Sleepy Hollow Vacation Rentals

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Vacation Rentals in Sleepy Hollow

WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (190)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is CA $123
CA $131 total
includes taxes & fees
Jun 18 - Jun 19
WoodSpring Suites Chicago Addison
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (11)
"Pleasant stay."
The price is CA $235
CA $297 total
includes taxes & fees
Jun 17 - Jun 18
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.8 out of 10, Exceptional, (25)
"Such a great house and the owner was very responsive. Thank you!"
The price is CA $1,541
CA $2,914 total
includes taxes & fees
Jun 17 - Jun 18
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
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Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (15)
"Highly recommend this house! I would 100% stay here again when we are back in the area. The kids loved the activities and watching TV in the basement."
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Riverfront rental with fun activities
10.0 out of 10, Exceptional, (18)
"Cozy with lots of beds. A great pick for patio gathering and fun at the river. place was clean and had lots of little amenities on site."
The price is CA $295
CA $409 total
includes taxes & fees
Jun 25 - Jun 26
Riverfront rental with fun activities
Glen Ellyn Country Side Home
9.4 out of 10, Exceptional, (9)
"This place was great. So much space, it was clean and super quiet area. It was close to everything we needed and our host responded within minutes of request. If you have kids tons of space with pool. We travel year round coast to coast for lacrosse tournaments using vrbo. This house by far one of the best. We will be back!"
Glen Ellyn Country Side Home
Modern Open Concept Home with Pool Table by Train Station
8.8 out of 10, Excellent, (13)
"The home was very comfortable - it was modern and the beds were good. Unfortunately the repairs to make it rentable were not high quality. The bathroom sink in the half bath was leaking when we arrived. The door frame of the basement bathroom had fallen off & was lying on the floor when we arrived. The shower door in the upstairs bathroom would not stay on the track. However , none of these problems would deter me from renting again. They were just inconveniences."
Modern Open Concept Home with Pool Table by Train Station
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
8.0 out of 10, Very good, (2)
"We enjoyed our stay with plenty of space for two couples. Separate bedrooms/baths were perfect. Furnature in the living room needs updating."
The price is CA $258
CA $325 total
includes taxes & fees
Jun 17 - Jun 18
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
Fox Valley Farmhouse Overlooking The Fox River!
10.0 out of 10, Exceptional, (24)
"We were in town for a family wedding the same weekend as a dance/cheer competition. Since it was a small wedding, no hotel blocks had been set aside, and by the time I got around to booking, they were either full or super expensive. Then I found this place, and it was better than a hotel! We had three couples, so the three bedrooms and three bathrooms were ideal. The house was immaculate and well stocked with everything we needed. Every surface is new, and we loved the open kitchen and living...
Fox Valley Farmhouse Overlooking The Fox River!
Historic home with easy access to Chicago
9.6 out of 10, Exceptional, (154)
"Very nice and unique place. Great place to stay, but not for gatherings of more than 15. Enjoyed the quiet."
Historic home with easy access to Chicago
Spacious open concept home w/ game room + firepit
9.8 out of 10, Exceptional, (39)
"We were in town to host a wedding rehearsal dinner. We had various family members staying and had to do a lot of food prep for the dinner. The kitchen and dining area layout was terrific and the bedrooms fit the needs of everyone from kids, singles, and married couples. Since the house is supposed to accommodate 12 people, the living room area could use additional seating. We alerted the owner of some cleaning issues and she responded immediately."
Spacious open concept home w/ game room + firepit
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12
9.8 out of 10, Exceptional, (9)
"We stayed at this property for 6 nights to celebrate the Thanksgiving holiday with my family. The property was clean, well maintained, and had every cooking equipment that we needed. We had a terrific time."
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (31)
"Great house thank you"
The price is CA $234
CA $401 total
includes taxes & fees
Jun 25 - Jun 26
✽ Charming Cottage ✽ close to College/Town/Station
House with great location!
10.0 out of 10, Exceptional, (13)
"Alyssa is just amazing. Cannot say enough about how great she is. Super accommodating and understanding. When something isn’t right, she will fix it!"
The price is CA $233
CA $359 total
includes taxes & fees
Jul 8 - Jul 9
House with great location!
Log Cabin with HGTV Style Backyard INCREDIBLE property
8.2 out of 10, Very good, (16)
"Perfect amount of space for adults wanting to hang out, but not be on top of each other. Very relaxing. Would go back!"
Log Cabin with HGTV Style Backyard INCREDIBLE property
St. Charles Riverview Retreat
10.0 out of 10, Exceptional, (8)
"Close to a nice walking trail by the Fox river. Stairs are a bit steep, but one bedroom is on the main floor."
The price is CA $342
CA $627 total
includes taxes & fees
Jul 1 - Jul 2
St. Charles Riverview Retreat
Fox River Retreat
9.8 out of 10, Exceptional, (7)
"Just what we needed for a wedding we had during the weekend. Beautiful property right on the river! Thank you so much for hosting!"
Fox River Retreat
Comforting Retreat Near Woodfield Mall by RedAwning
10.0 out of 10, Exceptional, (5)
"Clean, nice place"
Comforting Retreat Near Woodfield Mall by RedAwning
Roomy, cozy Diamond Lakefront Home. Big Enough friends/family to be comfortable.
Roomy, cozy Diamond Lakefront Home. Big Enough friends/family to be comfortable.
Pet-Friendly Bartlett Farmhouse w/ Deck!
9.4 out of 10, Exceptional, (3)
"Well equipped. Lots of amenities, farmhouse ambience, comfortable beds. Good location."
Pet-Friendly Bartlett Farmhouse w/ Deck!
Don't see what you're looking for?
See all available properties in Sleepy Hollow
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.

Sleepy Hollow Vacation Rental Travel Info

Other types of properties in Sleepy Hollow you may be interested in

Wyndham Garden Schaumburg Chicago Northwest
3.0 star property
7.0 out of 10, Good, (1003)
"A good budget friendly place to stay if you are trying to save a buck while attending a convention. It's a nice 10ish min walk from the back of the hotel on a pathway, around a beautiful pond, and up a small grassy knoll to parking lot."
The price is CA $115
CA $133 total
includes taxes & fees
Jun 20 - Jun 21
Wyndham Garden Schaumburg Chicago Northwest
Motel 6 Rolling Meadows, IL - Chicago Northwest
2.0 star property
6.6 out of 10, (1004)
"pool covered with tarp, not in working condition for years. lobby with bullet proof glass over reception area desk & over 20 security camera images give initial perception of unsafe area but had no problems"
The price is CA $79
CA $91 total
includes taxes & fees
Jun 26 - Jun 27
Motel 6 Rolling Meadows, IL - Chicago Northwest
Eaglewood Resort and Spa
4.0 star property
8.4 out of 10, Very good, (1003)
"My Fiancé and I only stayed for the weekend. Staff was rude and needs to get it together, other than that and me not caring like a Karen, beautiful stay! Room was clean, but conditioner wasn’t filled & you could tell by the dust it wasn’t freshly cleaned (soap dish & lamps) tub was just stained no biggie. Pool and spa close early and are in a different building just for the ones wondering (had to search for a min) & be prepared to yawn at the mildly snobby people loll! Other than that k1 racing...
The price is CA $163
CA $209 total
includes taxes & fees
Jul 8 - Jul 9
Eaglewood Resort and Spa
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sleepy Hollow. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: This vacation home rental outside of Sleepy Hollow is located in the city center and offers a barbecue grill, air-conditioning, and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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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