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Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Sleepy Hollow vacation rentals

1 bedroom, desk, iron/ironing board, WiFi

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 ￥31,619
￥39,755 total
includes taxes & fees
Jul 28 - Jul 29
124 Lofts #1 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (26 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 ￥31,619
￥39,755 total
includes taxes & fees
Jul 28 - Jul 29
124 Lofts #3 - Downtown Dundee - Walk to Dining
Property grounds

Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
The price is ￥34,240
￥43,036 total
includes taxes & fees
Jul 30 - Jul 31
Kildahl House - Boutique Farmhouse Suite #2
Property grounds

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 ￥34,240
￥43,036 total
includes taxes & fees
Aug 2 - Aug 3
Kildahl House - Boutique Farmhouse Suite #1
Coffee/tea maker, fridge, microwave, oven

✨ 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 ￥23,854
￥57,359 total
includes taxes & fees
Aug 10 - Aug 11
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
1 bedroom, desk, iron/ironing board, WiFi

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 ￥31,619
￥39,755 total
includes taxes & fees
Jul 28 - Jul 29
124 Lofts #4 - Downtown Dundee - Walk to Dining
1 bedroom, desk, iron/ironing board, WiFi

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)
"Great spot in the heart of the village walking to everything, incredible hospitality with every detail covered."
United States
Robin R.
The price is ￥31,619
￥39,234 total
includes taxes & fees
Jul 28 - Jul 29
124 Lofts #2 - Downtown Dundee - Walk to Dining
Property grounds

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 ￥34,240
￥43,036 total
includes taxes & fees
Aug 2 - Aug 3
Kildahl House - Boutique Farmhouse Suite #4
Property grounds

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 ￥34,240
￥43,036 total
includes taxes & fees
Aug 2 - Aug 3
Kildahl House - Boutique Farmhouse Suite #3
Interior

Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (45 reviews)
"Cozy home, perfect for a relaxting time away "
United States
Phoenicia
The price is ￥30,964
￥45,316 total
includes taxes & fees
Jul 28 - Jul 29
Riverfront rental
Exterior

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 ￥31,813
￥70,839 total
includes taxes & fees
Jul 28 - Jul 29
New Bath! Near Chicago and O’Hare +Fenced yard + Game room!
Outdoor dining

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 ￥23,454
￥57,845 total
includes taxes & fees
Aug 10 - Aug 11
Spacious 3 Bedroom
Paper towels

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 ￥22,117
￥41,537 total
includes taxes & fees
Aug 7 - Aug 8
Just remodeled apartment close to airport and mall
Paper towels, dining table

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 ￥36,985
￥75,321 total
includes taxes & fees
Aug 9 - Aug 10
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Exterior

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (69 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is ￥29,489
￥52,609 total
includes taxes & fees
Aug 7 - Aug 8
✽ Charming Cottage ✽ close to College/Town/Station
Smart TV

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 ￥20,536
￥51,769 total
includes taxes & fees
Jul 28 - Jul 29
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Smart TV, books

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Geneva
9.4 out of 10, Exceptional, (34 reviews)
"The host was very welcoming "
United States
Karen B.
The price is ￥24,378
￥58,718 total
includes taxes & fees
Jul 28 - Jul 29
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
House | 2 bedrooms

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is ￥43,069
￥95,129 total
includes taxes & fees
Jul 30 - Jul 31
King bed Crystal Lake Mchenry Cary Cozy
Smart TV, books

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, (9 reviews)
"Super comfy for families and the nicest host. "
United States
Anonymous traveler
The price is ￥47,183
￥97,448 total
includes taxes & fees
Jul 28 - Jul 29
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Property grounds

Perfect Family Getaway: Spacious 5BR Home in Barrington

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is ￥180,213
￥670,564 total
includes taxes & fees
Jul 28 - Jul 29
Perfect Family Getaway: Spacious 5BR Home in Barrington
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

Country Inn & Suites by Radisson, Elk Grove Village/Itasca

Country Inn & Suites by Radisson, Elk Grove Village/Itasca

10/10 Excellent
"Great place to stay! CLEAN and quiet!! Staff was phenomenal!"
Patricia 2-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Elk Grove Village/Itasca

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 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?

Riverfront rental: This vacation home rental outside of Sleepy Hollow is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.