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Sleepy Hollow Vacation 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 vacation 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 AED 709
AED 899 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 AED 709
AED 899 total
includes taxes & fees
13 Aug - 14 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 AED 768
AED 977 total
includes taxes & fees
13 Aug - 14 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 AED 768
AED 977 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 AED 505
AED 1,326 total
includes taxes & fees
18 Aug - 19 Aug
✨ 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 AED 709
AED 899 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 AED 709
AED 899 total
includes taxes & fees
13 Aug - 14 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 AED 768
AED 977 total
includes taxes & fees
13 Aug - 14 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 AED 768
AED 977 total
includes taxes & fees
13 Aug - 14 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 AED 413
AED 699 total
includes taxes & fees
13 Aug - 14 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 AED 526
AED 1,305 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 AED 735
AED 1,070 total
includes taxes & fees
1 Sep - 2 Sep
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 AED 529
AED 1,172 total
includes taxes & fees
16 Aug - 17 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 AED 753
AED 1,300 total
includes taxes & fees
8 Sep - 9 Sep
The Main Event Game House on the Huntley Square!
House | 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 AED 660
AED 1,789 total
includes taxes & fees
23 Aug - 24 Aug
King bed Crystal Lake Mchenry Cary Cozy
Exterior

16. New Bath! Near Chicago and O’Hare +Fenced yard + Game room!

New Bath! 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 AED 767
AED 1,657 total
includes taxes & fees
16 Aug - 17 Aug
New Bath! Near Chicago and O’Hare +Fenced yard + Game room!
Paper towels, dining table

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 AED 767
AED 1,634 total
includes taxes & fees
1 Sep - 2 Sep
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, (18 reviews)
"Great place! "
United States
Isabella T.
The price is AED 496
AED 943 total
includes taxes & fees
17 Aug - 18 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 AED 460
AED 1,161 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 555
AED 1,043 total
includes taxes & fees
17 Aug - 18 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

Eaglewood Resort and Spa

Eaglewood Resort and Spa

10/10 Excellent
"It was a pleasure"
Elizabeth 1-night trip
Posted 1 hour ago
Eaglewood Resort and Spa

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?

Breathtaking home close to Schaumburg, Chicago: This vacation home rental outside of Sleepy Hollow offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a garden, and a selection of games so you can immerse yourself in your vacation.

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.