Holiday Rentals in Sleepy Hollow

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Holiday Rentals in Sleepy Hollow

Charming 4 Bedroom home in the heart of Elgin

9.6 out of 10, Exceptional, (30)
"Perfect for traveling as a family. Would definitely visit again "
Charming 4 Bedroom home in the heart of Elgin

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

9.2 out of 10, Wonderful, (36)
"The house was very clean and spacious. A lot of activities to do "
The price is €1,520
includes taxes & fees
16 Jul - 17 Jul
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

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

5.2 out of 10, (5)
"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 €190
includes taxes & fees
11 Aug - 12 Aug
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

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

9.4 out of 10, Exceptional, (22)
"The property was very clean and comfortable!"
Chicago-burb -Medinah -1 King and 1 Queen beds

- Beautiful Condo - King Bed - Free Waffle Breakfast -

10.0 out of 10, Exceptional, (14)
"This is the perfect place to stay in Chicago "
The price is €278
includes taxes & fees
17 Jul - 18 Jul
- Beautiful Condo - King Bed - Free Waffle Breakfast -

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (45)
"House is super clean, pictures are accurate. Would stay again! "
The price is €263
includes taxes & fees
29 Jul - 30 Jul
✽ Charming Cottage ✽ close to College/Town/Station

5BR Family Home + Backyard | LCP Collection

9.0 out of 10, Wonderful, (2)
"I greatly enjoyed our stay at the property and the host was very gracious to us and communicated effectively. I would like to give the propefty a 5-star review, but unfortunately during our stay the beds lacked all bedding and the bathrooms only had 2 towels between them. But the host was very nice and supported us by delivering beddings. We appreciate the host and their communication in helping us have an amazing stay!"
The price is €500
includes taxes & fees
17 Jul - 18 Jul
5BR Family Home + Backyard | LCP Collection

8 Mi to Nature Center: Streamwood Gem w/ Yard!

10.0 out of 10, Exceptional, (1)
8 Mi to Nature Center: Streamwood Gem w/ Yard!

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (11)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
The price is €206
includes taxes & fees
16 Jul - 17 Jul
Just remodeled apartment close to airport and mall

Riverfront rental

9.8 out of 10, Exceptional, (30)
"Impressive AirBb our host really knock it out of the park..Thank you we will definitely be stay again.."
The price is €190
includes taxes & fees
22 Jul - 23 Jul
Riverfront rental

Entire house/4bd 1bath/GlenEllyn

2.0 star property
2.0 out of 10, (1)
"1. Hidden/unclear fees for "additional guests" though we never went over max amount of 10. 2. When first arrived at the house, both doors (outer door, and door access to the house) were wide open. Told host about this, she kept saying only the outer door was open. 3. One of us got locked in the only bathroom available at the house on the first night. Notified the host immediately. person had to climb out through a window. was told maintenance person was on their way. 2 hrs later, maintenance...
Entire house/4bd 1bath/GlenEllyn

Family Heaven Retreat, 6 Bedroom, Sleep 16

9.2 out of 10, Wonderful, (5)
"Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! "
The price is €570
includes taxes & fees
22 Jul - 23 Jul
Family Heaven Retreat, 6 Bedroom, Sleep 16

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

9.4 out of 10, Exceptional, (18)
"Spent three nights here. The place is absolutely immaculate and tastefully decorated. Neat and clean, everything you need, just like it states in VRBO. Owner was available for questions.Close to downtown with wonderful restaurants and shops. Easy walk and so fun! "
The price is €241
includes taxes & fees
12 Aug - 13 Aug
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

9.6 out of 10, Exceptional, (4)
"The place was just like it was described and it’s pictures. Clean, cozy, and in a nice quiet area. Would stay again! "
The price is €281
includes taxes & fees
17 Jul - 18 Jul
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (67)
"Excellent place to stay with a large family gathering!!! "
Spacious open concept home w/ game room + firepit

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

9.8 out of 10, Exceptional, (26)
"Good location, close to the beautiful city center of Geneva and train to Chicago."
The price is €285
includes taxes & fees
20 Jul - 21 Jul
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

Glen Ellyn Country Side Home

9.2 out of 10, Wonderful, (16)
"Great host great home great trip"
Glen Ellyn Country Side Home

-NEW- Blue Magnolia Cottage -3 King Beds- Luxury

10.0 out of 10, Exceptional, (1)
"We really enjoyed this property for our Christmas get-together. Very nice older home that has been well maintained. Beds were comfortable and the downstairs bathroom was perfect. The yoga room was a nice touch and was used as well. Very close to downtown and shopping and the large dining room table accommodated our family for meals and game playing. Host was very responsive to our questions as well. We would definitely recommend this home! "
-NEW- Blue Magnolia Cottage -3 King Beds- Luxury

Minutes to Downtown Saint Charles, Cozy/Chic Home

9.8 out of 10, Exceptional, (10)
"Perfect location Very clean house and lots of rooms"
Minutes to Downtown Saint Charles, Cozy/Chic Home

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 €418
includes taxes & fees
12 Aug - 13 Aug
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
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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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?

Chicago-burb -Medinah -1 King and 1 Queen beds: This holiday home rental outside of Sleepy Hollow offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Randall Oaks Golf Club and Hemmens Cultural Center.

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.