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Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Sleepy Hollow vacation rentals

Property grounds

1. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (18 reviews)
"Always a pleasure to stay here when visiting my son!"
United States
Jen C.
The price is ￥32,788
￥41,543 total
includes taxes & fees
Sep 21 - Sep 22
Kildahl House - Boutique Farmhouse Suite #2
Property grounds

2. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (17 reviews)
"This is a lovely place to call “home base” while visiting Chicago and surrounding communities. Comfortable, clean, quiet and nicely decorated. My little dogs even had a welcome basket! I wish I could have stayed a bit longer"
United States
Thea
The price is ￥32,788
￥41,211 total
includes taxes & fees
Oct 4 - Oct 5
Kildahl House - Boutique Farmhouse Suite #1
1 bedroom, desk, iron/ironing board, WiFi

3. 124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (28 reviews)
"Lovely stay! Great location!"
United States
David K.
The price is ￥30,278
￥38,400 total
includes taxes & fees
Sep 21 - Sep 22
124 Lofts #3 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

4. 124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is ￥30,278
￥38,400 total
includes taxes & fees
Sep 21 - Sep 22
124 Lofts #1 - Downtown Dundee - Walk to Dining
Coffee/tea maker, fridge, microwave, oven

5. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
9.0 out of 10, Wonderful, (2 reviews)
"Great place"
United States
Sthendall M.
The price is ￥21,461
￥55,664 total
includes taxes & fees
Oct 5 - Oct 6
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Property grounds

6. Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (19 reviews)
"We were in town for two granddaughters high school graduations and stayed eight days at the Kildahl House. It is an amazing place to stay with comforts of home. Furnishings were tastefully done, climate easily controlled and the bed was so comfortable. We will be staying here again!"
United States
Robert W.
The price is ￥32,788
￥41,543 total
includes taxes & fees
Sep 21 - Sep 22
Kildahl House - Boutique Farmhouse Suite #4
Property grounds

7. Kildahl House - Boutique Farmhouse Suite #3

Kildahl House - Boutique Farmhouse Suite #3
West Dundee
10.0 out of 10, Exceptional, (22 reviews)
"We had a really nice stay. The place was clean and quiet. We walked around the river in the evening with our 2 dogs. Lots of restaurants in walking distance. Would stay again if ever back in the area. Thank you!!"
United States
Jennifer W.
The price is ￥32,788
￥41,211 total
includes taxes & fees
Sep 27 - Sep 28
Kildahl House - Boutique Farmhouse Suite #3
1 bedroom, desk, iron/ironing board, WiFi

8. 124 Lofts #4 - Downtown Dundee - Walk to Dining

124 Lofts #4 - Downtown Dundee - Walk to Dining
West Dundee
9.8 out of 10, Exceptional, (20 reviews)
"Awesome loft. Perfect for an overnight stay. Convenient parking and lots of restaurants to choose from."
United States
Shannon
The price is ￥30,278
￥38,400 total
includes taxes & fees
Sep 21 - Sep 22
124 Lofts #4 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

9. 124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (23 reviews)
"Clean, cozy and a very nice central location for our trip around"
United States
Zachary K.
The price is ￥30,278
￥38,400 total
includes taxes & fees
Sep 21 - Sep 22
124 Lofts #2 - Downtown Dundee - Walk to Dining
Interior

10. 1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio

1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
Elgin
8.4 out of 10, Very good, (5 reviews)
"Property was amazing had everything you could need or want for a trip."
United States
Tonya K.
The price is ￥26,042
￥87,288 total
includes taxes & fees
Sep 21 - Sep 22
1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
House (3 Bedrooms) | Interior

11. 1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio

1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
3.0 star property
Elgin
The price is ￥33,415
￥92,774 total
includes taxes & fees
Sep 21 - Sep 22
1 Mi to Dtwn Elgin: Dutch Colonial w/ Lovely Patio
Interior

12. Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
Elgin
10.0 out of 10, Exceptional, (24 reviews)
"Very convenient and super clean stay. Exactly the kind of place we were looking for. Stayed for a work trip outside of Chicago. "
United States
Jennifer D.
The price is ￥25,258
￥64,580 total
includes taxes & fees
Oct 6 - Oct 7
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
Interior

13. Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
6.0 out of 10, (2 reviews)
The price is ￥109,816
￥151,963 total
includes taxes & fees
Sep 21 - Sep 22
Modern Suburban Oasis- 14 guest House. Family Friendly!
Interior

14. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
The price is ￥37,952
￥96,641 total
includes taxes & fees
Sep 22 - Sep 23
Waterfront - Private Dock - Two Suites
Property grounds

15. Perfect Family Getaway: Spacious 5BR Home in Barrington

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is ￥117,660
￥549,309 total
includes taxes & fees
Sep 21 - Sep 22
Perfect Family Getaway: Spacious 5BR Home in Barrington
Exterior

16. Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
Barrington
The price is ￥423,576
￥913,332 total
includes taxes & fees
Oct 3 - Oct 4
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
Interior

17. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (50 reviews)
"Incredible host and property."
United States
John V.
The price is ￥27,454
￥40,734 total
includes taxes & fees
Sep 21 - Sep 22
Riverfront rental
Exterior

18. The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is ￥19,453
￥40,567 total
includes taxes & fees
Oct 1 - Oct 2
The Main Event Game House on the Huntley Square!
Outdoor dining

19. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (19 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is ￥21,179
￥33,751 total
includes taxes & fees
Sep 28 - Sep 29
Little Fox Cottage - A Cozy Riverview Getaway
Paper towels, dining table

20. PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
streamwood
10.0 out of 10, Exceptional, (2 reviews)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is ￥27,509
￥61,315 total
includes taxes & fees
Oct 4 - Oct 5
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast 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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Top Sleepy Hollow Hotel Reviews

Best Western Plus Elgin - Chicago

Best Western Plus Elgin - Chicago

10/10 Excellent
"Great stay - would definitely stay again."
Lori 2-night trip
Posted 1 day ago
Best Western Plus Elgin - Chicago
Comfort Inn Chicago Schaumburg - O'Hare Airport

Comfort Inn Chicago Schaumburg - O'Hare Airport

10/10 Excellent
"Beds were very comfortable breakfast was good staff amazing."
Sonia N 5-night trip
Posted 1 day ago
Comfort Inn Chicago Schaumburg - O'Hare Airport

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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Frequently asked questions

Are there vacation rentals in Sleepy Hollow?

Yes, we offer vacation rentals near popular local attractions in Sleepy Hollow, or you can go with a secluded option if you want a relaxing place to stay. Sleepy Hollow is known for its bars.

What's the top vacation rental that Sleepy Hollow has to offer?

Pet Friendly, Near O’Hare, Fenced in, Cheerful Frida & Diego Home, up to 6 ppl: This vacation home rental outside of Sleepy Hollow offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games 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 larger area, you’ll find Hemmens Cultural Center and Grand Victoria Casino.

What’s a vacation rental in Sleepy Hollow like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Sleepy Hollow. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.