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Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Sleepy Hollow holiday rentals

A wicker tray with a pitcher and glasses on a wooden table on a porch.

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 HK$1,640
HK$2,061 total
includes taxes & fees
30 Sept - 1 Oct
Kildahl House - Boutique Farmhouse Suite #2
A room with a bed, a desk, a chair, a sofa, and a lamp.

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

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (24 reviews)
"Clean, cozy and a very nice central location for our trip around"
United States
Zachary K.
The price is HK$1,514
HK$1,862 total
includes taxes & fees
4 Oct - 5 Oct
124 Lofts #2 - Downtown Dundee - Walk to Dining
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

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)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is HK$1,514
HK$1,904 total
includes taxes & fees
30 Sept - 1 Oct
124 Lofts #1 - Downtown Dundee - Walk to Dining
A wicker tray with a pitcher and glasses on a wooden table on a porch.

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$2,061 total
includes taxes & fees
4 Oct - 5 Oct
Kildahl House - Boutique Farmhouse Suite #1
A bedroom with a brick wall, a bed, a desk, a TV, and a window.

5. 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 HK$1,514
HK$1,904 total
includes taxes & fees
30 Sept - 1 Oct
124 Lofts #3 - Downtown Dundee - Walk to Dining
A wicker tray with a pitcher and glasses on a wooden table on a porch.

6. Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful place to stay and the host was very welcoming and easy to work with!"
United States
Kevin B.
The price is HK$1,640
HK$2,061 total
includes taxes & fees
30 Sept - 1 Oct
Kildahl House - Boutique Farmhouse Suite #4
A bedroom with a brick wall, a bed, a desk, and a window with a view.

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$1,514
HK$1,904 total
includes taxes & fees
30 Sept - 1 Oct
124 Lofts #4 - Downtown Dundee - Walk to Dining
A wicker tray with a pitcher and glasses on a wooden table on a porch.

8. 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 HK$1,640
HK$2,003 total
includes taxes & fees
4 Oct - 5 Oct
Kildahl House - Boutique Farmhouse Suite #3
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

9. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (51 reviews)
"Incredible host and property."
United States
John V.
The price is HK$1,334
HK$1,912 total
includes taxes & fees
30 Sept - 1 Oct
Riverfront rental
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

10. ✨ 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 HK$998
HK$2,554 total
includes taxes & fees
6 Oct - 7 Oct
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A modern living room with a dining area, a sofa, a TV, and a fireplace.

11. 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 HK$1,765
HK$3,874 total
includes taxes & fees
26 Oct - 27 Oct
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

12. 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 HK$1,073
HK$1,678 total
includes taxes & fees
1 Oct - 2 Oct
Little Fox Cottage - A Cozy Riverview Getaway
A modern TopGolf facility with a prominent entrance, multiple levels, and a parking area.

13. Game Room & Fenced Yard Near O’Hare

Game Room & Fenced Yard Near O’Hare
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$1,507
HK$3,333 total
includes taxes & fees
30 Sept - 1 Oct
Game Room & Fenced Yard Near O’Hare
A sectional sofa with a glass coffee table in a sunroom with large windows.

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$5,492
HK$7,599 total
includes taxes & fees
5 Oct - 6 Oct
Modern Suburban Oasis- 14 guest House. Family Friendly!
A lakeside deck with chairs and a table, a wooden dock extending into the water, and a covered area in the background.

15. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
The price is HK$1,892
HK$4,552 total
includes taxes & fees
5 Oct - 6 Oct
Waterfront - Private Dock - Two Suites
A two-story house with a front porch, a stone exterior on the right side, and a green door.

16. 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$973
HK$1,946 total
includes taxes & fees
1 Oct - 2 Oct
The Main Event Game House on the Huntley Square!
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

17. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is HK$1,440
HK$3,979 total
includes taxes & fees
5 Oct - 6 Oct
King bed Crystal Lake Mchenry Cary Cozy
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

18. 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$1,227
HK$2,949 total
includes taxes & fees
27 Oct - 28 Oct
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
A modern living room with a sofa, a coffee table, and a view of the outdoors.

19. Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg
9.8 out of 10, Exceptional, (10 reviews)
"Super comfy for families and the nicest host. "
United States
Anonymous traveller
The price is HK$2,471
HK$4,406 total
includes taxes & fees
30 Sept - 1 Oct
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and a countertop.

20. 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
Geneva
9.6 out of 10, Exceptional, (27 reviews)
"The location is amazing! What a cute place. Just right for two people."
United States
Shara B.
The price is HK$983
HK$2,462 total
includes taxes & fees
30 Sept - 1 Oct
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
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

Quality Inn Schaumburg - Chicago near the Mall

Quality Inn Schaumburg - Chicago near the Mall

10/10 Excellent
"Excellent property. The front desk staff and housekeepers were very kind and accommodating. You really can’t beat the location either."
John 1-night trip
Posted 1 hour ago
Quality Inn Schaumburg - Chicago near the Mall

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
  • Use the map to find apartments and other holiday homes in the Sleepy Hollow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sleepy Hollow while they last

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 open concept home w/ game room + firepit: This holiday home rental outside of Sleepy Hollow offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and kitchenware, so that you can cook with friends or family. Make the most 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 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.