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Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

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Places to Visit in Sleepy Hollow

Itinerary need filling up? Sleepy Hollow holiday all arranged but unsure what to expect when you get there? Let us make it easy for you.

Itching to go outside and have a little fun? The wider region has some wonderful activities for you to try, such as mountain biking. Still have time to spare? If you're eager for even more, grab the chance to go rock climbing as well.

Sleepy Hollow Accommodation

While it can be difficult to locate accommodation in central Sleepy Hollow, there are no less than 24 properties in the surrounding areas. Organising cheap holidays and luxury getaways is simple with Expedia.

If you're having trouble finding a place to stay, be sure to have a look at the Harvey House Bed & Breakfast (107 South Scoville Avenue) and the Bishops Hall (605 Iowa Street).

Nearest Airports to Sleepy Hollow

Trying to discover how to make the trek from Midway International Airport (MDW) to Sleepy Hollow? After you have grabbed your bags from luggage claim, you'll be 2 miles to the south of the main streets.


Sleepy Hollow Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Top Sleepy Hollow Hotel & Accommodation Deals

See all 1,796 properties in Sleepy Hollow
LondonHouse Chicago, Curio Collection by Hilton NZ$159
Reviewed on 9 Jul. 2020
See details
 
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive, Chicago, IL
     
    4.6 of 5
    4.5 out of 5.0 Stars

    Being on high floors and the elevator was on time.

    Sofitel Chicago Magnificent Mile NZ$338
    Reviewed on 10 Jul. 2020
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    Sofitel Chicago Magnificent Mile

    Sofitel Chicago Magnificent Mile

    20 E Chestnut St, Chicago, IL
       
      4.6 of 5
      4.5 out of 5.0 Stars

      Great clean and safe

      The Godfrey Hotel Chicago NZ$242
      Reviewed on 1 Jul. 2020
      See details
       
      The Godfrey Hotel Chicago

      The Godfrey Hotel Chicago

      127 West Huron, at LaSalle, Chicago, IL
         
        4.3 of 5
        4.5 out of 5.0 Stars

        Overall pleasing experience, I would not recommend you bring children if you have them even though they say all are welcome. Great traveling distance to downtown attractions. Great views of the sky line. The rooftop is bar far one of my favorites in the city. Would recommend will travel back there ...

        Kinzie Hotel NZ$190
        Reviewed on 8 Jul. 2020
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        Kinzie Hotel

        Kinzie Hotel

        20 W Kinzie St, Chicago, IL
           
          4.5 of 5
          4.0 out of 5.0 Stars

          Great location, friendly staff. So many great food options nearby and the Riverwalk.

          Best Western Grant Park Hotel NZ$102
          Reviewed on 6 Jul. 2020
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          Best Western Grant Park Hotel

          Best Western Grant Park Hotel

          1100 S Michigan Ave, Chicago, IL
             
            4.1 of 5
            2.5 out of 5.0 Stars

            The location was perfect. The staff was friendly and the room was good.

            The Whitehall Hotel NZ$158
            Reviewed on 8 Jul. 2020
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            The Whitehall Hotel

            The Whitehall Hotel

            105 E Delaware Pl, Chicago, IL
               
              4.1 of 5
              4.0 out of 5.0 Stars

              Everything was great. The room didn't have coffee maker and microwave

              Radisson Blu Aqua Hotel Chicago NZ$333
              Reviewed on 9 Jul. 2020
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              Radisson Blu Aqua Hotel Chicago

              Radisson Blu Aqua Hotel Chicago

              221 N Columbus Dr, Chicago, IL
                 
                4.4 of 5
                4.5 out of 5.0 Stars

                Beautiful views and updated amenities. Kind and welcoming staff.

                Viceroy Chicago NZ$402
                Reviewed on 8 Jul. 2020
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                Viceroy Chicago

                Viceroy Chicago

                1118 North State Street, Chicago, IL
                   
                  4.8 of 5
                  4.5 out of 5.0 Stars

                  The hotel is nice and in a fun area of Chicago. The room was decently clean, not spotless, and the carpet was stained. I was disappointed in the check-in, however. I booked this hotel because of the VIP perks and my Expedia gold status; it would allow for an upgraded room or some other perk. The ...