Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

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

10.0 out of 10, Exceptional, (25)
"Great house, great neighborhood, host was amazing!"
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

Spacious Ranch blocks away from downtown McHenry

9.8 out of 10, Exceptional, (15)
"Very nice place and host is great "
The price is AU$506
includes taxes & fees
8 Oct - 9 Oct
Spacious Ranch blocks away from downtown McHenry

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

9.2 out of 10, Wonderful, (41)
"Very comfortable… enjoyed the property to the upmost.."
The price is AU$2,009
includes taxes & fees
6 Oct - 7 Oct
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

St. Charles Riverview Retreat

10.0 out of 10, Exceptional, (26)
"Very comfortable house and near downtown St Charles. We were only there 2 nights attending a family function. "
St. Charles Riverview Retreat

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

10.0 out of 10, Exceptional, (82)
"This home was very clean and comfortable. Lots of extras provided in the kitchen and bathroom. Such a nice location right on the river. And the host was very communicative which was very helpful. Would definitely stay here again!"
"St Geneva" Private With River View! 7 min to the Q Center

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

9.4 out of 10, Exceptional, (30)
"The property was very clean and comfortable!"
Chicago-burb -Medinah -1 King and 1 Queen beds

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (51)
"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!"
The price is AU$470
includes taxes & fees
13 Oct - 14 Oct
✽ Charming Cottage ✽ close to College/Town/Station

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

9.4 out of 10, Exceptional, (29)
"Our stay was great. Had an issue with the breaker but was able to get a hold of the host and fix the issue with no problems. "
The price is AU$429
includes taxes & fees
5 Oct - 6 Oct
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Paradise 4BR w/ Pool & Games

10.0 out of 10, Exceptional, (2)
"Everything was very clean, the location was good. My family and I enjoyed it a lot. Check-in was very easy and everything in the house was very up-to-date."
Paradise 4BR w/ Pool & Games

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

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 "
The price is AU$754
includes taxes & fees
2 Oct - 3 Oct
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

Cozy 3 bedroom river cottage w/ indoor fireplace

9.8 out of 10, Exceptional, (22)
"This was our second time here and was great as the first time. Its the prefect location for our event at Canlan Sports. We've already booked for next year even!Thanks!"
Cozy 3 bedroom river cottage w/ indoor fireplace

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (172)
"A truly memorable stay. I booked this home for a bridal party I was in and the home was perfect for all of us to connect together and relax in between wedding events. One of the best Vrbos I’ve stayed. Would love to come back "
Historic home with easy access to Chicago

Newly Remodeled 2BR 2BA Home ★ Close to Barrington

10.0 out of 10, Exceptional, (31)
"Convenient to Barrington. Easy to travel between locations for our events over the weekend."
Newly Remodeled 2BR 2BA Home ★ Close to Barrington

Pet Friendly, Near O’Hare, Fenced in, Cheerful Frida & Diego Home, up to 6 ppl

9.8 out of 10, Exceptional, (9)
"Beautiful place and loved the artwork and the history behind the art. Close to major highway and quite charming house. Will stay again next time in Chicago land area, "
The price is AU$666
includes taxes & fees
3 Oct - 4 Oct
Pet Friendly, Near O’Hare, Fenced in, Cheerful Frida & Diego Home, up to 6 ppl

Riverfront rental

9.8 out of 10, Exceptional, (32)
"Cute little place. Plenty of beds. Very comfy."
The price is AU$384
includes taxes & fees
5 Oct - 6 Oct
Riverfront rental

Minutes to Downtown Saint Charles, Cozy/Chic Home

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

The Tailor House

10.0 out of 10, Exceptional, (44)
"As advertized. Cozy and clean. Good food near by."
The price is AU$442
includes taxes & fees
14 Oct - 15 Oct
The Tailor House

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

9.8 out of 10, Exceptional, (6)
"The place was just like it was described and it’s pictures. Clean, cozy, and in a nice quiet area. Would stay again! "
The price is AU$411
includes taxes & fees
21 Oct - 22 Oct
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (13)
"Location was close to airport, restaurants and shopping"
The price is AU$387
includes taxes & fees
5 Oct - 6 Oct
Just remodeled apartment close to airport and mall

Charming 4-bedroom house in Lake Zurich w/ indoor fireplace and private backyard

9.6 out of 10, Exceptional, (4)
"Spacious house in a great neighborhood. Conveniently situated "
Charming 4-bedroom house in Lake Zurich w/ indoor fireplace and private 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

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sleepy Hollow holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sleepy Hollow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sleepy Hollow holiday rentals we have selected for you start as low as AU$384 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow holiday 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 holiday.

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 holiday rentals in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. Sleepy Hollow is known for its bars.

What are some of the best holiday rentals that Sleepy Hollow has to offer?

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.: This holiday home rental outside of Sleepy Hollow offers a patio, a garden and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 wider area, you’ll find Randall Oaks Golf Club and Hemmens Cultural Center.

What’s a holiday rental in Sleepy Hollow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sleepy Hollow. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.