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Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Sleepy Hollow holiday rentals

1 bedroom, desk, iron/ironing board, WiFi

1. 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)
"We were in town visiting family and it was the perfect spot to stay for a day or two. We loved that it was right above a local cafe (which was also fantastic by the way!!), and the check-in/out process was a breeze! Owner was very communicative, would definitely stay here again!"
United States
Adamm I.
The price is HK$1,515
HK$1,921 total
includes taxes & fees
16 Aug - 17 Aug
124 Lofts #3 - Downtown Dundee - Walk to Dining
Property grounds

2. Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (18 reviews)
"Clean, neat and very nicely designed and decorated. Host checked in multiple times with contact information and ensuring we had everything we needed."
United States
Brian
The price is HK$1,640
HK$2,078 total
includes taxes & fees
16 Aug - 17 Aug
Kildahl House - Boutique Farmhouse Suite #4
1 bedroom, desk, iron/ironing board, WiFi

3. 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)
"Great stay. The loft is situated in an area where it is easy to walk to interesting dining options and stroll the river walk."
United States
Angela D.
The price is HK$1,515
HK$1,921 total
includes taxes & fees
17 Aug - 18 Aug
124 Lofts #1 - Downtown Dundee - Walk to Dining
Property grounds

4. 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 HK$1,640
HK$2,086 total
includes taxes & fees
30 Aug - 31 Aug
Kildahl House - Boutique Farmhouse Suite #1
Property grounds

5. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Always a pleasure to stay here when visiting my son!"
United States
Jen C.
The price is HK$1,640
HK$2,086 total
includes taxes & fees
30 Aug - 31 Aug
Kildahl House - Boutique Farmhouse Suite #2
1 bedroom, desk, iron/ironing board, WiFi

6. 124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (22 reviews)
"Clean, cozy and a very nice central location for our trip around"
United States
Zachary K.
The price is HK$1,515
HK$1,921 total
includes taxes & fees
17 Aug - 18 Aug
124 Lofts #2 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

7. 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 HK$1,515
HK$1,929 total
includes taxes & fees
31 Aug - 1 Sept
124 Lofts #4 - Downtown Dundee - Walk to Dining
Property grounds

8. Kildahl House - Boutique Farmhouse Suite #3

Kildahl House - Boutique Farmhouse Suite #3
West Dundee
10.0 out of 10, Exceptional, (21 reviews)
"Everything was perfect! Great location and would stay there again. "
United States
EDWARD P.
The price is HK$1,640
HK$2,078 total
includes taxes & fees
16 Aug - 17 Aug
Kildahl House - Boutique Farmhouse Suite #3
Coffee/tea maker, fridge, microwave, oven

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

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
8.0 out of 10, Very good, (1 review)
"Everything was great except not enough pots n pans and ac unit is very loud."
United States
Phuong N.
The price is HK$1,074
HK$2,826 total
includes taxes & fees
8 Sept - 9 Sept
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Interior

10. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (48 reviews)
"Cozy home, perfect for a relaxting time away "
United States
Phoenicia
The price is HK$1,452
HK$2,054 total
includes taxes & fees
16 Aug - 17 Aug
Riverfront rental
Outdoor dining

11. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is HK$883
HK$1,501 total
includes taxes & fees
18 Aug - 19 Aug
Little Fox Cottage - A Cozy Riverview Getaway
2 bedrooms

12. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
King bed Crystal Lake Mchenry Cary Cozy
Exterior

13. 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 HK$1,609
HK$2,803 total
includes taxes & fees
1 Sept - 2 Sept
The Main Event Game House on the Huntley Square!
Interior

14. 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 HK$5,493
HK$7,601 total
includes taxes & fees
17 Aug - 18 Aug
Modern Suburban Oasis- 14 guest House. Family Friendly!
Paper towels, dining tables

15. 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 HK$1,681
HK$3,544 total
includes taxes & fees
1 Sept - 2 Sept
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Outdoor dining

16. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
8.0 out of 10, Very good, (1 review)
"Conveniently located near restaurants and downtown. Apartment was clean. Nicely decorated. Cute coffee station. Big table in dining area."
United States
Kim B.
The price is HK$1,123
HK$2,787 total
includes taxes & fees
16 Aug - 17 Aug
Spacious 3 Bedroom
Terrace/patio

17. - Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (44 reviews)
"Great place, well appointed, worked well for our needs!! Host was very responsive to any questions/requests. "
United States
Amy C.
The price is HK$1,059
HK$2,420 total
includes taxes & fees
16 Aug - 17 Aug
- Fully-Equipped Condo - King Bed - Massive yard -
Exterior

18. Near Chicago and O’Hare +Fenced yard + Game room!

Near Chicago and O’Hare +Fenced yard + Game room!
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
The price is HK$1,639
HK$3,541 total
includes taxes & fees
16 Aug - 17 Aug
Near Chicago and O’Hare +Fenced yard + Game room!
Exterior

19. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is HK$1,185
HK$2,229 total
includes taxes & fees
17 Aug - 18 Aug
The Tailor House
6 bedrooms, iron/ironing board, travel cot, WiFi

20. Minutes to Downtown Saint Charles, Cozy/Chic Home

Minutes to Downtown Saint Charles, Cozy/Chic Home
St. Charles
9.2 out of 10, Wonderful, (14 reviews)
"The house was perfect. Location was close to everything but on a quiet street in a really cute neighborhood. Our host was very communicative and helpful and everything was perfect and as expected based on the description. "
United States
Deborah G.
The price is HK$2,153
HK$4,710 total
includes taxes & fees
17 Aug - 18 Aug
Minutes to Downtown Saint Charles, Cozy/Chic Home
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

Hyatt Place Chicago/ Schaumburg

Hyatt Place Chicago/ Schaumburg

8/10 Good
"It's a clean hotel that has a decent breakfast."
Melissa 1-night trip
Posted 4 hours ago
Hyatt Place Chicago/ Schaumburg

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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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?

Breathtaking home close to Schaumburg, Chicago: This holiday home rental outside of Sleepy Hollow offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Hemmens Cultural Center and Grand Victoria Casino.

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.