Holiday Homes in Sleepy Hollow

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Holiday Homes in Sleepy Hollow and around

Charming 4 Bedroom home in the heart of Elgin
Enjoy meals in this kitchen with a window and dining area nearby.

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
Chicago-burb -Medinah -1 King and 1 Queen beds
Guests can enjoy a deck with a railing leading to a charming home.

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
✽ Charming Cottage ✽ close to College/Town/Station
Sit and enjoy a meal in the charming outdoor seating area, surrounded by lush greenery and historic architecture.

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (46)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is €257
includes taxes & fees
4 Aug - 5 Aug
✽ Charming Cottage ✽ close to College/Town/Station
8 Mi to Nature Center: Streamwood Gem w/ Yard!
Exterior

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!
Geneva Retreat – 4BR, Big Yard, Near Downtown, Shops, and Riverwalk
Interior

Geneva Retreat – 4BR, Big Yard, Near Downtown, Shops, and Riverwalk

The price is €373
includes taxes & fees
21 Jul - 22 Jul
Geneva Retreat – 4BR, Big Yard, Near Downtown, Shops, and Riverwalk
5BR Family Home + Backyard | LCP Collection
Enjoy cooking in this well-lit kitchen with a black cooktop, dishwasher, and large window offering a view of the outdoors.

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 €701
includes taxes & fees
5 Aug - 6 Aug
5BR Family Home + Backyard | LCP Collection
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Relax by the pool surrounded by lounge chairs and barbecue grills.

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

9.2 out of 10, Wonderful, (37)
"The house was very clean and spacious. A lot of activities to do "
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Riverfront rental
Relax on the patio with a sofa set, armchairs, and a small table, surrounded by a lush lawn and trees.

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 €195
includes taxes & fees
22 Jul - 23 Jul
Riverfront rental
Family Heaven Retreat, 6 Bedroom, Sleep 16
Enjoy cooking in this kitchen with a granite countertop, wooden cabinetry, and stainless steel appliances.

Family Heaven Retreat, 6 Bedroom, Sleep 16

9.4 out of 10, Exceptional, (6)
"Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! "
The price is €573
includes taxes & fees
22 Jul - 23 Jul
Family Heaven Retreat, 6 Bedroom, Sleep 16
Spacious open concept home w/ game room + firepit
Features a clean design with white cabinetry, hexagonal tile backsplash, and a dishwasher, stove, and ample counter space.

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (67)
"Nice house, good location"
Spacious open concept home w/ game room + firepit
Glen Ellyn Country Side Home
Relax by the pool surrounded by lush trees and a serene water view.

Glen Ellyn Country Side Home

9.2 out of 10, Wonderful, (16)
"Great host great home great trip"
Glen Ellyn Country Side Home
Minutes to Downtown Saint Charles, Cozy/Chic 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.

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
Near Chicago&O’Hare/King Bed/WiFi+Game room
Fully equipped kitchen with microwave, gas range, and dishwasher.

Near Chicago&O’Hare/King Bed/WiFi+Game room

10.0 out of 10, Exceptional, (27)
"Good location and easy check in"
Near Chicago&O’Hare/King Bed/WiFi+Game room
Spacious 4BR Home with Game Room - LCP Collection
Relax in this stylish living room with a sofa, armchairs, and a flat-screen TV.

Spacious 4BR Home with Game Room - LCP Collection

10.0 out of 10, Exceptional, (5)
"Great Location and spacious with four bedrooms. Worked well with three adult children."
The price is €749
includes taxes & fees
18 Aug - 19 Aug
Spacious 4BR Home with Game Room - LCP Collection
Charming 3-bedroom house in Lake Zurich with AC, fitness room, WiFi
Enjoy cooking in this well-lit kitchen with a central island, sink, and convenient appliances.

Charming 3-bedroom house in Lake Zurich with AC, fitness room, WiFi

10.0 out of 10, Exceptional, (1)
"The property was good. it has a plethora of books, antiques and comfort. Although it is an older home it was comfortable, just watch your head in the upstairs bedrooms. "
Charming 3-bedroom house in Lake Zurich with AC, fitness room, WiFi
Stylish Escape/Game Room/4 Brs
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, set against a clean, minimalist backdrop.

Stylish Escape/Game Room/4 Brs

10.0 out of 10, Exceptional, (6)
"This was a wonderful house . very clean and organized . Will definitely stay here again. "
Stylish Escape/Game Room/4 Brs
3BR with Gameroom, Nintendo, Wi-Fi, Kids Fun Room
Relax in this inviting living space, featuring a comfortable sofa, bookshelf, and piano.

3BR with Gameroom, Nintendo, Wi-Fi, Kids Fun Room

10.0 out of 10, Exceptional, (2)
"Our family had to make a short notice trip to Chicago for a few nights and found this property. It was exactly as advertised. It was a great fit for a family if you’re preferring space over a hotel room."
3BR with Gameroom, Nintendo, Wi-Fi, Kids Fun Room
Chic hotel with WiFi, fitness room, AC in lovely Schaumburg
Relax in comfort with a large bed, desk, and TV.

Chic hotel with WiFi, fitness room, AC in lovely Schaumburg

The price is €126
includes taxes & fees
21 Jul - 22 Jul
Chic hotel with WiFi, fitness room, AC in lovely Schaumburg
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Enjoy cooking in this well-equipped kitchen with a large island and oven.

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

8.0 out of 10, Very good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
The price is €367
includes taxes & fees
21 Jul - 22 Jul
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi
Elegant New Home Near Lakes - Relax & Unwind!
Relax in this stylish living room with a sofa, ceiling fan, and sliding glass door leading to a balcony.

Elegant New Home Near Lakes - Relax & Unwind!

10.0 out of 10, Exceptional, (5)
"Beautiful condo close to Wonder Lake. I would recommend this property to everyone."
The price is €401
includes taxes & fees
28 Jul - 29 Jul
Elegant New Home Near Lakes - Relax & Unwind!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sleepy Hollow Hotel Reviews

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

10/10 Excellent
"At the very last minute I found out that I had to get a hotel. So I chose the cheapest one that was close by and that was a horrible decision. The very next day I went to Comfort inn and it was such a relief and the smell of the place was great. The workers there were great from the housekeeping staff to the front desk person. "
Chasidy R. 2-night trip
Posted 7 hours ago
Comfort Inn & Suites Arlington Heights - Schaumburg