Search Holiday Rentals in Sleepy Hollow

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Top Holiday Rentals in Sleepy Hollow

The Tailor House
10.0 out of 10, Exceptional, (36)
"3 CA Family members joined the two of us from IL. We attended a June 15 family wedding at a nearby Woodstock Golf resort. The little home is charming and cozy and was perfect size for us to be comfortable. If there would be one thing I would suggest be added : Perhaps a couple of full length mirrors on the back of the bedroom doors so we ladies could have used those as we dressed for the wedding. Not earthshaking but I think it would be a nice addition. Thanks to the host owners for our...
The price is £237
includes taxes & fees
12 Nov - 13 Nov
The Tailor House
Chicago&O’Hare/King Bed/Fenced yard/Game room
10.0 out of 10, Exceptional, (21)
"We had 5 people stay. 3 bedrooms and the two couches that fold out into beds. We hung out on the deck each night, but never ended up using the fire pit. Was a warm night anyway. Great stay. "
The price is £344
includes taxes & fees
11 Nov - 12 Nov
Chicago&O’Hare/King Bed/Fenced yard/Game room
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.6 out of 10, Exceptional, (28)
"Huge property with amazing basement and pool. Comfortably slept 14 (almost everyone had their own bed) and close to great golf courses plus Kief’s Reef Bar and McHenry. Would highly recommend. "
The price is £1,096
includes taxes & fees
4 Nov - 5 Nov
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Chicago-burb -Medinah -1 King and 1 Queen beds
9.4 out of 10, Exceptional, (14)
"Everything was exactly as it was described. Super clean, easy to find, great neighborhood. "
Chicago-burb -Medinah -1 King and 1 Queen beds
Riverfront rental with fun activities
10.0 out of 10, Exceptional, (21)
"We enjoyed the home, the views of the river and the kind accommodations from Luci! She had all the things we needed and MORE! "
The price is £175
includes taxes & fees
3 Nov - 4 Nov
Riverfront rental with fun activities
Historic home with easy access to Chicago
9.6 out of 10, Exceptional, (159)
"Amazing home. More stunning than pictures. Lots of places to gather as a group or have solitude. Beds very comfortable. Kitchen well equipped. Neighborhood quiet and walkable. Enjoyed outdoor dining on deck, quiet porch swing mornings, happy hour toasting in the sunroom, playing the grand piano, and cozing up in the living room for a movie. 5 adult family members gathering for graduation from a graduate program at Midwestern University.. Highly recommend!"
Historic home with easy access to Chicago
Spacious open concept home w/ game room + firepit
9.8 out of 10, Exceptional, (47)
"Our family of 4 had a wonderful stay here! Great neighborhood and a spacious home! The beds were super comfy & the home was decorated nicely! Thank you for having us Amanda! We’ll be back :) "
Spacious open concept home w/ game room + firepit
Pet-Friendly Bartlett Farmhouse w/ Deck!
9.6 out of 10, Exceptional, (5)
"My mother and aunt LOVED the decor."
Pet-Friendly Bartlett Farmhouse w/ Deck!
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (42)
"Great house in a great locations. Beautiful backyard with ample room and swing set for the kids. The rooms are big with very comfortable beds. Love the house. "
Breathtaking home close to Schaumburg, Chicago
The Best of Wheaton, Family and Pet Friendly
9.8 out of 10, Exceptional, (8)
"This stay was quite special for us. We came to town for a Rottweiler dog show. When I was booking the house I found out who the owners mom was and how long she lived in the house. She was an icon in our breed. A true legend. having a huge yard for our dogs to play in after a long day at the dog show was wonderful. Bedrooms are very comfortable. The host is very accommodating and hospitable. Thank you Larry for everything "
The Best of Wheaton, Family and Pet Friendly
Geneva Island Park Retreat
10.0 out of 10, Exceptional, (22)
"Perfect home to accommodate our family. It’s a well appointed home, in a splendid location to walk to town. "
Geneva Island Park Retreat
The Main Event Game House on the Huntley Square!
9.6 out of 10, Exceptional, (9)
"I surprised my husband for his 40th with a getaway and invited his sisters, mom, and neices. We also have a 18month old who was with us. It was a great comfy house to stay in and great set up for eating and playing games together."
The price is £240
includes taxes & fees
4 Nov - 5 Nov
The Main Event Game House on the Huntley Square!
Great location-King beds-Kids playroom
10.0 out of 10, Exceptional, (16)
"Clean property with great amenities and outdoor space. Family friendly for my infant and toddler. Would stay here again if we're in the neighborhood."
Great location-King beds-Kids playroom
Glen Ellyn Country Side Home
9.2 out of 10, Wonderful, (16)
"Clean property, comfortable furniture and beds. Great pool! Communication with host was excellent. Would recommend!!"
Glen Ellyn Country Side Home
St. Charles Riverview Retreat
10.0 out of 10, Exceptional, (15)
"The house was super cute & clean. The host was very quick to respond to questions. Great location with plenty of food nearby. With traffic it was about an hour & 15 minute drive to downtown Chicago. Highly recommend "
The price is £360
includes taxes & fees
3 Nov - 4 Nov
St. Charles Riverview Retreat
PROMO 10% WEEKLY/12% MONTHLY DISCOUNT! King Bed, High-Speed WiFi, Large Deck
9.8 out of 10, Exceptional, (23)
"Excellent place to stay. Super comfortable home. Everything you might need is provided. Neighborhood is very nice and close to several parks and shopping centers. If you are planning to do a lot of things in downtown Chicago consider a 45min to 1hr drive each way."
The price is £264
includes taxes & fees
4 Nov - 5 Nov
PROMO 10% WEEKLY/12% MONTHLY DISCOUNT! King Bed, High-Speed WiFi, Large Deck
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
9.4 out of 10, Exceptional, (11)
"We stayed in Schaumburg for my son‘s wedding. The host was excellent with wonderful communication and the house was as described. It was clean and in a great location and we would definitely stay again."
The price is £341
includes taxes & fees
3 Nov - 4 Nov
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12
10.0 out of 10, Exceptional, (14)
"Three family’s came from 3 states for a wedding, and it was the perfect place for us to visit and enjoy one another! Thank you to the host who is terrific! "
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12
2 BR remodeled home near Cary/Crystal Lake/McHenry
9.6 out of 10, Exceptional, (33)
"This place was perfect for my husband, myself, and my mother. It was so cute and quaint. It reminded me of a nice little cottage in the woods. Where we live, we don’t have trees so having all of the grass and trees around was so refreshing! It’s not far from restaurants or grocery stores and depending on traffic not that far maybe an hour drive from Chicago."
2 BR remodeled home near Cary/Crystal Lake/McHenry
Log Cabin with HGTV Style Backyard INCREDIBLE property
8.2 out of 10, Very good, (18)
"We had an absolute blast during our stay here. The best place for a bachelor party getaway, a total and complete man cave in every way possible. We loved it and Larry was such an amazing host. He was very helpful and we can't wait to come back. We decided we are going to make this stay a yearly man trip with the guys."
Log Cabin with HGTV Style Backyard INCREDIBLE property
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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Other types of properties in Sleepy Hollow you may be interested in

Motel 6 Rolling Meadows, IL - Chicago Northwest
2.0 star property
6.6 out of 10, (1020)
"They have one hard working staff. Great job."
The price is £49
includes taxes & fees
4 Nov - 5 Nov
Motel 6 Rolling Meadows, IL - Chicago Northwest
Hyatt Regency Schaumburg Chicago
4.0 star property
8.2 out of 10, Very good, (1028)
"Beautiful lobby."
The price is £93
includes taxes & fees
3 Nov - 4 Nov
Hyatt Regency Schaumburg Chicago
Eaglewood Resort and Spa
4.0 star property
8.6 out of 10, Excellent, (1006)
"This was a really nice resort and me and my wife really enjoyed our birthdays I would recommend others to check it out "
The price is £117
includes taxes & fees
3 Nov - 4 Nov
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.

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?

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub: This holiday home rental outside of Sleepy Hollow offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 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 garden and a selection of games.

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 Hemmens Cultural Center and Grand Victoria Casino.

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.