Holiday Rentals in Sleepy Hollow

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Holiday Rentals in Sleepy Hollow

Fox River Retreat

9.8 out of 10, Exceptional, (22)
"Convenient location "
Fox River Retreat

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (162)
"Very clean and well maintained. Would stay again for sure. "
Historic home with easy access to Chicago

Game room+King Bed+WiFi+Near Chicago & O’Hare

10.0 out of 10, Exceptional, (22)
"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 €427
includes taxes & fees
3 Dec - 4 Dec
Game room+King Bed+WiFi+Near Chicago & O’Hare

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (48)
"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

Comforting Retreat Near Woodfield Mall by RedAwning

9.4 out of 10, Exceptional, (10)
"Nice place to stay, will definitely stay again. "
Comforting Retreat Near Woodfield Mall by RedAwning

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, (43)
"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

Discover Wheaton's charm.

9.8 out of 10, Exceptional, (8)
"An exceptional place to stay. We felt very welcome. Plenty of room both indoors and out. Host is very responsive, respectful, and accommodating!"
Discover Wheaton's charm.

Riverfront rental with fun activities

10.0 out of 10, Exceptional, (22)
"Great place, awesome host. Would definitely recommend. "
The price is €220
includes taxes & fees
1 Dec - 2 Dec
Riverfront rental with fun activities

Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants

9.8 out of 10, Exceptional, (9)
"Super clean home with modern updates. Definitely a bonus with the fenced in yard for the dog. Nice neighborhood to walk the dog and admire the Halloween decorations."
Squeaky clean and cozy house, walk to AH downtown, fenced yard, pets, infants

Geneva Island Park Retreat

10.0 out of 10, Exceptional, (23)
"Perfect home to accommodate our family. It’s a well appointed home, in a splendid location to walk to town. "
Geneva Island Park Retreat

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

9.6 out of 10, Exceptional, (29)
"The spacious, well-maintained home was perfect for our group. The bedrooms were roomy, and the living areas provided plenty of space to relax and enjoy time together. The fully equipped kitchen made meal prep easy. A highlight was the neighboring estate with horses. The children loved it! The outdoor spaces were ideal for relaxation, with patios for morning coffee. Overall, this rental was the perfect setting for a memorable getaway. "
The price is €1,245
includes taxes & fees
27 Nov - 28 Nov
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Charming King Bed, Wi-Fi St. Charles

10.0 out of 10, Exceptional, (2)
"While the yard lacked care & maintenance the inside was super clean & provided many upscale features. Soft linens on firm beds, kitchen amenities with brand name, not generic, products. VRBO photos match - it is as shown."
The price is €557
includes taxes & fees
10 Dec - 11 Dec
Charming King Bed, Wi-Fi St. Charles

1Blk to 3rd st / Pets / 400Mb wifi, W&D, Free reserved parking!

9.2 out of 10, Wonderful, (9)
"It was quaint. Quiet neighborhood. Very close to tons of shopping and restaurants."
The price is €239
includes taxes & fees
3 Dec - 4 Dec
1Blk to 3rd st / Pets / 400Mb wifi, W&D, Free reserved parking!

The Main Event Game House on the Huntley Square!

9.6 out of 10, Exceptional, (10)
"We had an amazing time during our stay! The house had a lot of character with antique details, like an old record player, tv and radio. There were many modern updates as well. The kitchen seemed pretty new and all of the appliances worked great! The house was clean and there was a lot of attention to detail. The hot and cold water are flipped in the shower, so beware! It is an older house, so be prepared for occasional creaking and settling noises. The game room is detached from the house and in...
The price is €295
includes taxes & fees
2 Dec - 3 Dec
The Main Event Game House on the Huntley Square!

Great location-King beds-Kids playroom

10.0 out of 10, Exceptional, (17)
"We did enjoy our stay in this beautiful home. We had everything we needed to be comfortable. The location was perfect fou our needs."
Great location-King beds-Kids playroom

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

Spacious and comfortable 5 bedroom, 2 1/2 bath two miles from down town Geneva

8.8 out of 10, Excellent, (30)
"We enjoyed this lovely home in a wonderful area. We recommend visiting Geneva. It has a lot to see and do. "
Spacious and comfortable 5 bedroom, 2 1/2 bath two miles from down town Geneva

Basement Suite, Separate-entrance in Prime Location

8.0 out of 10, Very good, (2)
"This was listed as a full basement apartment, it was not it had a tiny sink smaller than a bathroom sink I had to bend down and was dishes in under another counter. There was only a hot plate to cook on. If I had known this I would have planned differently. Also it left a lot to be desired in the cleaning department. We found trash under the couch and cabinet in the bathroom. In the shower a dirty used bar of soap. The floors where sticky and dirty and made our feet and socks black. No wash...
The price is €149
includes taxes & fees
2 Dec - 3 Dec
Basement Suite, Separate-entrance in Prime Location

The Adorable "Blue Breeze"!

9.8 out of 10, Exceptional, (10)
"Thank you!!"
The Adorable "Blue Breeze"!
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

Country Inn & Suites by Radisson, Schaumburg, IL

3.0 star property
8.6 out of 10, Excellent, (1011)
"I highly recommend "
The price is €101
includes taxes & fees
22 Dec - 23 Dec
Country Inn & Suites by Radisson, Schaumburg, IL

Hyatt Regency Schaumburg Chicago

4.0 star property
8.2 out of 10, Very good, (1011)
"I really liked this hotel, the aesthetic during the holidays was for sure a bonus, 10/10 recommend "
The price is €118
includes taxes & fees
10 Dec - 11 Dec
Hyatt Regency Schaumburg Chicago

Motel 6 Rolling Meadows, IL - Chicago Northwest

2.0 star property
6.8 out of 10, (1032)
"Nothing to complain about with this motel 6. "
The price is €56
includes taxes & fees
19 Dec - 20 Dec
Motel 6 Rolling Meadows, IL - Chicago Northwest
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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Crystal Lake Park. 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.