Sleepy Hollow Vacation Rentals from ￥15,440: 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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Vacation Rentals in Sleepy Hollow

"Fit our whole family nicely."

"Easy access to all St Charles "

"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"

￥44,718 total

includes taxes & fees

Sep 29 - Sep 30

"Great house, great neighborhood, host was amazing!"

"The house was very clean and spacious. A lot of activities to do "

￥227,076 total

includes taxes & fees

Sep 7 - Sep 8

"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...

￥31,360 total

includes taxes & fees

Sep 13 - Sep 14

"Only complaint was the fact that the yard was not cut and the grass needed to maintained"

￥67,812 total

includes taxes & fees

Sep 9 - Sep 10

"Very nice place and host is great "

￥52,078 total

includes taxes & fees

Sep 26 - Sep 27

"The property was very clean and comfortable!"

"Great property for a family get together. Very spacious and well equipped. Kristin was excellent!"

"Thank you for a great stay and accommodating our group!"

3 bedrooms, desk, iron/ironing board, travel crib

"A wonderful stay!! Good location. Very clean. Well stocked with everything we needed to enjoy ourselves! So many little touches made it a really nice place to stay. Comfortable and charming! "

￥41,458 total

includes taxes & fees

Sep 9 - Sep 10

"It is a small house but it has everything you need to be comfortable and the host is very friendly."

￥36,559 total

includes taxes & fees

Sep 15 - Sep 16

"Great Location and spacious with four bedrooms. Worked well with three adult children."

￥100,616 total

includes taxes & fees

Sep 7 - Sep 8

"A relaxing well appointed home with easy walking distance to downtown Woodstock!"

￥42,834 total

includes taxes & fees

Sep 16 - Sep 17

"This is a great property for a large family. There is plenty of space inside and out! A pond with a ton of bluegill kept us busy during the day, and s'mores were enjoyed around the fire pit(s) at night. This is a beautiful area of IL and we can't wait to come back! Communication with the host was clear and timely. All around great property and time!"

￥159,727 total

includes taxes & fees

Sep 9 - Sep 10

"We thoroughly enjoyed our stay at St. Geneva. Host was friendly and accommodating. Everything was clean and neat. Grounds and views were beautiful. Hope to stay there again when visiting family."

"The place was just like it was described and it’s pictures. Clean, cozy, and in a nice quiet area. Would stay again! "

￥40,907 total

includes taxes & fees

Sep 10 - Sep 11

￥161,743 total

includes taxes & fees

Sep 28 - Sep 29

"Nice quaint apartment. Easy access to the downtown area very close to Parks very walkable."

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Top Sleepy Hollow Hotel Reviews

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?

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.

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Sleepy Hollow Vacation Rentals

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Vacation Rentals in Sleepy Hollow

Breathtaking home close to Schaumburg, Chicago

Minutes to Downtown Saint Charles, Cozy/Chic Home

✽ Charming Cottage ✽ close to College/Town/Station

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

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

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

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

Spacious Ranch blocks away from downtown McHenry

Chicago-burb -Medinah -1 King and 1 Queen beds

Fox River/Chain of Lakes Waterfront Home with Hot Tub

Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,

- Beautiful Condo - King Bed - Free Waffle Breakfast -

Riverfront rental

Spacious 4BR Home with Game Room - LCP Collection

The Tailor House

Spacious A-Frame sleeps 25 on 5 wooded acres with a private fishing pond

"St Geneva" Private With River View! 10 min to Lamplight Equestrian Center

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Modern Suburban Oasis- 14 guest House. Family Friendly!

Charming Historic 2BR/1BA in DOWNTOWN EAST DUNDEE

Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

Explore a world of travel with Expedia

Frequently asked questions