Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Sleepy Hollow holiday rentals

Smart TV

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, (7 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 HK$985
HK$1,597 total
includes taxes & fees
12 Feb - 13 Feb
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Outdoor dining

Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
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 HK$985
HK$1,582 total
includes taxes & fees
16 Feb - 17 Feb
Little Fox Cottage - A Cozy Riverview Getaway
1 bedroom, desk, iron/ironing board, WiFi

Hip Urban Loft-Small Town Charm - 124 LOFTS #3

Hip Urban Loft-Small Town Charm - 124 LOFTS #3
West Dundee
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 HK$977
HK$1,651 total
includes taxes & fees
12 Feb - 13 Feb
Hip Urban Loft-Small Town Charm - 124 LOFTS #3
2 bedrooms

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is HK$939
HK$3,616 total
includes taxes & fees
15 Feb - 16 Feb
King bed Crystal Lake Mchenry Cary Cozy
Dining tables

Elegant New Home Near Lakes - Relax & Unwind!

Elegant New Home Near Lakes - Relax & Unwind!
Bull Valley
10.0 out of 10, Exceptional, (7 reviews)
"Everything was really good"
United States
Jeff H.
The price is HK$1,043
HK$2,174 total
includes taxes & fees
21 Feb - 22 Feb
Elegant New Home Near Lakes - Relax & Unwind!
Fridge, microwave, oven, stovetop

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (49 reviews)
"I really enjoyed the place "
United States
Ahmed A.
The price is HK$1,032
HK$2,171 total
includes taxes & fees
12 Feb - 13 Feb
The Tailor House
Interior

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (35 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 HK$1,016
HK$1,648 total
includes taxes & fees
12 Feb - 13 Feb
Riverfront rental
Paper towels

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (15 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is HK$1,055
HK$1,998 total
includes taxes & fees
21 Feb - 22 Feb
Just remodeled apartment close to airport and mall
Smart TV, books

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)
"We had a great stay in Geneva for the night. Our spot was very convenient to lots of places around town. I would definitely recommend staying at this location! "
United States
jennifer f.
The price is HK$649
HK$2,139 total
includes taxes & fees
15 Feb - 16 Feb
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Terrace/patio

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
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 HK$704
HK$1,972 total
includes taxes & fees
16 Feb - 17 Feb
- Fully-Equipped Condo - King Bed - Massive yard -
Terrace/patio

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (20 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 HK$985
HK$2,312 total
includes taxes & fees
22 Feb - 23 Feb
- Beautiful Condo - King Bed - Free Waffle Breakfast -
TV, offices

Charming Downtown Farmhouse Apartment #3

Charming Downtown Farmhouse Apartment #3
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"This apartment is beautiful, gorgeously furnished and spotlessly clean. Good location, easy access and lovely hosts. Wonderful stay, highly recommended."
United States
Lesley K.
Charming Downtown Farmhouse Apartment #3
Smart TV, fireplace, books

Family Heaven Retreat, 6 Bedroom, Sleep 16

Family Heaven Retreat, 6 Bedroom, Sleep 16
Carol Stream
9.6 out of 10, Exceptional, (7 reviews)
"Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! "
United States
Daniella S.
The price is HK$1,152
HK$5,138 total
includes taxes & fees
12 Feb - 13 Feb
Family Heaven Retreat, 6 Bedroom, Sleep 16
Fridge, microwave, oven, stovetop

Cozy & Serene 1BR Escape

Cozy & Serene 1BR Escape
Arlington Heights
7.6 out of 10, Good, (7 reviews)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
The price is HK$617
HK$1,438 total
includes taxes & fees
2 Mar - 3 Mar
Cozy & Serene 1BR Escape
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 reviews)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is HK$985
HK$2,651 total
includes taxes & fees
15 Feb - 16 Feb
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
TV

Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake Elegance: Serene 2BR Townhome Retreat
Wonder Lake
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
The price is HK$1,043
HK$2,174 total
includes taxes & fees
15 Feb - 16 Feb
Wonder Lake Elegance: Serene 2BR Townhome Retreat
Smart TV

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, (8 reviews)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is HK$977
HK$2,458 total
includes taxes & fees
22 Feb - 23 Feb
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Outdoor dining

Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
The price is HK$809
HK$2,373 total
includes taxes & fees
23 Feb - 24 Feb
Spacious 3 Bedroom
Smart TV

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, (23 reviews)
"Great location for walking downtown and on 3rd street. Quiet, clean and nice touches. "
United States
Richard K.
The price is HK$774
HK$2,200 total
includes taxes & fees
15 Feb - 16 Feb
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Interior

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)
"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.
The price is HK$1,125
HK$3,102 total
includes taxes & fees
12 Feb - 13 Feb
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

Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

10/10 Excellent
"Was very nice "
Madilene 3-night trip
Posted 2 days ago
Hyatt Place Chicago/Hoffman Estates

Find out more about Sleepy Hollow

Search for holiday rentals in Sleepy Hollow on Expedia! You can easily find your home rentals, villas, holiday apartments in Sleepy Hollow using one of the methods below:

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Look no further and take a look at our great range of rental properties in Sleepy Hollow!

Frequently asked questions

Are there holiday rentals in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. Sleepy Hollow is known for its bars.

What are some of the best holiday rentals that Sleepy Hollow has to offer?

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub: This holiday home rental outside of Sleepy Hollow is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area, you’ll find Hemmens Cultural Center and Grand Victoria Casino.

What’s a holiday rental in Sleepy Hollow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sleepy Hollow. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.