Sleepy Hollow Vacation Rentals

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Check prices for these dates

Tonight
Jun 24 - Jun 25
Tomorrow
Jun 25 - Jun 26
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Sleepy Hollow

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Bar (on property)

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

6.8 out of 10, (3)
"Room clean, fitness room awful!! Have to request house keeping but they do not change sheets. Bar and restaurant bare minimum. They have a nice bar next to hotel(Not the-one located in the hotel) Would not stay again!"
The price is ￥12,986
￥16,063 total
includes taxes & fees
Jun 30 - Jul 1
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay
Fridge, microwave, oven, stovetop

3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay

7.6 out of 10, Good, (5)
"Wonderful neighborhood! Comfortable beds! Great TV in the living room. Communication with host was fabulous. "
The price is ￥43,043
￥63,324 total
includes taxes & fees
Jun 26 - Jun 27
3-bedroom house in awesome Addison with WiFi, AC. Enjoy your stay
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
2 bedrooms, desk, iron/ironing board, travel crib

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

9.6 out of 10, Exceptional, (25)
"Great location. Well kept and more spacious then expected. "
The price is ￥14,591
￥43,124 total
includes taxes & fees
Jul 7 - Jul 8
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Chicago-burb -Medinah -1 King and 1 Queen beds
Terrace/patio

Chicago-burb -Medinah -1 King and 1 Queen beds

9.4 out of 10, Exceptional, (22)
"The property was very clean and comfortable!"
Chicago-burb -Medinah -1 King and 1 Queen beds
Spacious Ranch blocks away from downtown McHenry
Fridge, microwave, oven, stovetop

Spacious Ranch blocks away from downtown McHenry

10.0 out of 10, Exceptional, (11)
"Very nice place and host is great "
The price is ￥35,748
￥40,417 total
includes taxes & fees
Jul 20 - Jul 21
Spacious Ranch blocks away from downtown McHenry
Minutes to Downtown Saint Charles, Cozy/Chic Home
TV

Minutes to Downtown Saint Charles, Cozy/Chic Home

10.0 out of 10, Exceptional, (7)
"Perfect location Very clean house and lots of rooms"
Minutes to Downtown Saint Charles, Cozy/Chic Home
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
Fridge, microwave, stovetop, dishwasher

Hot Tub & Sauna: Hoffman Estates Villa in Elgin!

10.0 out of 10, Exceptional, (2)
"The place was gorgeous and the property manager was amazing. Lots of space and great location. Everyone had room to move. We all had a great time. Thank you very much."
Hot Tub & Sauna: Hoffman Estates Villa in Elgin!
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (44)
"House is super clean, pictures are accurate. Would stay again! "
The price is ￥24,805
￥42,460 total
includes taxes & fees
Jun 30 - Jul 1
✽ Charming Cottage ✽ close to College/Town/Station
Breathtaking home close to Schaumburg, Chicago
Dining

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (58)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago
"St Geneva" Private With River View! 10 min to Lamplight Equestrian Center
Property grounds

"St Geneva" Private With River View! 10 min to Lamplight Equestrian Center

10.0 out of 10, Exceptional, (75)
"Michael was a great host. The property was very clean. The beds were very comfortable. The sculpture park across the street along the river was wonderful for walks in the evening. There are also other quaint cities near by to see."
"St Geneva" Private With River View! 10 min to Lamplight Equestrian Center
Just remodeled apartment close to airport and mall
Private kitchen

Just remodeled apartment close to airport and mall

10.0 out of 10, Exceptional, (11)
"The location was great for my purposes, nice apartment, great neighborhood and close to the airport."
The price is ￥19,567
￥34,694 total
includes taxes & fees
Jul 3 - Jul 4
Just remodeled apartment close to airport and mall
Riverfront rental
Terrace/patio

Riverfront rental

9.8 out of 10, Exceptional, (28)
"Impressive AirBb our host really knock it out of the park..Thank you we will definitely be stay again.."
The price is ￥24,075
￥35,113 total
includes taxes & fees
Jun 29 - Jun 30
Riverfront rental
New! Spacious Home 6BD/3BTH - Sleeps 16! in Hoffman Estates!
Living area

New! Spacious Home 6BD/3BTH - Sleeps 16! in Hoffman Estates!

10.0 out of 10, Exceptional, (1)
"Everything clean , good communication after booking , good location, etc, …its all good!"
New! Spacious Home 6BD/3BTH - Sleeps 16! in Hoffman Estates!
"Spacious 2BR Retreat with Office, Stunning Backyard & Grill in Hanover Park"
Property grounds

"Spacious 2BR Retreat with Office, Stunning Backyard & Grill in Hanover Park"

6.0 out of 10, (3)
"We booked this VRBO for a trip to Chicago with five mid-20 year-old men. We walked in and the home looked fine. It was adequately clean. There were, however, a few very bad things about this VRBO that make it unfit to stay in. 1. The actual beds are awful. Very thin mattresses and the box springs don't stay on the frames, they slide off and start to fall down. There were no sleeping pillows provided, only the decorative pillows that you would normally take off the bed.2. The futon is worse. I...
"Spacious 2BR Retreat with Office, Stunning Backyard & Grill in Hanover Park"
Spacious open concept home w/ game room + firepit
Microwave, dishwasher, coffee/tea maker, toaster

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (64)
"Excellent place to stay with a large family gathering!!! "
Spacious open concept home w/ game room + firepit
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (4)
"The place was just like it was described and it’s pictures. Clean, cozy, and in a nice quiet area. Would stay again! "
The price is ￥16,050
￥43,270 total
includes taxes & fees
Jun 26 - Jun 27
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
3BR House w/ Paradise Garden Oasis and private pool in the heart of Schaumburg
Property grounds

3BR House w/ Paradise Garden Oasis and private pool in the heart of Schaumburg

10.0 out of 10, Exceptional, (5)
"Great location, not far from some of the must sees in and out of the Chicago area. The backyard is awesome, it unfortunately snowed during our stay but during the summer months, you wouldn’t need to leave. The kids loved the themed rooms and all the Coca Cola things. Quiet neighborhood, owner was very responsive to questions, we would stay again!"
3BR House w/ Paradise Garden Oasis and private pool in the heart of Schaumburg
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (25)
"Home was in a quiet & friendly neighborhood with easy access to everything."
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard
Schaumburg Pool House
Outdoor pool, a heated pool

Schaumburg Pool House

10.0 out of 10, Exceptional, (14)
"A great location absolutely loved the house "
Schaumburg Pool House
The Carol Stream Casa - Luxury Large Home, 7 bds, 75" and 65" TVs, Workspace
Fridge, microwave, oven, stovetop

The Carol Stream Casa - Luxury Large Home, 7 bds, 75" and 65" TVs, Workspace

2.0 star property
6.4 out of 10, (5)
"Very beautiful,quiet area could not have asked for better we enjoyed our stay"
The Carol Stream Casa - Luxury Large Home, 7 bds, 75" and 65" TVs, Workspace
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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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?

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg ": This vacation home rental outside of Sleepy Hollow is equipped with an outdoor pool, air-conditioning, and a Smart TV to help you feel comfortable during your stay. It has 25 bedrooms as well as a kitchen with a fridge, a microwave, and a coffee maker, so you can cook with friends or family.

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 Randall Oaks Golf Club and Hemmens Cultural Center.

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.