Holiday Rentals in Sleepy Hollow

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Holiday Rentals in Sleepy Hollow

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (53)
"Location, cleanliness, accommodations, communication, ease of checking in and out were all perfect."
Breathtaking home close to Schaumburg, Chicago

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (59)
"Nice house, good location"
Spacious open concept home w/ game room + firepit

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (42)
"Everything was great! The host was very kind. Perfect for a short or long stay. It was real nice to have access to washing machine/dryer. Nice & clean. We highly recommend!"
The price is €259
includes taxes & fees
29 Apr - 30 Apr
✽ Charming Cottage ✽ close to College/Town/Station

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

6.0 out of 10, (1)
"Room clean, fitness room awful!! Have to request house keeping but they do not change sheets. Bar and restaurant bare minimum. They have a nice bar next to hotel(Not the-one located in the hotel) Would not stay again!"
The price is €108
includes taxes & fees
25 Apr - 26 Apr
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

9.4 out of 10, Exceptional, (33)
"The house was very clean and spacious. A lot of activities to do "
The price is €1,167
includes taxes & fees
28 Apr - 29 Apr
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Fox River Retreat

9.8 out of 10, Exceptional, (31)
"We enjoyed the comfort of a quiet house !!!"
Fox River Retreat

Cozy 3 bedroom river cottage w/ indoor fireplace

9.8 out of 10, Exceptional, (16)
"This was our second time here and was great as the first time. Its the prefect location for our event at Canlan Sports. We've already booked for next year even!Thanks!"
Cozy 3 bedroom river cottage w/ indoor fireplace

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

9.6 out of 10, Exceptional, (19)
"Well-stocked kitchen, towels and cleaning supplies. Hostess seemed to go the extra mile to help us feel welcomed with water, soda, coffee options and candy. Just slight confusion and panic on our part when they had our arrival date not until the next day, but it was remedied and all was well. "
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Great location-King beds-Kids playroom

10.0 out of 10, Exceptional, (24)
"Very clean and organized, very comfortable "
Great location-King beds-Kids playroom

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very good, (2)
"The property was perfect for hosting my birthday celebration of a group of 10. It provided adequate space and location. I was very pleased with the property."
The price is €355
includes taxes & fees
28 Apr - 29 Apr
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

Schaumburg Pool House

10.0 out of 10, Exceptional, (13)
"This is now a favorite for us whenever we need to travel to Chicago."
Schaumburg Pool House

Just remodeled apartment close to airport and mall

9.8 out of 10, Exceptional, (9)
"Ihor was very nice and the communication was good. He responded pretty quickly. The place was cute and clean. Neighborhood was good and pleasant. "
The price is €231
includes taxes & fees
29 Apr - 30 Apr
Just remodeled apartment close to airport and mall

Chicago-burb -Medinah -1 King and 1 Queen beds

9.6 out of 10, Exceptional, (19)
"Loved the mattresses and bedding. Great location and neighborhood for this basement unit. Heated floor in the bathroom was a real plus!"
Chicago-burb -Medinah -1 King and 1 Queen beds

3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay

8.0 out of 10, Very good, (1)
"Wonderful neighborhood! Comfortable beds! Great TV in the living room. Communication with host was fabulous. "
The price is €277
includes taxes & fees
28 Apr - 29 Apr
3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay

Spacious 3-bedroom apartment with AC,WiFi in charming Bartlett,free washer/dryer

The price is €241
includes taxes & fees
23 Apr - 24 Apr
Spacious 3-bedroom apartment with AC,WiFi in charming Bartlett,free washer/dryer

Riverfront rental with fun activities

10.0 out of 10, Exceptional, (25)
"The host is extremely personable and friendly. She went above and beyond in all aspects! We loved our little weekend getaway here-—no complaints! "
The price is €198
includes taxes & fees
24 Apr - 25 Apr
Riverfront rental with fun activities

The Carol Stream Casa - Luxury Large Home, 7 bds, 75" and 65" TVs, Workspace

2.0 star property
6.4 out of 10, (5)
"Exelente"
The Carol Stream Casa - Luxury Large Home, 7 bds, 75" and 65" TVs, Workspace

Game room+FirePit/Fenced yard/King Bed/Near O’Hare

10.0 out of 10, Exceptional, (25)
"Rented this spot because it was central to several family members living in surrounding cities. Had a great large backyard for the kids and nice deck for the adults. House was comfortable and and perfect for us."
Game room+FirePit/Fenced yard/King Bed/Near O’Hare

3BR House w/ Paradise Garden Oasis and private pool in the heart of Schaumburg

10.0 out of 10, Exceptional, (3)
"Great location, not far from some of the must sees in and out of the Chicago area. The backyard is awesome, it unfortunately snowed during our stay but during the summer months, you wouldn’t need to leave. The kids loved the themed rooms and all the Coca Cola things. Quiet neighborhood, owner was very responsive to questions, we would stay again!"
3BR House w/ Paradise Garden Oasis and private pool in the heart of Schaumburg

Fox River/Chain of Lakes Waterfront Home with Hot Tub

10.0 out of 10, Exceptional, (31)
"This home was spacious, well stocked, and had nicely manicured grounds. River view and sunsets were lovely. Our family had a fun Labor Day weekend experience!"
Fox River/Chain of Lakes Waterfront Home with Hot Tub
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.
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Other types of properties in Sleepy Hollow you may be interested in

Hyatt Regency Schaumburg Chicago

4.0 star property
8.6 out of 10, Excellent, (1041)
"Clean hotel and friendly staff"
The price is €119
includes taxes & fees
27 Apr - 28 Apr
Hyatt Regency Schaumburg Chicago

Hyatt Place Chicago/Hoffman Estates

3.0 star property
8.6 out of 10, Excellent, (1001)
"Was a grate stay and super helpful and nice staff! We arrived a day late due to our flight expidea was suppose to move out arrival time to Saturday from Friday they completely dropped the ball the hotel staff was super understanding and helped us fix the issue so we could have what became a fantastic stay. "
The price is €93
includes taxes & fees
11 May - 12 May
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Itasca

3.0 star property
8.8 out of 10, Excellent, (1002)
"Overall good stay. Very friendly and professional staff. Room was clean. Carpet condition could be improved."
The price is €91
includes taxes & fees
6 May - 7 May
Hyatt Place Itasca
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.

Frequently asked questions

Are there holiday rentals in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. Sleepy Hollow is known for its bars.

What are some of the best holiday rentals that Sleepy Hollow has to offer?

Breathtaking home close to Schaumburg, Chicago: This holiday home rental outside of Sleepy Hollow offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Santa's Village, or get outside and enjoy nature at Elgin Sports Complex. In the wider area, you’ll find Hemmens Cultural Center and Grand Victoria Casino.

What’s a holiday rental in Sleepy Hollow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sleepy Hollow. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.