Search Vacation Homes in Sleepy Hollow

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7
In one month
Dec 19 - Dec 21
In two months
Jan 16 - Jan 18

Vacation Homes in Sleepy Hollow

House
King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy

2.0 star property
Cary
$380 nightly
The price is $402
Nov 24 - Nov 25
Total with taxes and fees
King bed Crystal Lake Mchenry Cary Cozy
Fridge, microwave, oven, stovetop
Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom

Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom

Schaumburg
9.8 out of 10, Exceptional, (31)
"What a wonderful property! Roomy, clean, nicely decorated, and in a quiet and pleasant neighborhood. The back yard was awesome, large and fenced in but also lined with mature trees which provide privacy. The host was quickly responsive when messaged with questions."
United States
Jennifer S.
$427 nightly
The price is $457
Nov 23 - Nov 24
Total with taxes and fees
Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
$291 nightly
The price is $308
Nov 24 - Nov 25
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Paper towels, dining tables
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

streamwood
10.0 out of 10, Exceptional, (2)
"Was nice would recommend staying with you folks"
United States
Richard W.
$334 nightly
The price is $357
Nov 23 - Nov 24
Total with taxes and fees
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Exterior
The Tailor House

The Tailor House

Woodstock
9.8 out of 10, Exceptional, (48)
"I really enjoyed the place "
United States
Ahmed A.
$278 nightly
The price is $295
Dec 2 - Dec 3
Total with taxes and fees
The Tailor House
Fridge, microwave, oven, stovetop
Spacious Ranch blocks away from downtown McHenry

Spacious Ranch blocks away from downtown McHenry

McHenry
9.6 out of 10, Exceptional, (19)
"Great home and perfect location. "
United States
Steve B.
$309 nightly
The price is $327
Nov 23 - Nov 24
Total with taxes and fees
Spacious Ranch blocks away from downtown McHenry
Terrace/patio
Riverfront rental

Riverfront rental

South Elgin
9.8 out of 10, Exceptional, (34)
"Luci was an excellent host and our stay was great!"
United States
Michelle C.
$198 nightly
The price is $210
Nov 30 - Dec 1
Total with taxes and fees
Riverfront rental
Interior
The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!

Huntley
9.8 out of 10, Exceptional, (18)
"We loved our stay here, perfect for our family of five. My kids loved the game room! We will definitely be back next time we are in Huntley."
United States
Kristen D.
$279 nightly
The price is $296
Nov 24 - Nov 25
Total with taxes and fees
The Main Event Game House on the Huntley Square!
Fridge, microwave, oven, stovetop
Beautiful House in Carol Stream near Downtown Chicago

Beautiful House in Carol Stream near Downtown Chicago

Carol Stream
10.0 out of 10, Exceptional, (3)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
$546 nightly
The price is $578
Dec 1 - Dec 2
Total with taxes and fees
Beautiful House in Carol Stream near Downtown Chicago
Fridge, microwave, oven, stovetop
4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection

Schaumburg
8.4 out of 10, Very Good, (5)
"Had a wonderful relaxing & enjoyable stay; would definitely book again!"
United States
Chenae J.
$509 nightly
The price is $541
Dec 9 - Dec 10
Total with taxes and fees
4BR Near Woodfield Mall & Metra | LCP Collection
Fridge, microwave, oven, stovetop
Spacious 3 Bedroom

Spacious 3 Bedroom

2.0 star property
Cary
$296 nightly
The price is $314
Nov 29 - Nov 30
Total with taxes and fees
Spacious 3 Bedroom
Smart TV, books
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

2.0 star property
Schaumburg
10.0 out of 10, Exceptional, (2)
"Super comfy for families and the nicest host. "
United States
Anonymous traveler
$464 nightly
The price is $496
Dec 1 - Dec 2
Total with taxes and fees
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Interior
Family Heaven Retreat, 6 Bedroom, Sleep 16

Family Heaven Retreat, 6 Bedroom, Sleep 16

Carol Stream
9.6 out of 10, Exceptional, (7)
"Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! "
United States
Daniella S.
$681 nightly
The price is $722
Dec 16 - Dec 17
Total with taxes and fees
Family Heaven Retreat, 6 Bedroom, Sleep 16
Fridge, microwave, oven, stovetop
Relaxing Lake Zurich 3BR + Patio | LCP Collection

Relaxing Lake Zurich 3BR + Patio | LCP Collection

Lake Zurich
8.4 out of 10, Very Good, (5)
"Property was newly updated, was in a great location for us and met our needs. We had an issue with heating and owner resolved it. There were a few details that needed attended to, I discussed with owner and am confident that he was listening. Harry is very responsive. We would stay here again."
United States
Liz S.
$431 nightly
The price is $457
Dec 1 - Dec 2
Total with taxes and fees
Relaxing Lake Zurich 3BR + Patio | LCP Collection
Smart TV
Spacious A-Frame sleeps 25 on 5 wooded acres with a private fishing pond

Spacious A-Frame sleeps 25 on 5 wooded acres with a private fishing pond

McHenry
10.0 out of 10, Exceptional, (2)
"Great location and wonderful home! Perfect for our retreat."
United States
Lauren B.
$950 nightly
The price is $1,007
Nov 24 - Nov 25
Total with taxes and fees
Spacious A-Frame sleeps 25 on 5 wooded acres with a private fishing pond
2 bedrooms, iron/ironing board, WiFi, bed sheets
Basement Suite, Separate-entrance in Prime Location

Basement Suite, Separate-entrance in Prime Location

Schaumburg
6.8 out of 10, (6)
"The property was clean and what we needed for our trip. I would suggest adding some hand towels in the bathroom and dish towels or paper towels in the kitchen since it does provide an opportunity to cook. One bed was a little high for the vertically challenged! "
United States
Amy W.
$247 nightly
The price is $264
Nov 25 - Nov 26
Total with taxes and fees
Basement Suite, Separate-entrance in Prime Location
Property grounds
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

Arlington Heights
9.0 out of 10, Wonderful, (4)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
United States
James b.
$430 nightly
The price is $460
Nov 25 - Nov 26
Total with taxes and fees
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Interior
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

wheaton
$399 nightly
The price is $422
Nov 23 - Nov 24
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
Private kitchen
Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!

Elgin
10.0 out of 10, Exceptional, (1)
$1,028 nightly
The price is $1,089
Nov 23 - Nov 24
Total with taxes and fees
Modern Suburban Oasis- 14 guest House. Family Friendly!
A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

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

McHenry
9.2 out of 10, Wonderful, (41)
"Very comfortable… enjoyed the property to the upmost.."
United States
Debra H.
$1,153 nightly
The price is $1,222
Nov 24 - Nov 25
Total with taxes and fees
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sleepy Hollow Hotel Reviews

DoubleTree by Hilton Chicago - Arlington Heights

DoubleTree by Hilton Chicago - Arlington Heights

10/10 Excellent
"Nice clean facility "
Marty 1-night trip
Posted 3 days ago
DoubleTree by Hilton Chicago - Arlington Heights

Find out more about Sleepy Hollow

Sleepy Hollow Vacation Homes information

Number of reviews
274
Accommodation
168 Vacation Homes
Lowest Price
$210
Highest Price
$1,222

Explore a world of travel with Expedia