Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Sleepy Hollow

Paper towels
Just remodeled apartment close to airport and mall
Just remodeled apartment close to airport and mall
10.0 out of 10, Exceptional, (14)
"Location was close to airport, restaurants and shopping"
The price is HK$1,050
HK$1,989 total
includes taxes & fees
18 Oct - 19 Oct
Just remodeled apartment close to airport and mall
Living area
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
Fridge, microwave, oven, stovetop
Fox River/Chain of Lakes Waterfront Home with Hot Tub
Fox River/Chain of Lakes Waterfront Home with Hot Tub
10.0 out of 10, Exceptional, (37)
"Loved our stay, stocked kitchen, great backyard and big tub. "
Fox River/Chain of Lakes Waterfront Home with Hot Tub
A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.2 out of 10, Wonderful, (41)
"Very comfortable… enjoyed the property to the upmost.."
The price is HK$3,043
HK$9,809 total
includes taxes & fees
20 Oct - 21 Oct
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Smart TV, books
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
9.4 out of 10, Exceptional, (30)
"Our stay was great. Had an issue with the breaker but was able to get a hold of the host and fix the issue with no problems. "
The price is HK$778
HK$2,210 total
includes taxes & fees
28 Oct - 29 Oct
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Microwave, dishwasher, coffee/tea maker, toaster
Spacious open concept home w/ game room + firepit
Spacious open concept home w/ game room + firepit
9.8 out of 10, Exceptional, (73)
"Very spacious home, bedrooms good sized, really liked the game room to keep the kids occupied."
Spacious open concept home w/ game room + firepit
Smart TV
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
10.0 out of 10, Exceptional, (1)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
The price is HK$980
HK$1,631 total
includes taxes & fees
15 Oct - 16 Oct
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Smart TV
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
9.8 out of 10, Exceptional, (30)
"Property was well described. "
The price is HK$776
HK$2,109 total
includes taxes & fees
15 Oct - 16 Oct
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Terrace/patio
Chicago-burb -Medinah -1 King and 1 Queen beds
Chicago-burb -Medinah -1 King and 1 Queen beds
9.6 out of 10, Exceptional, (32)
"The property was very clean and comfortable!"
Chicago-burb -Medinah -1 King and 1 Queen beds
Living area
In-ground pool, private! In town location near it all. Updated, Clean!
In-ground pool, private! In town location near it all. Updated, Clean!
10.0 out of 10, Exceptional, (3)
"Accommodating hosts, lovely property and location. Great support for our family visit."
In-ground pool, private! In town location near it all. Updated, Clean!
Fridge, microwave, oven, stovetop
Spacious Ranch blocks away from downtown McHenry
Spacious Ranch blocks away from downtown McHenry
9.8 out of 10, Exceptional, (16)
"Very nice place and host is great "
The price is HK$1,750
HK$2,548 total
includes taxes & fees
16 Oct - 17 Oct
Spacious Ranch blocks away from downtown McHenry
Exterior
Historic home with easy access to Chicago
Historic home with easy access to Chicago
9.8 out of 10, Exceptional, (172)
"A truly memorable stay. I booked this home for a bridal party I was in and the home was perfect for all of us to connect together and relax in between wedding events. One of the best Vrbos I’ve stayed. Would love to come back "
Historic home with easy access to Chicago
Property grounds
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
9.0 out of 10, Wonderful, (4)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
The price is HK$1,634
HK$3,762 total
includes taxes & fees
11 Nov - 12 Nov
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Smart TV, books
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
2.0 star property
10.0 out of 10, Exceptional, (1)
"Super comfy for families and the nicest host. "
The price is HK$2,340
HK$3,053 total
includes taxes & fees
26 Oct - 27 Oct
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (51)
"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 HK$1,323
HK$2,416 total
includes taxes & fees
21 Oct - 22 Oct
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop
St. Charles Riverview Retreat
St. Charles Riverview Retreat
10.0 out of 10, Exceptional, (26)
"Very comfortable house and near downtown St Charles. We were only there 2 nights attending a family function. "
St. Charles Riverview Retreat
1 bedroom, desk, iron/ironing board, free WiFi
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
9.6 out of 10, Exceptional, (21)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
The price is HK$770
HK$2,053 total
includes taxes & fees
29 Oct - 30 Oct
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Outdoor banquet area
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
The price is HK$38,898
HK$85,830 total
includes taxes & fees
7 Nov - 8 Nov
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
Property grounds
"St Geneva" Private With River View! 7 min to the Q Center
"St Geneva" Private With River View! 7 min to the Q Center
10.0 out of 10, Exceptional, (82)
"The property was wonderful. It was so clean. Michael was a great host. He was a great communicator. I would stay there again when we go back to Illinois!"
"St Geneva" Private With River View! 7 min to the Q Center
Exterior
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
3.5 star property
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
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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Top Sleepy Hollow Hotel Reviews

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

10/10 Excellent
"Very cool place "
Nicholas 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

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:

  • View our selection of featured holiday rentals in Sleepy Hollow
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Look no further and take a look at our great range of rental properties 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?

Spacious Ranch blocks away from downtown McHenry : This holiday home rental outside of Sleepy Hollow offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

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.