Sleepy Hollow Vacation Rentals from $263: Search Short-Term Rentals

Q: 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.

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Our top choices for Sleepy Hollow vacation rentals

1. 124 Lofts #1 - Downtown Dundee - Walk to Dining

West Dundee

Haggard A.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

2. 124 Lofts #3 - Downtown Dundee - Walk to Dining

West Dundee

David K.

$208 nightly

Aug 26 - Aug 27

Total with taxes and fees

3. Kildahl House - Boutique Farmhouse Suite #1

West Dundee

Thea

$221 nightly

Sep 23 - Sep 24

Total with taxes and fees

4. Kildahl House - Boutique Farmhouse Suite #4

West Dundee

Robert W.

$239 nightly

Aug 30 - Aug 31

Total with taxes and fees

5. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

Elgin

Phuong N.

$336 nightly

Aug 31 - Sep 1

Total with taxes and fees

6. 124 Lofts #4 - Downtown Dundee - Walk to Dining

West Dundee

Shannon

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

7. 124 Lofts #2 - Downtown Dundee - Walk to Dining

West Dundee

Zachary K.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

8. Kildahl House - Boutique Farmhouse Suite #2

West Dundee

Jen C.

$239 nightly

Aug 30 - Aug 31

Total with taxes and fees

9. Kildahl House - Boutique Farmhouse Suite #3

West Dundee

Jennifer W.

$239 nightly

Aug 30 - Aug 31

Total with taxes and fees

10. Little Fox Cottage - A Cozy Riverview Getaway

Fox River Grove

Jeff P.

$206 nightly

Aug 31 - Sep 1

Total with taxes and fees

11. Riverfront rental

South Elgin

Phoenicia

$248 nightly

Sep 1 - Sep 2

Total with taxes and fees

12. The Main Event Game House on the Huntley Square!

Huntley

BENJAMIN B.

$260 nightly

Sep 1 - Sep 2

Total with taxes and fees

13. Spacious 3 Bedroom

Cary

Kim B.

$335 nightly

Aug 25 - Aug 26

Total with taxes and fees

14. King bed Crystal Lake Mchenry Cary Cozy

Cary

$446 nightly

Aug 27 - Aug 28

Total with taxes and fees

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

Geneva

Shara B.

$286 nightly

Aug 25 - Aug 26

Total with taxes and fees

16. Chicago&O’Hare+King Bed+WiFi+Deck&Fence

Schaumburg

Central A.

$415 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Geneva

Amy C.

$270 nightly

Aug 26 - Aug 27

Total with taxes and fees

18. - Beautiful Condo - King Bed - Free Waffle Breakfast -

Geneva

Nikki G.

$286 nightly

Aug 26 - Aug 27

Total with taxes and fees

19. The Tailor House

Woodstock

Brittany H.

$268 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Carol Stream

Jay S.

$510 nightly

Aug 26 - Aug 27

Total with taxes and fees

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Top Sleepy Hollow Hotel Reviews

The Westin Chicago Northwest

8/10 Good

"This is a great location near the airport and close to a Metra station. The staff here are very friendly and were great with instructions and communication. One thing to note is that they do host events and while we stayed there were two weddings going on which made it a little challenging to sleep with guests and hotel patrons returning to their rooms at early hours. The hotel does not have traditional hallways either so you can see the rooms as soon as you step off the elevator which can also get noisy as people are getting off. This was our experience as we were given a room right next to the elevator so unsure about the noise levels farther away from the elevators but something to keep in mind if you’re trying to get some sleep. Regardless, we would definitely stay here again and found this hotel to be perfect for our trip."

Eaglewood Resort and Spa

8/10 Good

"Stayed here for the nostalgia. My dad worked for Nordic Hills when I was a kid and I spent a lot of time there in the 70’s and 80’s. It has been significantly changed but not for the better. The cool octagonal indoor pool is gone, the outdoor pool is gone. There is a new indoor pool, which is decent. The lady who runs the little bowling alley is very nice. They really need to fix the bowling alley if they’re going to charge guests to use it. $30 per hour is a little expensive for electronics that doesn’t count the pins correctly. There aren’t enough sizes to use bowling shoes and the balls and lanes are very worn. Overall we had a fun time though. They should just include it in the price if they’re room honestly. The downstairs restaurant used to be awesome. Now it’s meh. Very limited menu of seemingly microwaved food. Bring back The Viking Room and the two-sided fireplace! We were charged $10 per car to park in the parking lot. Not sure why…Glad we went but they should have kept the stuff that made the place cool and unique back in the day. People seem to like the golf course."

DoubleTree by Hilton Libertyville - Mundelein

8/10 Good

"Hotel was nice staff was nice , would've rate higher but wasn't made aware of parking lot paving and construction around the building prior to my stay , overall always have a great experience but this particular stay was hindered by the mess in the lot and noise in the morning during the day from them working on it ."

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 $263 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.

Room 1

Check prices for these dates

Our top choices for Sleepy Hollow vacation rentals

1. 124 Lofts #1 - Downtown Dundee - Walk to Dining

2. 124 Lofts #3 - Downtown Dundee - Walk to Dining

3. Kildahl House - Boutique Farmhouse Suite #1

4. Kildahl House - Boutique Farmhouse Suite #4

5. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

6. 124 Lofts #4 - Downtown Dundee - Walk to Dining

7. 124 Lofts #2 - Downtown Dundee - Walk to Dining

8. Kildahl House - Boutique Farmhouse Suite #2

9. Kildahl House - Boutique Farmhouse Suite #3

10. Little Fox Cottage - A Cozy Riverview Getaway

11. Riverfront rental

12. The Main Event Game House on the Huntley Square!

13. Spacious 3 Bedroom

14. King bed Crystal Lake Mchenry Cary Cozy

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

16. Chicago&O’Hare+King Bed+WiFi+Deck&Fence

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

18. - Beautiful Condo - King Bed - Free Waffle Breakfast -

19. The Tailor House

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

Find vacation rentals that suit your style

Top Sleepy Hollow Hotel Reviews

The Westin Chicago Northwest

DoubleTree by Hilton Chicago - Arlington Heights

Chez Hotel Arlington Heights

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn Chicago Schaumburg - O'Hare Airport

Eaglewood Resort and Spa

Hyatt Regency Schaumburg Chicago

Hyatt Place Itasca

DoubleTree by Hilton Libertyville - Mundelein

Find out more about Sleepy Hollow

Frequently asked questions