Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Sleepy Hollow vacation rentals

House | 2 bedrooms

Vacation Home in Cary

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
The price is ￥17,252
￥70,525 total
includes taxes & fees
Mar 1 - Mar 2
King bed Crystal Lake Mchenry Cary Cozy
Smart TV

Apartment in Barrington

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
9.8 out of 10, Exceptional, (8 reviews)
"Nice little spot in the NW Suburbs. Great jumping off point for everything further North and points South."
United States
Thomas Z.
The price is ￥14,730
￥26,598 total
includes taxes & fees
Mar 2 - Mar 3
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Outdoor dining

Cottage in Fox River Grove

Little Fox Cottage - A Cozy Riverview Getaway
10.0 out of 10, Exceptional, (17 reviews)
"Cute and efficient house to stay. Communication was perfect. The property had everything we needed including walking distance to the Ski Lodge. Would definitely stay here again. "
United States
Antje K.
The price is ￥21,042
￥33,368 total
includes taxes & fees
Mar 1 - Mar 2
Little Fox Cottage - A Cozy Riverview Getaway
Paper towels

Condo in Elk Grove Village

Just remodeled apartment close to airport and mall
10.0 out of 10, Exceptional, (15 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is ￥21,042
￥39,519 total
includes taxes & fees
Mar 4 - Mar 5
Just remodeled apartment close to airport and mall
Fridge, microwave, oven, stovetop

Apartment in Arlington Heights

Cozy & Serene 1BR Escape
7.6 out of 10, Good, (7 reviews)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
The price is ￥14,652
￥31,910 total
includes taxes & fees
Mar 3 - Mar 4
Cozy & Serene 1BR Escape
Fridge, microwave, oven, stovetop

Vacation Home in Woodstock

The Tailor House
9.8 out of 10, Exceptional, (49 reviews)
"I really enjoyed the place "
United States
Ahmed A.
The price is ￥20,575
￥43,279 total
includes taxes & fees
Mar 1 - Mar 2
The Tailor House
Fridge, microwave, oven, stovetop

Vacation Home in Schaumburg

4BR Near Woodfield Mall & Metra | LCP Collection
8.4 out of 10, Very Good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is ￥24,472
￥75,172 total
includes taxes & fees
Mar 1 - Mar 2
4BR Near Woodfield Mall & Metra | LCP Collection
Interior

Vacation Home in South Elgin

Riverfront rental
9.8 out of 10, Exceptional, (36 reviews)
"Impressive AirBb our host really knock it out of the park..Thank you we will definitely be stay again.."
United States
Josh R.
The price is ￥23,381
￥35,681 total
includes taxes & fees
Mar 1 - Mar 2
Riverfront rental

Apartment in West Dundee

Hip Urban Loft-Small Town Charm - 124 LOFTS #3
10.0 out of 10, Exceptional, (21 reviews)
"We have stayed at this property several times and have always had a great experience. The loft is spacious, convenient and comfortable!"
United States
Jen C.
The price is ￥19,484
￥33,085 total
includes taxes & fees
Mar 1 - Mar 2
Hip Urban Loft-Small Town Charm - 124 LOFTS #3
Terrace/patio

Vacation Home in Geneva

- Fully-Equipped Condo - King Bed - Massive yard -
10.0 out of 10, Exceptional, (37 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 ￥13,888
￥38,835 total
includes taxes & fees
Mar 4 - Mar 5
- Fully-Equipped Condo - King Bed - Massive yard -
Outdoor dining

Vacation Home in Wheaton

✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (58 reviews)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is ￥26,498
￥48,070 total
includes taxes & fees
Mar 9 - Mar 10
✽ Charming Cottage ✽ close to College/Town/Station
TV

Condo in Wonder Lake

Wonder Lake Elegance: Serene 2BR Townhome Retreat
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
The price is ￥28,876
￥56,867 total
includes taxes & fees
Mar 1 - Mar 2
Wonder Lake Elegance: Serene 2BR Townhome Retreat
Outdoor dining

Vacation Home in Cary

Spacious 3 Bedroom
The price is ￥16,125
￥47,319 total
includes taxes & fees
Mar 1 - Mar 2
Spacious 3 Bedroom

Apartment in West Dundee

Charming Downtown Farmhouse Apartment #2
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
The price is ￥21,822
￥38,087 total
includes taxes & fees
Mar 6 - Mar 7
Charming Downtown Farmhouse Apartment #2
Fridge, microwave, oven, stovetop

Apartment in Arlington Heights

Recharge in This Charming 1BR Apt
The price is ￥14,652
￥31,576 total
includes taxes & fees
Mar 2 - Mar 3
Recharge in This Charming 1BR Apt
Fridge, microwave, oven, stovetop

Vacation Home in Batavia

Bliss in Batavia near the Fox River
9.8 out of 10, Exceptional, (27 reviews)
"Cute house, great yard and neighborhood, and host was very responsive."
United States
Shannon V.
The price is ￥35,694
￥78,632 total
includes taxes & fees
Mar 2 - Mar 3
Bliss in Batavia near the Fox River
Smart TV

Apartment in Geneva

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
9.4 out of 10, Exceptional, (23 reviews)
"Great location for walking downtown and on 3rd street. Quiet, clean and nice touches. "
United States
Richard K.
The price is ￥15,431
￥43,043 total
includes taxes & fees
Mar 8 - Mar 9
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Exterior

Vacation Home in Schaumburg

Near Chicago and O’Hare +Fenced yard +Game room+New Bath!
9.6 out of 10, Exceptional, (33 reviews)
"We came from Florida to visit family. This house was exactly what we were looking for. Kids loved the game room. Beautiful backyard and comfortable beds. Will stay again. "
United States
Mary M.
The price is ￥34,354
￥71,602 total
includes taxes & fees
Mar 1 - Mar 2
Near Chicago and O’Hare +Fenced yard +Game room+New Bath!
Microwave, oven, stovetop, dishwasher

Vacation Home in Bull Valley

BRAND NEW 3-bedroom, 2.5 bath townhome with 70 inch TV
BRAND NEW 3-bedroom, 2.5 bath townhome with 70 inch TV
Terrace/patio

Condo in Geneva

- Beautiful Condo - King Bed - Free Waffle Breakfast -
10.0 out of 10, Exceptional, (21 reviews)
"We had a lovely stay! The property was well appointed and comfortable. The host was very responsive. "
United States
Kathryn M.
The price is ￥21,042
￥46,748 total
includes taxes & fees
Mar 12 - Mar 13
- Beautiful Condo - King Bed - Free Waffle Breakfast -
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

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

10/10 Excellent
"Staff was amazing and very accommodating. Definitely recommend "
Chantel 1-night trip
Posted 2 days ago
Comfort Inn & Suites Arlington Heights - Schaumburg

Find out more about Sleepy Hollow

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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?

Riverfront rental: This vacation home rental outside of Sleepy Hollow is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.