Search Vacation Homes in Sleepy Hollow

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 139 Vacation Homes in Sleepy Hollow with updated reviews, rates, and availability.

Fox River Retreat
9.8 out of 10, Exceptional, (20)
"Overall nice place on the Fox River for a weekend getaway. Location is a short drive to downtown St Charles and Geneva. "
Fox River 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 SAR 548
SAR 1,127 total
includes taxes & fees
13 Nov - 14 Nov
The Main Event Game House on the Huntley Square!
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
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
Great location-King beds-Kids playroom
10.0 out of 10, Exceptional, (17)
"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
Chicago&O’Hare/King Bed/Fenced yard/Game room
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 SAR 828
SAR 1,629 total
includes taxes & fees
10 Nov - 11 Nov
Chicago&O’Hare/King Bed/Fenced yard/Game room
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (36)
"We had a great stay in this lovely home close to Wheaton College. Everything was very clean and the kitchen was well equipped. Easy access/check-in, parking and the house was very pleasantly decorated. Thank you!"
The price is SAR 639
SAR 1,089 total
includes taxes & fees
19 Nov - 20 Nov
✽ Charming Cottage ✽ close to College/Town/Station
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.
The Tailor House
10.0 out of 10, Exceptional, (38)
"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 SAR 496
SAR 1,016 total
includes taxes & fees
11 Nov - 12 Nov
The Tailor House
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
10.0 out of 10, Exceptional, (21)
"Stayed here with my immediate family for my mother-in-law's memorial service and couldn't have been more pleased. Well maintained property in the perfect location for our needs."
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
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
- Fully-Equipped Condo - King Bed - Massive yard -
10.0 out of 10, Exceptional, (20)
"Everything was perfect! I stayed with my friends and had a girls night before my wedding. We had plenty of room and enjoyed the waffles and coffee for breakfast. "
The price is SAR 470
SAR 1,082 total
includes taxes & fees
12 Nov - 13 Nov
- Fully-Equipped Condo - King Bed - Massive yard -
Historic Glen Ellyn Home with "Optional" Carriage House
2.5 star property
Historic Glen Ellyn Home with "Optional" Carriage House
The Carol Stream Casa - Luxury Large Home, King Bed, 75"/65" TVs, Workspace
2.0 star property
The Carol Stream Casa - Luxury Large Home, King Bed, 75"/65" TVs, Workspace
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
Historic home with easy access to Chicago
9.8 out of 10, Exceptional, (161)
"The house was perfect and our host was wonderful."
Historic home with easy access to Chicago
Comforting Retreat Near Woodfield Mall by RedAwning
9.4 out of 10, Exceptional, (9)
"Property was exactly as advertised! Property Manager Michael was fast and prompt, and helpful, with keypad issue at the house! Very comfy place, Thank you so much!"
Comforting Retreat Near Woodfield Mall by RedAwning
Fox Valley Farmhouse Overlooking The Fox River!
10.0 out of 10, Exceptional, (31)
"An amazing property. Totally remodeled. Beautifully appointed! Location was perfect close to Geneva and St Charles. Super clean "
Fox Valley Farmhouse Overlooking The Fox River!
Bliss in Batavia near the Fox River
9.6 out of 10, Exceptional, (13)
"Very cozy house, amazing family neighborhood. Yes we were about an hour away from Chicago but it was worth it. For the tranquility the house gave. Would recommend! "
The price is SAR 1,428
SAR 2,560 total
includes taxes & fees
25 Nov - 26 Nov
Bliss in Batavia near the Fox River
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.
Don't see what you're looking for?
See all available properties in Sleepy Hollow
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Sleepy Hollow

The Tailor House
10.0 out of 10, Exceptional, (38)
"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 SAR 496
SAR 1,016 total
includes taxes & fees
11 Nov - 12 Nov
The Tailor House
Chicago&O’Hare/King Bed/Fenced yard/Game room
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 SAR 828
SAR 1,629 total
includes taxes & fees
10 Nov - 11 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 SAR 1,845
SAR 5,148 total
includes taxes & fees
12 Nov - 13 Nov
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
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.