Sleepy Hollow Vacation Rentals

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Our top choices for Sleepy Hollow vacation rentals

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is CA $130
CA $234 total
includes taxes & fees
May 11 - May 12
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Cozy & Serene 1BR Escape

Cozy & Serene 1BR Escape
Arlington Heights
7.6 out of 10, Good, (8 reviews)
"Comfortable stay; great communication"
United States
Alyssa
The price is CA $138
CA $291 total
includes taxes & fees
May 13 - May 14
Cozy & Serene 1BR Escape

- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (39 reviews)
"We really enjoyed our stay here. The kitchen had everything we needed and the house was very nice. Finding the driveway was a bit tricky in the dark. Thank you for a welcoming place to call home while we were in town for a wedding. "
United States
Cathy
The price is CA $142
CA $365 total
includes taxes & fees
May 11 - May 12
- Fully-Equipped Condo - King Bed - Massive yard -

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is CA $146
CA $498 total
includes taxes & fees
May 11 - May 12
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Geneva
9.4 out of 10, Exceptional, (24 reviews)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
United States
Jerilynn L.
The price is CA $157
CA $411 total
includes taxes & fees
May 11 - May 12
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights
Arlington Heights
8.0 out of 10, Very good, (1 review)
"Parking was a problem "
United States
Brian W.
The price is CA $131
CA $282 total
includes taxes & fees
May 13 - May 14
Chic 1BR Apt -Arlington Heights

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Geneva
9.4 out of 10, Exceptional, (33 reviews)
"The host was very welcoming "
United States
Karen B.
The price is CA $184
CA $461 total
includes taxes & fees
May 11 - May 12
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (65 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is CA $233
CA $428 total
includes taxes & fees
May 11 - May 12
✽ Charming Cottage ✽ close to College/Town/Station

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (39 reviews)
"Luci was excellent. A quiet lovely house on the river. Thank you"
United States
Brian N.
The price is CA $239
CA $338 total
includes taxes & fees
May 11 - May 12
Riverfront rental

The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is CA $187
CA $375 total
includes taxes & fees
May 11 - May 12
The Main Event Game House on the Huntley Square!

Relaxing Lake Zurich 3BR + Patio | LCP Collection

Relaxing Lake Zurich 3BR + Patio | LCP Collection
Lake Zurich
8.8 out of 10, Excellent, (6 reviews)
"This was by far the cleanest VRBO we have rented. The location was perfect for our visit. The fully fenced yard was great for our dogs. The host promptly responded to questions I had prior to and during our stay. "
United States
diana w.
The price is CA $246
CA $619 total
includes taxes & fees
May 11 - May 12
Relaxing Lake Zurich 3BR + Patio | LCP Collection

Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
10.0 out of 10, Exceptional, (1 review)
The price is CA $957
CA $1,325 total
includes taxes & fees
May 11 - May 12
Modern Suburban Oasis- 14 guest House. Family Friendly!

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (51 reviews)
"I really enjoyed the place "
United States
Ahmed A.
The price is CA $189
CA $365 total
includes taxes & fees
May 12 - May 13
The Tailor House

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
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
The price is CA $246
CA $621 total
includes taxes & fees
May 11 - May 12
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

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, (43 reviews)
"The house was beautifully clean and spacious. It was the perfect size for our family group and pets. Great location as well.Our host was very accommodating, highly recommended!"
United States
Kathe L.
The price is CA $518
CA $1,701 total
includes taxes & fees
May 12 - May 13
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Recharge in This Charming 1BR Apt

Recharge in This Charming 1BR Apt
Arlington Heights
8.0 out of 10, Very good, (1 review)
"Cute and cozy. Easy access with parking"
United States
Jenna R.
The price is CA $137
CA $287 total
includes taxes & fees
May 17 - May 18
Recharge in This Charming 1BR Apt

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Geneva
9.6 out of 10, Exceptional, (9 reviews)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is CA $181
CA $439 total
includes taxes & fees
May 18 - May 19
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Game Room - Arcade & King Bed | LCP Collection

Game Room - Arcade & King Bed | LCP Collection
Streamwood
9.0 out of 10, Wonderful, (2 reviews)
"it is a nice & quiet home & area . host is nice & responds in a timely manner . "
United States
Ashley A.
The price is CA $294
CA $683 total
includes taxes & fees
May 13 - May 14
Game Room - Arcade & King Bed | LCP Collection

Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.8 out of 10, Excellent, (3 reviews)
"Cute and cozy little house. Convenient location. I would stay there again if the need ever comes up again. "
United States
holly g.
The price is CA $231
CA $403 total
includes taxes & fees
May 11 - May 12
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

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, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is CA $237
CA $597 total
includes taxes & fees
May 11 - May 12
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
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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Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sleepy Hollow. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Sleepy Hollow?

Yes, we offer vacation rentals near popular local attractions in Sleepy Hollow, or you can go with a secluded option if you want a relaxing place to stay. Sleepy Hollow is known for its bars.

What's the top vacation rental that Sleepy Hollow has to offer?

Breathtaking home close to Schaumburg, Chicago: This vacation home rental outside of Sleepy Hollow offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Elgin Sports Complex. In the larger area, you’ll find Hemmens Cultural Center and Grand Victoria Casino.

What’s a vacation rental in Sleepy Hollow like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Sleepy Hollow. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.