Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Sleepy Hollow vacation rentals

Outdoor dining

Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
The price is ￥24,133
￥57,815 total
includes taxes & fees
Jun 8 - Jun 9
Spacious 3 Bedroom
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
9.8 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is ￥28,669
￥51,483 total
includes taxes & fees
Jun 2 - Jun 3
✽ Charming Cottage ✽ close to College/Town/Station
Smart TV

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is ￥15,975
￥28,166 total
includes taxes & fees
Jun 8 - Jun 9
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
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, (16 reviews)
"Great place! "
United States
Isabella T.
The price is ￥21,501
￥40,210 total
includes taxes & fees
Jun 3 - Jun 4
Just remodeled apartment close to airport and mall
Fridge, microwave, oven, stovetop

Recharge in This Charming 1BR Apt

Recharge in This Charming 1BR Apt
Arlington Heights
9.0 out of 10, Wonderful, (2 reviews)
"Nice for the price. Excellent location."
United States
Al E.
The price is ￥12,264
￥28,924 total
includes taxes & fees
Jun 8 - Jun 9
Recharge in This Charming 1BR Apt
Outdoor dining

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 ￥20,068
￥32,410 total
includes taxes & fees
Jun 2 - Jun 3
Little Fox Cottage - A Cozy Riverview Getaway
Exterior

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (51 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is ￥21,024
￥41,017 total
includes taxes & fees
Jun 7 - Jun 8
The Tailor House
Smart TV

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Geneva
9.6 out of 10, Exceptional, (9 reviews)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is ￥21,024
￥51,672 total
includes taxes & fees
Jun 2 - Jun 3
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Terrace/patio

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (39 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 ￥31,535
￥60,935 total
includes taxes & fees
Jun 5 - Jun 6
- Fully-Equipped Condo - King Bed - Massive yard -
Interior

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (40 reviews)
"Great place to stay near St. Charles/Geneva. Will definitely stay again next time we visit. Plenty of room, great view, super easy access to west suburbs, North Ave./Randal Rd,/25/31, but tucked away from the hustle and bustle etc. Host was great, respected our privacy. Super hot shower! "
United States
Elsa L.
The price is ￥30,261
￥41,526 total
includes taxes & fees
Jun 8 - Jun 9
Riverfront rental
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)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
United States
Jerilynn L.
The price is ￥17,034
￥46,569 total
includes taxes & fees
Jun 2 - Jun 3
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Terrace/patio

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (27 reviews)
"Lovely home. We had a group of seven adults. The home was super clean, thoughtfully designed for guest comfort and close to downtown. Would stay again!!"
United States
Julie C.
The price is ￥31,058
￥60,091 total
includes taxes & fees
Jun 16 - Jun 17
- Beautiful Condo - King Bed - Free Waffle Breakfast -
Interior

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.4 out of 10, Exceptional, (6 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is ￥28,847
￥92,182 total
includes taxes & fees
Jun 3 - Jun 4
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
House, Smoking | 2 bedrooms

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is ￥23,467
￥71,290 total
includes taxes & fees
Jun 10 - Jun 11
King bed Crystal Lake Mchenry Cary Cozy
Fridge, microwave, oven, stovetop

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Geneva
9.8 out of 10, Exceptional, (35 reviews)
"Great stay. Owner very easy to work with and place was clean. Would reccomend."
United States
Jason W.
The price is ￥21,215
￥51,715 total
includes taxes & fees
Jun 3 - Jun 4
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Shower, eco-friendly toiletries, hair dryer, towels

Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.4 out of 10, Very Good, (7 reviews)
"Cute and cozy little house. Convenient location. I would stay there again if the need ever comes up again. "
United States
holly g.
The price is ￥27,084
￥46,595 total
includes taxes & fees
Jun 2 - Jun 3
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
Property grounds

Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (14 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
The price is ￥33,287
￥41,669 total
includes taxes & fees
Jun 4 - Jun 5
Kildahl House - Boutique Farmhouse Suite #2
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, (22 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 ￥30,739
￥38,984 total
includes taxes & fees
Jun 2 - Jun 3
124 Lofts #3 - Downtown Dundee - Walk to Dining
Private kitchen

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is ￥27,393
￥70,386 total
includes taxes & fees
Jun 3 - Jun 4
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
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 Itasca

Hyatt Place Itasca

6/10 Okay
"I am sooo dissapointed in the Hyatt PLACES! I travel alot and have stayed at Hyatt places many times, but they are going downhill. I would consider them almost dirty. Not 100% dirty but 80% dirty. They need a deep cleaning. Just like the Itasca Hyatt Place. I'm staying someplace else next time...and get the elevator fixed. I was there 4 days, and nobody was even looking to fix it!"
Ellen 3-night trip
Posted 3 hours ago
Hyatt Place 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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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.