visit [Elgin Sports Complex](https://www.expedia.com/Elgin-Sports-Complex-Elgin.d553248635974846086.Vacation-Attraction), located 5 miles away, promoting wellness and tranquility. **Adventure** [Epic Air Trampoline Park](https://www.expedia.com/Epic-Air-Trampoline-Park-South-Elgin.d553248621532658549.Vacation-Attraction), located 8 miles from Sleepy Hollow, offers exhilarating bouncing fun for all ages with its vibrant atmosphere. For outdoor enthusiasts, [North Wall Rock Climbing](https://www.expedia.com/North-Wall-Rock-Climbing-Crystal-Lake.d553248621532659115.Vacation-Attraction), also 8 miles away, provides thrilling climbing challenges surrounded by nature. [Brunswick Zone XL](https://www.expedia.com/Brunswick-Zone-XL-Algonquin.d553248621532658559.Vacation-Attraction), 4 miles away, combines arcade games with family-friendly excitement. **Nightlife** Experience Sleepy Hollow's nightlife with cozy bars and local eateries. Enjoy live music at nearby venues and unwind at charming pubs. The atmosphere is relaxed, perfect for mingling with locals and savoring delightful drinks. Explore the nearby areas for more vibrant nightlife options under the stars. ### Find the best attractions near Sleepy Hollow Sleepy Hollow, Illinois, offers a delightful mix of family-friendly and outdoor activities, making it perfect for any vacation. Explore popular attractions like the Sleepy Hollow Cemetery and local parks, as well as event venues and nature reserves. Whether you're seeking cultural experiences or simply enjoying the great outdoors, Sleepy Hollow has something for everyone to enjoy. - **[Santa's Village: ](https://www.expedia.com/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction)** Located 2 miles from Sleepy Hollow, Santa's Village is a delightful theme park perfect for families. With whimsical rides, interactive attractions, and festive entertainment, it captures the holiday spirit year-round, ensuring joy for visitors of all ages. - **[NOW Arena: ](https://www.expedia.com/NOW-Arena-Chicago.d6192396.Vacation-Attraction)** Just 5 miles away, NOW Arena is a premier entertainment facility hosting a variety of events. From thrilling sports games to spectacular concerts, the arena offers a vibrant atmosphere perfect for family outings and memorable experiences. - **[Schaumburg Convention Center: ](https://www.expedia.com/Schaumburg-Convention-Center-Chicago.d6169684.Vacation-Attraction)** Situated 13 miles from Sleepy Hollow, this event venue is ideal for business travelers. With modern facilities and versatile spaces, it hosts conferences and events, making it a hub for professional gatherings and networking. ### Best time to go to Sleepy Hollow The best time to visit Sleepy Hollow is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain. ### Tips to save on your trip to Sleepy Hollow - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Sleepy Hollow. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Frequently Asked Questions ### Is Sleepy Hollow better suited for a beach vacation or a cultural trip? Sleepy Hollow is primarily an urban destination known for family-friendly attractions and outdoor activities. The village was developed to retain its rural charm, featuring several lakes like [Pewaukee Lake](https://www.expedia.com/Pewaukee-Lake.d6256701.Vacation-Attraction), about 3 miles from the center, which offer water-based recreation. A Sleepy Hollow vacation can include exploring parks and enjoying the natural setting. ### How can I save money on a Sleepy Hollow vacation package? When you bundle, you can save up to 30%\*. To save money on a Sleepy Hollow package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. \*Members only. Savings vary. ### What are the top things to do in Sleepy Hollow? A Sleepy Hollow vacation offers a mix of family fun, outdoor recreation, and unique experiences: Browse and book [things to do in Sleepy Hollow](https://www.expedia.com/Things-To-Do-In-Sleepy%20Hollow.d3000435324.Travel-Guide-Activities) on Expedia. ### Do you need to rent a car in Sleepy Hollow, or is public transport enough? For a Sleepy Hollow vacation package, renting a car is generally recommended for exploring the area. While Sleepy Hollow is an urban destination, its family-friendly attractions and outdoor activities are spread out. For instance, [Santa's Village](https://www.expedia.com/Santas-Village.d553248621532658557.Vacation-Attraction) is about 4 miles from the center, and [Alpine Valley Ski Resort](https://www.expedia.com/Alpine-Valley-Ski-Resort.d6333637.Vacation-Attraction) is about 14 miles away. A car provides the flexibility to visit these various sights and parks, such as [Nagawaukee County Park and Beach](https://www.expedia.com/Nagawaukee-County-Park-and-Beach.d6256720.Vacation-Attraction), about 8 miles away, at your own pace. Travelers booking Sleepy Hollow vacation packages with flights will find a rental car convenient for reaching their accommodations and exploring the wider region. ### Can I change or cancel my Sleepy Hollow vacation package if my plans change? Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with. ### Do One Key members get extra savings when booking Sleepy Hollow vacation packages? Yes, members who join our free [One Key™](https://www.expedia.com/welcome-one-key) travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals. ### Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages? Yes, with Expedia's Book Now, Pay Later option, powered by [Affirm](https://www.expedia.com/ega/lodging/625310), you can spread the cost of your Sleepy Hollow vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it. ### How do I find last-minute vacation packages to Sleepy Hollow? To find last-minute vacation packages to Sleepy Hollow, explore the [last-minute deals](https://www.expedia.com/lp/b/vacations/last-minute-deals) section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices. ### How does free cancellation work on Sleepy Hollow vacation packages? Free cancellation on a Sleepy Hollow vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia [help center](https://www.expedia.com/helpcenter) for further details. ### Is it cheaper to book a Sleepy Hollow vacation as a package or separately? Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Sleepy Hollow getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save. ### Why should I book my Sleepy Hollow vacation package with Expedia? Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence. ## Explore a world of travel with Expedia - [Packages](?equalTargetTab=tab-0) - [St. John Cantius Church](https://www.expedia.com/St-John-Cantius-Church-West-Town.d553248621555594880.Vacation-Attraction) - [Rookery](https://www.expedia.com/Rookery-Downtown-Chicago.d553248621533116543.Vacation-Attraction) - [Rainbow Falls Waterpark](https://www.expedia.com/Rainbow-Falls-Waterpark-Chicago.d6247247.Vacation-Attraction) - [The Salt Shed](https://www.expedia.com/The-Salt-Shed-West-Town.d797220453891923968.Vacation-Attraction) - [Defiant Theatre](https://www.expedia.com/Defiant-Theatre-Lakeview.d553248621555594837.Vacation-Attraction) - [Navy Pier](https://www.expedia.com/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) - [Richard J. Daley Center](https://www.expedia.com/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [Skydeck Ledge](https://www.expedia.com/Skydeck-Ledge-Downtown-Chicago.d6125597.Vacation-Attraction) - [Grace Abbott Homes Vacations](https://www.expedia.com/Grace-Abbott-Homes.d6132393.Destination-Travel-Guides) - [Illinois Centennial Memorial Column](https://www.expedia.com/Illinois-Centennial-Memorial-Column-Logan-Square.d553248621533116616.Vacation-Attraction) - [Our Lady of Lourdes Church](https://www.expedia.com/Our-Lady-Of-Lourdes-Church-Uptown.d553248621555594758.Vacation-Attraction) - [Shops at North Bridge](https://www.expedia.com/Shops-At-North-Bridge-Downtown-Chicago.d6227764.Vacation-Attraction) - [Hutchinson Street Historic District](https://www.expedia.com/Hutchinson-Street-Historic-District-Uptown.d553248621533116620.Vacation-Attraction) - [Graceland Cemetery](https://www.expedia.com/Graceland-Cemetery-Uptown.d553248621533116619.Vacation-Attraction) - [St Nicholas Ukrainian Catholic Cathedral](https://www.expedia.com/St-Nicholas-Ukrainian-Catholic-Cathedral-West-Town.d553248621533116547.Vacation-Attraction) - [Wicker Park Vacations](https://www.expedia.com/Wicker-Park.d6227639.Destination-Travel-Guides) - [Goodman Theater](https://www.expedia.com/Goodman-Theater-Downtown-Chicago.d6065127.Vacation-Attraction) - [Algonquin Historic Village Hall](https://www.expedia.com/Algonquin-Historic-Village-Hall-Algonquin.d6183408.Vacation-Attraction) - [Gorilla Tango Theatre](https://www.expedia.com/Gorilla-Tango-Theatre-Bucktown.d553248621555594877.Vacation-Attraction) - [Tribune Tower](https://www.expedia.com/Tribune-Tower-Downtown-Chicago.d6064075.Vacation-Attraction) - [St. Josaphat Church](https://www.expedia.com/St-Josaphat-Church-Lincoln-Park.d553248621555594853.Vacation-Attraction) - [Huntley Vacations](https://www.expedia.com/Huntley.d3000434334.Destination-Travel-Guides) - [Randall Oaks Golf Club](https://www.expedia.com/Randall-Oaks-Golf-Club-West-Dundee.d553248635974846255.Vacation-Attraction) - [Farm-In-The-Zoo](https://www.expedia.com/Farm-In-The-Zoo-Lincoln-Park.d553248621533116592.Vacation-Attraction) - [Hoffman Estates Vacations](https://www.expedia.com/Hoffman-Estates.d7602.Destination-Travel-Guides) - [Riviera Theatre](https://www.expedia.com/Riviera-Theatre-Uptown.d553248621555594761.Vacation-Attraction) - [Lincoln Park Vacations](https://www.expedia.com/Lincoln-Park.d6059328.Destination-Travel-Guides) - [Northalsted Vacations](https://www.expedia.com/Northalsted.d6175472.Destination-Travel-Guides) - [Fourth Presbyterian Church](https://www.expedia.com/Fourth-Presbyterian-Church-Downtown-Chicago.d553248621555594919.Vacation-Attraction) - [International Museum of Surgical Science](https://www.expedia.com/International-Museum-Of-Surgical-Science-Downtown-Chicago.d6065139.Vacation-Attraction) - [Picasso Statue](https://www.expedia.com/Picasso-Statue-Downtown-Chicago.d6069235.Vacation-Attraction) - [Santa's Village](https://www.expedia.com/Santas-Village-East-Dundee.d553248621532658557.Vacation-Attraction) - [Anna and Frederick Douglass Park](https://www.expedia.com/Anna-And-Frederick-Douglass-Park-Lawndale.d507384.Vacation-Attraction) - [The Catlow Theater](https://www.expedia.com/The-Catlow-Theater-Barrington.d553248621532658589.Vacation-Attraction) - [Henry Gerber House](https://www.expedia.com/Henry-Gerber-House-Lincoln-Park.d710247336870899712.Vacation-Attraction) - [Six Flags Great America](https://www.expedia.com/Six-Flags-Great-America-Chicago.d6023396.Vacation-Attraction) - [Elgin Vacations](https://www.expedia.com/Elgin.d7817.Destination-Travel-Guides) - [Holy Name Cathedral](https://www.expedia.com/Holy-Name-Cathedral-Downtown-Chicago.d6246831.Vacation-Attraction) - [Marina City](https://www.expedia.com/Marina-City-Downtown-Chicago.d553248621533116577.Vacation-Attraction) - [Chicago Place Mall](https://www.expedia.com/Chicago-Place-Mall-Downtown-Chicago.d6199336.Vacation-Attraction) - [Apollo Theater Chicago](https://www.expedia.com/Apollo-Theater-Chicago-Lincoln-Park.d6182966.Vacation-Attraction) - [South Pond](https://www.expedia.com/South-Pond-Lincoln-Park.d553248621555594864.Vacation-Attraction) - [Now Arena](https://www.expedia.com/NOW-Arena-Chicago.d6192396.Vacation-Attraction) - [Three Oaks Recreation Area](https://www.expedia.com/Three-Oaks-Recreation-Area-Crystal-Lake.d6183817.Vacation-Attraction) - [Cadillac Palace Theatre](https://www.expedia.com/Cadillac-Palace-Theatre-Downtown-Chicago.d6227645.Vacation-Attraction) - [Saint Joseph Hospital](https://www.expedia.com/Saint-Joseph-Hospital-Lakeview.d6182919.Vacation-Attraction) - [Grand Victoria Casino](https://www.expedia.com/Grand-Victoria-Casino-Elgin.d6065129.Vacation-Attraction) - [Monique Meloche Gallery](https://www.expedia.com/Monique-Meloche-Gallery-West-Town.d553248621533116552.Vacation-Attraction) - [Chicago Children's Museum](https://www.expedia.com/Chicago-Childrens-Museum-Downtown-Chicago.d6064033.Vacation-Attraction) - [Advocate Illinois Masonic Medical Center](https://www.expedia.com/Advocate-Illinois-Masonic-Medical-Center-Lakeview.d6182910.Vacation-Attraction) - [Louis A. Weiss Memorial Hospital](https://www.expedia.com/Louis-A-Weiss-Memorial-Hospital-Uptown.d6182913.Vacation-Attraction) - [900 North Michigan Shops](https://www.expedia.com/900-North-Michigan-Shops-Downtown-Chicago.d6199347.Vacation-Attraction) - [Cantigny Park](https://www.expedia.com/Cantigny-Park-Chicago.d737433382087806976.Vacation-Attraction) - [Raging Waves Waterpark](https://www.expedia.com/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) - [Wrigley Building](https://www.expedia.com/Wrigley-Building-Downtown-Chicago.d6064091.Vacation-Attraction) - [Lincoln Park](https://www.expedia.com/Lincoln-Park-Lincoln-Park.d507390.Vacation-Attraction) - [Villa Olivia Country Club](https://www.expedia.com/Villa-Olivia-Country-Club-Chicago.d6227556.Vacation-Attraction) - [Marshall Field Building](https://www.expedia.com/Marshall-Field-Building-Downtown-Chicago.d553248621533116570.Vacation-Attraction) - [St. Clements Church](https://www.expedia.com/St-Clements-Church-Lincoln-Park.d553248621555594832.Vacation-Attraction) - [Michigan Avenue](https://www.expedia.com/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) - [Heavenly Massage](https://www.expedia.com/Heavenly-Massage-Chicago.d553248621532658582.Vacation-Attraction) - [Chicago City Hall](https://www.expedia.com/Chicago-City-Hall-Downtown-Chicago.d6064035.Vacation-Attraction) - [Woodfield Mall](https://www.expedia.com/Woodfield-Mall-Chicago.d6064089.Vacation-Attraction) - [Merchandise Mart](https://www.expedia.com/Merchandise-Mart-Downtown-Chicago.d6069193.Vacation-Attraction) - [Cabela's](https://www.expedia.com/Cabelas-Chicago.d553248635998039755.Vacation-Attraction) - [Depaul University-Loop Campus](https://www.expedia.com/DePaul-University-Loop-Campus-Downtown-Chicago.d6227480.Vacation-Attraction) - [Elks Veterans Memorial](https://www.expedia.com/Elks-Veterans-Memorial-Lincoln-Park.d553248621555594833.Vacation-Attraction) - [Flat Iron Building](https://www.expedia.com/Flat-Iron-Building-West-Town.d553248621533116555.Vacation-Attraction) - [Epic Air Trampoline Park](https://www.expedia.com/Epic-Air-Trampoline-Park-South-Elgin.d553248621532658549.Vacation-Attraction) - [Chase Tower](https://www.expedia.com/Chase-Tower-Downtown-Chicago.d553248621555594882.Vacation-Attraction) - [Driehaus Museum](https://www.expedia.com/Driehaus-Museum-Downtown-Chicago.d6246825.Vacation-Attraction) - [Jane Addams' Hull-House Museum](https://www.expedia.com/Jane-Addams-Hull-House-Museum-Near-West-Side.d553248621555594808.Vacation-Attraction) - [Lakeview Vacations](https://www.expedia.com/Lakeview.d178166.Destination-Travel-Guides) - [Wrigley View Rooftop](https://www.expedia.com/Wrigley-View-Rooftop-Lakeview.d553248621555594755.Vacation-Attraction) - [Edgewater Vacations](https://www.expedia.com/Edgewater.d6132445.Destination-Travel-Guides) - [Humboldt Park](https://www.expedia.com/Humboldt-Park-West-Town.d507386.Vacation-Attraction) - [Legoland® Discovery Center](https://www.expedia.com/LEGOLAND-Discovery-Center-Chicago.d6169680.Vacation-Attraction) - [Depaul University-Lincoln Park](https://www.expedia.com/DePaul-University-Lincoln-Park-Lincoln-Park.d6154855.Vacation-Attraction) - [Roosevelt University](https://www.expedia.com/Roosevelt-University-Downtown-Chicago.d553248633992284624.Vacation-Attraction) - [Goose Island Vacations](https://www.expedia.com/Goose-Island.d6132420.Destination-Travel-Guides) - [Garfield Park](https://www.expedia.com/Garfield-Park-East-Garfield-Park.d507387.Vacation-Attraction) - [Barrington Vacations](https://www.expedia.com/Barrington.d55053.Destination-Travel-Guides) - [University of Illinois Chicago](https://www.expedia.com/University-Of-Illinois-Chicago-Near-West-Side.d6064083.Vacation-Attraction) - [Carbide and Carbon Building](https://www.expedia.com/Carbide-And-Carbon-Building-Downtown-Chicago.d553248621555594910.Vacation-Attraction) - [Magnificent Mile Vacations](https://www.expedia.com/Magnificent-Mile.d800025.Destination-Travel-Guides) - [Our Lady of Sorrows Basilica](https://www.expedia.com/Our-Lady-Of-Sorrows-Basilica-East-Garfield-Park.d6069231.Vacation-Attraction) - [Chicago Vacations](https://www.expedia.com/Chicago.d178248.Destination-Travel-Guides) - [Streamwood Vacations](https://www.expedia.com/Streamwood.d163045.Destination-Travel-Guides) - [Cooking & Hospitality Institute of Chicago](https://www.expedia.com/Cooking-Hospitality-Institute-Of-Chicago-Downtown-Chicago.d553248621555594847.Vacation-Attraction) - [Holy Trinity Russian Orthodox Cathedral](https://www.expedia.com/Holy-Trinity-Russian-Orthodox-Cathedral-West-Town.d553248621533116553.Vacation-Attraction) - [Armitage Avenue](https://www.expedia.com/Armitage-Avenue-Lincoln-Park.d6199842.Vacation-Attraction) - [Crystal Lake Vacations](https://www.expedia.com/Crystal-Lake.d7731.Destination-Travel-Guides) - [Algonquin Vacations](https://www.expedia.com/Algonquin.d601912.Destination-Travel-Guides) - [Hemmens Cultural Center](https://www.expedia.com/Hemmens-Cultural-Center-Elgin.d6247286.Vacation-Attraction) - [Arboretum of South Barrington](https://www.expedia.com/Arboretum-Of-South-Barrington-Chicago.d6175734.Vacation-Attraction) - [Briar Street Theatre](https://www.expedia.com/Briar-Street-Theatre-Lakeview.d6175150.Vacation-Attraction) - [St. Basil Greek Orthodox Church](https://www.expedia.com/St-Basil-Greek-Orthodox-Church-Near-West-Side.d553248621555594804.Vacation-Attraction) - [Vic Theatre](https://www.expedia.com/Vic-Theatre-Lakeview.d6182977.Vacation-Attraction) - [Depaul Art Museum](https://www.expedia.com/DePaul-Art-Museum-Lincoln-Park.d553248621533116617.Vacation-Attraction) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/Sleepy-Hollow.d3000435324.Destination-Travel-Guides id-ID: https://www.expedia.co.id/Sleepy-Hollow.d3000435324.Perjalanan de-AT: https://www.expedia.at/Sleepy-Hollow.d3000435324.Reise-Angebote-Staedtereisen es: https://www.expedia.com/es/Sleepy-Hollow.d3000435324.Guia-de-vacaciones en-IN: https://www.expedia.co.in/Sleepy-Hollow.d3000435324.Holidays-City-Breaks en-GB: https://www.expedia.co.uk/Sleepy-Hollow.d3000435324.Holidays-City-Breaks en-US: https://www.expedia.com/Sleepy-Hollow.d3000435324.Destination-Travel-Guides en-TW: https://www.expedia.com.tw/en/Sleepy-Hollow.d3000435324.Destination-Travel-Guides fr-FR: https://www.expedia.fr/Sleepy-Hollow.d3000435324.Reservation-Sejours-Voyages zh-CN: https://www.expedia.com/cn/Sleepy-Hollow.d3000435324.Travel nl-NL: https://www.expedia.nl/Sleepy-Hollow.d3000435324.Vakantie-Stedentrips en-KR: https://www.expedia.co.kr/en/Sleepy-Hollow.d3000435324.Destination-Travel-Guides es-MX: https://www.expedia.mx/Sleepy-Hollow.d3000435324.Guia-de-vacaciones sv-SE: https://www.expedia.se/Sleepy-Hollow.d3000435324.Resor de-CH: https://www.expedia.ch/Sleepy-Hollow.d3000435324.Reise-Angebote-Staedtereisen en-NZ: https://www.expedia.co.nz/Sleepy-Hollow.d3000435324.Destination-Travel-Guides de-DE: https://www.expedia.de/Sleepy-Hollow.d3000435324.Reise-Angebote-Staedtereisen en-SG: https://www.expedia.com.sg/Sleepy-Hollow.d3000435324.Destination-Travel-Guides ```