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Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Sleepy Hollow vacation rentals

Interior

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, (13 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
$176 nightly
The price is $188
Jul 7 - Jul 8
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
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.
$277 nightly
The price is $279
Jul 13 - Jul 14
Total with taxes and fees
- Beautiful Condo - King Bed - Free Waffle Breakfast -
Paper towels, dining tables

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
wheaton
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
$493 nightly
The price is $523
Jul 7 - Jul 8
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Outdoor dining

Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
$334 nightly
The price is $354
Jul 7 - Jul 8
Total with taxes and fees
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, (17 reviews)
"Great place! "
United States
Isabella T.
$239 nightly
The price is $256
Jul 20 - Jul 21
Total with taxes and fees
Just remodeled apartment close to airport and mall
House | 2 bedrooms

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
$468 nightly
The price is $496
Jul 13 - Jul 14
Total with taxes and fees
King bed Crystal Lake Mchenry Cary Cozy
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 is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
$303 nightly
The price is $321
Jul 26 - Jul 27
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Terrace/patio

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (41 reviews)
"Great place, well appointed, worked well for our needs!! Host was very responsive to any questions/requests. "
United States
Amy C.
$286 nightly
The price is $288
Jul 7 - Jul 8
Total with taxes and fees
- Fully-Equipped Condo - King Bed - Massive yard -
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.
$192 nightly
The price is $203
Jul 7 - Jul 8
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
Exterior

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (52 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
$331 nightly
The price is $351
Jul 20 - Jul 21
Total with taxes and fees
The Tailor House
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.
$547 nightly
The price is $580
Jul 8 - Jul 9
Total with taxes and fees
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Interior

Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (44 reviews)
"Cozy home, perfect for a relaxting time away "
United States
Phoenicia
$299 nightly
The price is $317
Jul 19 - Jul 20
Total with taxes and fees
Riverfront rental
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, (25 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.
$218 nightly
The price is $243
Jul 7 - Jul 8
Total with taxes and fees
124 Lofts #3 - Downtown Dundee - Walk to Dining
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
$533 nightly
The price is $570
Jul 7 - Jul 8
Total with taxes and fees
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Property grounds

Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (16 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
$236 nightly
The price is $263
Jul 14 - Jul 15
Total with taxes and fees
Kildahl House - Boutique Farmhouse Suite #2
TV

Relaxing Lake Zurich 3BR + Patio | LCP Collection

Relaxing Lake Zurich 3BR + Patio | LCP Collection
Lake Zurich
8.8 out of 10, Excellent, (6 reviews)
"This was by far the cleanest VRBO we have rented. The location was perfect for our visit. The fully fenced yard was great for our dogs. The host promptly responded to questions I had prior to and during our stay. "
United States
diana w.
$468 nightly
The price is $496
Jul 7 - Jul 8
Total with taxes and fees
Relaxing Lake Zurich 3BR + Patio | LCP Collection
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
$425 nightly
The price is $450
Jul 7 - Jul 8
Total with taxes and fees
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
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)
"Great location for shopping! Very cute apartment. Easy check in and checkout. "
United States
JONICA R.
$317 nightly
The price is $350
Aug 3 - Aug 4
Total with taxes and fees
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Interior

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, (8 reviews)
"Cute and cozy little house. Convenient location. I would stay there again if the need ever comes up again. "
United States
holly g.
$288 nightly
The price is $305
Jul 7 - Jul 8
Total with taxes and fees
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
Exterior

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

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
$442 nightly
The price is $473
Jul 7 - Jul 8
Total with taxes and fees
Game room+ New Bath! Near Chicago and O’Hare +Fenced yard
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

Marriott Chicago Schaumburg

Marriott Chicago Schaumburg

10/10 Excellent
"Good. Clean. Easy to checkin. Starbucks in the lobby. Enough parking."
Hemal 1-night trip
Posted 3 hours ago
Marriott Chicago Schaumburg

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Randall Oaks Golf Club and Hemmens Cultural Center.

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.