Sleepy Hollow Holiday Rentals: Short-Term Accommodations for Rent

Q: 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.

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Holiday Rentals in Sleepy Hollow

Enjoy meals in this kitchen with a window and dining area nearby.

"Perfect for traveling as a family. Would definitely visit again "

Relax by the pool surrounded by lounge chairs and barbecue grills.

"The house was very clean and spacious. A lot of activities to do "

HK$17,759 total

includes taxes & fees

20 Jul - 21 Jul

Enjoy a drink at the hotel's bar, where a long counter and comfortable stools await.

"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!"

HK$1,625 total

includes taxes & fees

18 Jul - 19 Jul

Guests can enjoy a deck with a railing leading to a charming home.

"The property was very clean and comfortable!"

Relax in this inviting bedroom with a large bed, comfortable seating area, and a flat-screen TV.

"This is the perfect place to stay in Chicago "

HK$2,253 total

includes taxes & fees

17 Jul - 18 Jul

Sit and enjoy a meal in the charming outdoor seating area, surrounded by lush greenery and historic architecture.

"House is super clean, pictures are accurate. Would stay again! "

HK$2,284 total

includes taxes & fees

4 Aug - 5 Aug

Enjoy cooking in this well-lit kitchen with a black cooktop, dishwasher, and large window offering a view of the outdoors.

"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!"

HK$4,476 total

includes taxes & fees

17 Jul - 18 Jul

Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator and ample counter space.

"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."

HK$1,839 total

includes taxes & fees

22 Jul - 23 Jul

Relax on the patio with a sofa set, armchairs, and a small table, surrounded by a lush lawn and trees.

"Impressive AirBb our host really knock it out of the park..Thank you we will definitely be stay again.."

HK$1,691 total

includes taxes & fees

17 Jul - 18 Jul

Enjoy cooking in this well-lit kitchen with a large window and stainless steel appliances.

"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...

Enjoy cooking in this kitchen with a granite countertop, wooden cabinetry, and stainless steel appliances.

"Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! "

HK$5,089 total

includes taxes & fees

22 Jul - 23 Jul

Relax in a stylishly designed room with a comfortable bed, bedside table, and potted plant.

"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! "

HK$2,297 total

includes taxes & fees

5 Aug - 6 Aug

Equipped with a microwave, oven, and white cabinetry, this kitchen offers a clean and organized space for meal preparation.

"The place was just like it was described and it’s pictures. Clean, cozy, and in a nice quiet area. Would stay again! "

HK$2,512 total

includes taxes & fees

23 Jul - 24 Jul

Features a clean design with white cabinetry, hexagonal tile backsplash, and a dishwasher, stove, and ample counter space.

"Excellent place to stay with a large family gathering!!! "

Relax in this stylish living room with a comfortable sofa, armchair, and a side table.

"Good location, close to the beautiful city center of Geneva and train to Chicago."

HK$2,545 total

includes taxes & fees

20 Jul - 21 Jul

Relax by the pool surrounded by lush trees and a serene water view.

"Great host great home great trip"

Relax in this serene bedroom with a large bed against a wall of windows, a desk, chair, and floor lamp.

"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! "

Relax in this inviting living space with a comfortable sofa, flat-screen TV, and natural light pouring in through the window above the door.

"Perfect location Very clean house and lots of rooms"

Enjoy cooking in this well-equipped kitchen with a large island and oven.

"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."

HK$3,721 total

includes taxes & fees

12 Aug - 13 Aug

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Find out more about Sleepy Hollow

Search for holiday rentals in Sleepy Hollow on Expedia! You can easily find your home rentals, villas, holiday apartments in Sleepy Hollow using one of the methods below:

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Recent reviews of Sleepy Hollow properties

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

5/5 Excellent

"Great hotel "

A verified traveller stayed at DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

Posted 1 day ago

5/5 Excellent

"I arrived with a family of 5 for a weekend stay . While my mom and son were checking in their front desk person was very informative about the property (restaurant hours,gym hours ,do you need more than one key,what the property has to offer ,what’s close by ) etc however my front desk representative Bryan simply Che led me and asked was there anything else he could help me with 😳. I said yes ,I would like to know where things are located and what the hours are as well …like give me an introduction spill not just check me in and say thank you. Brian needs to work on his customer service skills…nice guy but just there to do the job is what it gave me . The hotel itself was fantastic all the way around . Nice ,very clean and spacious. The gym is open 24 hours which is a plus. I would definitely recommend this place and would stay there again for sure "

A verified traveller stayed at The Westin Chicago Northwest

Posted 2 days ago

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All accommodation types in Sleepy Hollow

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.

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Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

Charming 4 Bedroom home in the heart of Elgin

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

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

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

- Beautiful Condo - King Bed - Free Waffle Breakfast -

✽ Charming Cottage ✽ close to College/Town/Station

5BR Family Home + Backyard | LCP Collection

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

Just remodeled apartment close to airport and mall

Riverfront rental

Entire house/4bd 1bath/GlenEllyn

Family Heaven Retreat, 6 Bedroom, Sleep 16

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

Spacious open concept home w/ game room + firepit

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

Glen Ellyn Country Side Home

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

Minutes to Downtown Saint Charles, Cozy/Chic Home

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

Find out more about Sleepy Hollow

Recent reviews of Sleepy Hollow properties

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

The Westin Chicago Northwest

Comfort Inn & Suites Arlington Heights - Schaumburg

Courtyard by Marriott Chicago Wood Dale

Grand Royal Hotel O'Hare - Chicago

Eaglewood Resort and Spa

Hyatt Place Chicago/Hoffman Estates

Motel 6 Elk Grove Village, IL

DoubleTree by Hilton Chicago - Arlington Heights

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Frequently asked questions