Sleepy Hollow Vacation Rentals

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Our top choices for Sleepy Hollow vacation rentals

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.
$160 nightly
The price is $171
May 17 - May 18
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

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.
$218 nightly
The price is $231
May 18 - May 19
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway

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.
$237 nightly
The price is $254
May 25 - May 26
Total with taxes and fees
Just remodeled apartment close to airport and mall

- 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
$275 nightly
The price is $291
May 19 - May 20
Total with taxes and fees
- Fully-Equipped Condo - King Bed - Massive yard -

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (27 reviews)
"We had a lovely stay! The property was well appointed and comfortable. The host was very responsive. "
United States
Kathryn M.
$265 nightly
The price is $281
May 19 - May 20
Total with taxes and fees
- Beautiful Condo - King Bed - Free Waffle Breakfast -

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (40 reviews)
"Luci was excellent. A quiet lovely house on the river. Thank you"
United States
Brian N.
$235 nightly
The price is $236
May 17 - May 18
Total with taxes and fees
Riverfront rental

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (67 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
$297 nightly
The price is $315
May 31 - Jun 1
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (51 reviews)
"I really enjoyed the place "
United States
Ahmed A.
$266 nightly
The price is $282
May 26 - May 27
Total with taxes and fees
The Tailor House

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
$451 nightly
The price is $483
May 18 - May 19
Total with taxes and fees
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

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.
$296 nightly
The price is $327
May 18 - May 19
Total with taxes and fees
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

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.
$176 nightly
The price is $192
May 18 - May 19
Total with taxes and fees
Chic 1BR Apt -Arlington Heights

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.
$323 nightly
The price is $357
May 20 - May 21
Total with taxes and fees
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (13 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
$236 nightly
The price is $263
May 26 - May 27
Total with taxes and fees
Kildahl House - Boutique Farmhouse Suite #2

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.
$570 nightly
The price is $606
May 18 - May 19
Total with taxes and fees
4BR Near Woodfield Mall & Metra | LCP Collection

124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (21 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.
$211 nightly
The price is $235
May 25 - May 26
Total with taxes and fees
124 Lofts #3 - Downtown Dundee - Walk to Dining

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.
$256 nightly
The price is $271
May 18 - May 19
Total with taxes and fees
The Main Event Game House on the Huntley Square!

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.
$290 nightly
The price is $320
May 17 - May 18
Total with taxes and fees
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
$341 nightly
The price is $361
May 20 - May 21
Total with taxes and fees
Spacious 3 Bedroom

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

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
$412 nightly
The price is $437
May 18 - May 19
Total with taxes and fees
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (14 reviews)
"Everything was as described, great location too! "
United States
Freddy M.
$235 nightly
The price is $262
May 21 - May 22
Total with taxes and fees
Kildahl House - Boutique Farmhouse Suite #1
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

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 $171 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 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.