Holiday Homes in Sleepy Hollow

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Featured Holiday Homes in Sleepy Hollow and around

Charming 3-bedroom house just minutes from Downtown Wheaton!

Charming 3-bedroom house just minutes from Downtown Wheaton!

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

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.

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

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

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

Cheerful 2 bedroom townhouse with free parking.

Cheerful 2 bedroom townhouse with free parking.

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

10.0 out of 10, Exceptional, (16)
"Exactly what we expected. Excellent place to stay"
Home w/ Office + Yard: 25 Mi to Downtown Chicago!

Cozy 4-bedroom house , 3-full baths in marvelous West Chicago with WiFi, AC,

2.0 star property
Cozy 4-bedroom house , 3-full baths in marvelous West Chicago with WiFi, AC,

Spacious 4BR Family retreat w/ Backyard Oasis in Schaumburg

Spacious 4BR Family retreat w/ Backyard Oasis in Schaumburg

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

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

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
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 property types 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
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.