Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Sleepy Hollow vacation rentals

Fridge, microwave, oven, stovetop

Cozy & Serene 1BR Escape

Cozy & Serene 1BR Escape
Arlington Heights
7.6 out of 10, Good, (8 reviews)
"Comfortable stay; great communication"
United States
Alyssa
The price is ￥13,026
￥29,777 total
includes taxes & fees
Apr 27 - Apr 28
Cozy & Serene 1BR Escape
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, (8 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is ￥15,123
￥27,224 total
includes taxes & fees
Apr 17 - Apr 18
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
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)
"We really enjoyed our stay here. The kitchen had everything we needed and the house was very nice. Finding the driveway was a bit tricky in the dark. Thank you for a welcoming place to call home while we were in town for a wedding. "
United States
Cathy
The price is ￥16,441
￥42,508 total
includes taxes & fees
Apr 20 - Apr 21
- Fully-Equipped Condo - King Bed - Massive yard -
Fridge, microwave, oven, stovetop

Recharge in This Charming 1BR Apt

Recharge in This Charming 1BR Apt
Arlington Heights
8.0 out of 10, Very Good, (1 review)
"Cute and cozy. Easy access with parking"
United States
Jenna R.
The price is ￥13,979
￥31,233 total
includes taxes & fees
Apr 29 - Apr 30
Recharge in This Charming 1BR Apt
Terrace/patio

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (25 reviews)
"We had a lovely stay! The property was well appointed and comfortable. The host was very responsive. "
United States
Kathryn M.
The price is ￥14,297
￥39,899 total
includes taxes & fees
Apr 20 - Apr 21
- Beautiful Condo - King Bed - Free Waffle Breakfast -
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 ￥24,480
￥76,448 total
includes taxes & fees
Apr 20 - Apr 21
King bed Crystal Lake Mchenry Cary Cozy
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, (17 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is ￥20,015
￥32,156 total
includes taxes & fees
Apr 19 - Apr 20
Little Fox Cottage - A Cozy Riverview Getaway
Exterior

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (51 reviews)
"I really enjoyed the place "
United States
Ahmed A.
The price is ￥20,968
￥40,740 total
includes taxes & fees
Apr 20 - Apr 21
The Tailor House
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, (33 reviews)
"We had a great stay in Geneva for the night. Our spot was very convenient to lots of places around town. I would definitely recommend staying at this location! "
United States
jennifer f.
The price is ￥20,015
￥51,567 total
includes taxes & fees
May 4 - May 5
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Fridge, microwave, oven, stovetop

Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights
Arlington Heights
8.0 out of 10, Very Good, (1 review)
"Parking was a problem "
United States
Brian W.
The price is ￥13,026
￥29,777 total
includes taxes & fees
Apr 27 - Apr 28
Chic 1BR Apt -Arlington Heights
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, (24 reviews)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
United States
Jerilynn L.
The price is ￥21,739
￥51,717 total
includes taxes & fees
Apr 19 - Apr 20
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Exterior

The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
9.8 out of 10, Exceptional, (19 reviews)
"Our stay was wonderful and was exactly as described. Able to walk into town and the games were a lot of fun."
United States
Christine C.
The price is ￥20,174
￥41,245 total
includes taxes & fees
Apr 19 - Apr 20
The Main Event Game House on the Huntley Square!
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
9.6 out of 10, Exceptional, (4 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is ￥20,730
￥81,733 total
includes taxes & fees
Apr 22 - Apr 23
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
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 ￥20,968
￥50,862 total
includes taxes & fees
Apr 19 - Apr 20
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Interior

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (39 reviews)
"Luci was excellent. A quiet lovely house on the river. Thank you"
United States
Brian N.
The price is ￥22,239
￥31,961 total
includes taxes & fees
Apr 23 - Apr 24
Riverfront rental
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)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is ￥23,828
￥43,165 total
includes taxes & fees
May 1 - May 2
Just remodeled apartment close to airport and mall
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 ￥25,819
￥68,777 total
includes taxes & fees
Apr 20 - Apr 21
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (62 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is ￥27,003
￥48,818 total
includes taxes & fees
May 6 - May 7
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.4 out of 10, Very Good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is ￥27,799
￥80,008 total
includes taxes & fees
Apr 20 - Apr 21
4BR Near Woodfield Mall & Metra | LCP Collection
Interior

Basement Suite, Separate-entrance in Prime Location

Basement Suite, Separate-entrance in Prime Location
Schaumburg
6.8 out of 10, (6 reviews)
"The property was clean and what we needed for our trip. I would suggest adding some hand towels in the bathroom and dish towels or paper towels in the kitchen since it does provide an opportunity to cook. One bed was a little high for the vertically challenged! "
United States
Amy W.
The price is ￥31,770
￥41,975 total
includes taxes & fees
Apr 17 - Apr 18
Basement Suite, Separate-entrance in Prime Location
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

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

8/10 Good
"April 2026: Hotel is under renovation, not a major disruption to our stay, however just be aware. The hotel is definitely in need of a renovation as the rooms are getting dated. Our late night check-in went extremely well and the individual working the desk was very accommodating. Unfortunately, the breakfast buffet was expensive ($18.95/person), poorly maintained, poor quality and definitely not worth $18.95. Very disappointing. Overall, a good, quality hotel; however, the quality of level I would expect a Doubletree."
Mark 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

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?

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.