Sleepy Hollow Vacation Rentals

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Vacation Rentals in Sleepy Hollow

- Beautiful Condo - King Bed - Free Waffle Breakfast -

Geneva
10.0 out of 10, Exceptional, (20)
"Beautiful place! Every detail was thought of for their guest!"
United States
Libby M.
$235 nightly
The price is $249
Dec 2 - Dec 3
Total with taxes and fees
- Beautiful Condo - King Bed - Free Waffle Breakfast -

Spacious open concept home w/ game room + firepit

Winfield
9.8 out of 10, Exceptional, (76)
"This was an excellent place to stay! "
United States
Marie
Spacious open concept home w/ game room + firepit

Cozy 3 bedroom river cottage w/ indoor fireplace

Barrington
9.8 out of 10, Exceptional, (23)
"Really cute little house just steps from the river. We would stay there again. "
United States
Jill F.
Cozy 3 bedroom river cottage w/ indoor fireplace

Breathtaking home close to Schaumburg, Chicago

Palatine
9.8 out of 10, Exceptional, (77)
"Great comfortable spot near the city"
United States
Jacob M.
Breathtaking home close to Schaumburg, Chicago

Sunny 1BR Apartment in the Surburbs

Arlington Heights
5.4 out of 10, (3)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
$145 nightly
The price is $156
Dec 2 - Dec 3
Total with taxes and fees
Sunny 1BR Apartment in the Surburbs

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

McHenry
9.2 out of 10, Wonderful, (41)
"The property management team, maintenance and cleaning staff are excellent. Communication was thorough and response time was quick. We enjoyed the pool very much."
United States
Allison K.
$1,088 nightly
The price is $1,153
Dec 2 - Dec 3
Total with taxes and fees
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Minutes to Downtown Saint Charles, Cozy/Chic Home

St. Charles
9.6 out of 10, Exceptional, (12)
"We had a very nice stay at this property. Farrah was easy to work with on entrance into the property, etc. "
United States
Ed S.
Minutes to Downtown Saint Charles, Cozy/Chic Home

"St Geneva" Private With River View! 7 min to the Q Center

St. Charles
10.0 out of 10, Exceptional, (86)
"The property was wonderful. It was so clean. Michael was a great host. He was a great communicator. I would stay there again when we go back to Illinois!"
United States
Shannon H.
"St Geneva" Private With River View! 7 min to the Q Center

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

Glen Ellyn
10.0 out of 10, Exceptional, (31)
"Great house, great neighborhood, host was amazing!"
United States
John B.
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

Just remodeled apartment close to airport and mall

Elk Grove Village
10.0 out of 10, Exceptional, (15)
"Location was close to airport, restaurants and shopping"
United States
Dorothy J.
$237 nightly
The price is $254
Dec 2 - Dec 3
Total with taxes and fees
Just remodeled apartment close to airport and mall

The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage

Arlington Heights
10.0 out of 10, Exceptional, (1)
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage

Charming 4 Bedroom home in the heart of Elgin

Elgin
9.4 out of 10, Exceptional, (38)
"Very clean, great space, will definitely stay again when in Elgin! "
United States
Jenifer V.
Charming 4 Bedroom home in the heart of Elgin

Spacious Ranch blocks away from downtown McHenry

McHenry
9.6 out of 10, Exceptional, (19)
"Great home and perfect location. "
United States
Steve B.
$309 nightly
The price is $327
Dec 2 - Dec 3
Total with taxes and fees
Spacious Ranch blocks away from downtown McHenry

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

Arlington Heights
9.0 out of 10, Wonderful, (4)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
United States
James b.
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

2.0 star property
Schaumburg
10.0 out of 10, Exceptional, (3)
"Super comfy for families and the nicest host. "
United States
Anonymous traveler
$485 nightly
The price is $519
Dec 2 - Dec 3
Total with taxes and fees
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Geneva
9.4 out of 10, Exceptional, (23)
"Great location for walking downtown and on 3rd street. Quiet, clean and nice touches. "
United States
Richard K.
$265 nightly
The price is $281
Dec 2 - Dec 3
Total with taxes and fees
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Modern Suburban Oasis- 14 guest House. Family Friendly!

Elgin
10.0 out of 10, Exceptional, (1)
$1,015 nightly
The price is $1,076
Dec 2 - Dec 3
Total with taxes and fees
Modern Suburban Oasis- 14 guest House. Family Friendly!

Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago

Schaumburg
10.0 out of 10, Exceptional, (12)
"This was a great place to hang out with friends and our family. A nice selection of sleeping space, a big table to eat or play games together inside, and a well equipped kitchen.We especially enjoyed the backyard- pictures and descriptions are accurate. With the pool, grill, and multiple seating options, it was a great place to have some fun and hang out and visit. We highly recommend staying here!"
United States
Brenda R.
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago

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

Barrington
9.6 out of 10, Exceptional, (5)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
United States
Sarah S.
$121 nightly
The price is $130
Dec 2 - Dec 3
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Schaumburg
9.8 out of 10, Exceptional, (32)
"Perfect for a family of 4. Had everything we needed."
United States
Rob K.
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
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 $130 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?

Spacious open concept home w/ game room + firepit: This vacation home rental outside of Sleepy Hollow offers a patio, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a microwave, and kitchenware, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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.