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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 #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$1,514
HK$1,921 total
includes taxes & fees
16 Aug - 17 Aug
124 Lofts #1 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

2. 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$1,514
HK$1,921 total
includes taxes & fees
17 Aug - 18 Aug
124 Lofts #3 - Downtown Dundee - Walk to Dining
Property grounds

3. 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
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
Coffee/tea maker, fridge, microwave, oven

5. ✨ 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$1,124
HK$2,887 total
includes taxes & fees
8 Sept - 9 Sept
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
1 bedroom, desk, iron/ironing board, WiFi

6. 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$1,921 total
includes taxes & fees
17 Aug - 18 Aug
124 Lofts #4 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

7. 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$1,514
HK$1,921 total
includes taxes & fees
17 Aug - 18 Aug
124 Lofts #2 - Downtown Dundee - Walk to Dining
Property grounds

8. 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$2,078 total
includes taxes & fees
16 Aug - 17 Aug
Kildahl House - Boutique Farmhouse Suite #2
Property grounds

9. 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
Outdoor dining

10. 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$1,130
HK$1,796 total
includes taxes & fees
18 Aug - 19 Aug
Little Fox Cottage - A Cozy Riverview Getaway
Outdoor dining

11. 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
Interior

12. 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$1,569
HK$2,287 total
includes taxes & fees
1 Sept - 2 Sept
Riverfront rental
Terrace/patio

13. - 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$1,236
HK$2,632 total
includes taxes & fees
20 Aug - 21 Aug
- Fully-Equipped Condo - King Bed - Massive yard -
Exterior

14. 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!
2 bedrooms

15. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is HK$1,281
HK$3,687 total
includes taxes & fees
17 Aug - 18 Aug
King bed Crystal Lake Mchenry Cary Cozy
Exterior

16. 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$1,688
HK$3,602 total
includes taxes & fees
16 Aug - 17 Aug
Near Chicago and O’Hare +Fenced yard + Game room!
Paper towels, dining tables

17. 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
Paper towels

18. Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (19 reviews)
"Great place! "
United States
Isabella T.
The price is HK$1,059
HK$2,015 total
includes taxes & fees
16 Aug - 17 Aug
Just remodeled apartment close to airport and mall
Smart TV

19. 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
9.4 out of 10, Exceptional, (26 reviews)
"Great location! Everything was exactly as shown on the website. Cita, as always, communicated quickly when I had any questions. I enjoyed a peaceful, quiet stay."
United States
Karen M.
The price is HK$1,002
HK$2,500 total
includes taxes & fees
10 Sept - 11 Sept
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Exterior

20. 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$1,318
HK$2,387 total
includes taxes & fees
26 Aug - 27 Aug
The Tailor House
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

8/10 Good
"It was a nice stay. Quiet. Close to everything. Nice bkft."
MaryAnn 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
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  • 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?

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.