Book Holiday Homes in Sleepy Hollow

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Featured Holiday Homes in Sleepy Hollow

Historic home with easy access to Chicago

Historic home with easy access to Chicago

Glen Ellyn
A stay at this vacation home places you in the heart of Glen Ellyn, within a 5-minute drive of Wheaton College and Billy Graham Center Museum.
Historic home with easy access to Chicago
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Schaumburg
With a stay at this vacation home in Schaumburg, you'll be within a 10-minute drive of Woodfield Mall and Schaumburg Convention Center.
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
Geneva Island Park Retreat

Geneva Island Park Retreat

Geneva
With a stay at this vacation home in Geneva, you'll be within a 15-minute walk of Island Park and C'est La Vie.
Geneva Island Park Retreat
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HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

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

McHenry
The price is AU$2,070 per night from 28 Apr to 29 Apr
AU$2,070
includes taxes & fees
28 Apr - 29 Apr
When you stay at this vacation home in McHenry, you'll be within a 10-minute drive of McHenry City Hall and McHenry Shores Beach Park.
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Beautiful 5 bedroom home on private lake

Beautiful 5 bedroom home on private lake

Mundelein
Located in Lake Zurich, this vacation home is within a 10-minute drive of Steeple Chase and Breezewald Park.
Beautiful 5 bedroom home on private lake
Comforting Retreat Near Woodfield Mall by RedAwning

Comforting Retreat Near Woodfield Mall by RedAwning

Rolling Meadows
With a stay at this vacation home in Rolling Meadows, you'll be within a 10-minute drive of Woodfield Mall and Schaumburg Convention Center.
Comforting Retreat Near Woodfield Mall by RedAwning
Breathtaking home close to Schaumburg, Chicago

Breathtaking home close to Schaumburg, Chicago

Palatine
With a stay at this vacation home in Schaumburg, you'll be within a 5-minute drive of Schaumburg Convention Center and Woodfield Mall.
Breathtaking home close to Schaumburg, Chicago
Bliss in Batavia near the Fox River

Bliss in Batavia near the Fox River

Batavia
The price is AU$820 per night from 24 Apr to 25 Apr
AU$820
includes taxes & fees
24 Apr - 25 Apr
With a stay at this vacation home in Batavia, you'll be within a 5-minute drive of Water Street Studios Gallery and Batavia Depot Museum.
Bliss in Batavia near the Fox River
Charming 3-bedroom/ 2 Bath Single Family Home/ Schaumburg

Charming 3-bedroom/ 2 Bath Single Family Home/ Schaumburg

Schaumburg
With a stay at this vacation home in Schaumburg, you'll be within a 15-minute drive of Woodfield Mall and Schaumburg Convention Center.
Charming 3-bedroom/ 2 Bath Single Family Home/ Schaumburg
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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.

Sleepy Hollow Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Sleepy Hollow vacation homes are the perfect way for you to wing it.

Holiday houses in Sleepy Hollow let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Sleepy Hollow in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Sleepy Hollow adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Sleepy Hollow with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Sleepy Hollow vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Sleepy Hollow Holiday Homes essential information

Accommodation
180 Holiday Homes
Lowest Price
AU$164
Highest Price
AU$2,070
Popular accommodation
Historic home with easy access to Chicago, Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard, Geneva Island Park Retreat, HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub, Beautiful 5 bedroom home on private lake , Comforting Retreat Near Woodfield Mall by RedAwning, Breathtaking home close to Schaumburg, Chicago, Bliss in Batavia near the Fox River, Charming 3-bedroom/ 2 Bath Single Family Home/ Schaumburg

Top trending hotels in Sleepy Hollow

Hyatt Regency Schaumburg Chicago

Hyatt Regency Schaumburg Chicago

4 out of 5
1800 East Golf Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is AU$213 per night from 27 Apr to 28 Apr
AU$213
includes taxes & fees
27 Apr - 28 Apr
When you stay at Hyatt Regency Schaumburg Chicago in Schaumburg, you'll be in the business district, within a 5-minute drive of Woodfield Mall and Schaumburg ...
Hyatt Regency Schaumburg Chicago
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 30 Apr to 1 May
AU$167
includes taxes & fees
30 Apr - 1 May
When you stay at Hyatt Place Chicago/Hoffman Estates in Hoffman Estates, you'll be in the business district, within a 5-minute drive of Arboretum of South Barrington ...
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Itasca

Hyatt Place Itasca

3 out of 5
1150 North Arlington Heights Road, Itasca, IL
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 1 May to 2 May
AU$164
includes taxes & fees
1 May - 2 May
When you stay at Hyatt Place Itasca in Itasca, you'll be in the business district, within a 15-minute drive of Woodfield Mall and Schaumburg Convention ...
Hyatt Place Itasca
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DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 2 May to 3 May
AU$175
includes taxes & fees
2 May - 3 May
Located in Wood Dale, DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove is in the suburbs, within a 15-minute drive of LEGOLAND® Discovery Center and ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Don't see what you're looking for?
See all available properties in Sleepy Hollow
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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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^Subject to availability and chosen travel dates.