Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

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, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is HK$745
HK$1,342 total
includes taxes & fees
17 May - 18 May
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Exterior

Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is HK$1,374
HK$2,062 total
includes taxes & fees
18 May - 19 May
Little Fox Cottage - A Cozy Riverview Getaway
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, (16 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is HK$1,057
HK$1,960 total
includes taxes & fees
26 May - 27 May
Just remodeled apartment close to airport and mall
Smart TV, stereo

- 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 HK$987
HK$2,283 total
includes taxes & fees
19 May - 20 May
- 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, (27 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$916
HK$2,199 total
includes taxes & fees
19 May - 20 May
- Beautiful Condo - King Bed - Free Waffle Breakfast -
Interior

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (40 reviews)
"Luci was excellent. A quiet lovely house on the river. Thank you"
United States
Brian N.
The price is HK$1,370
HK$1,899 total
includes taxes & fees
21 May - 22 May
Riverfront rental
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (67 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is HK$1,370
HK$2,465 total
includes taxes & fees
31 May - 1 Jun
✽ Charming Cottage ✽ close to College/Town/Station
Exterior

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 HK$1,198
HK$2,207 total
includes taxes & fees
26 May - 27 May
The Tailor House
Smart TV, fireplace, offices

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 HK$1,907
HK$4,051 total
includes taxes & fees
18 May - 19 May
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
1 bedroom, desk, iron/ironing board, free WiFi

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 HK$1,225
HK$2,686 total
includes taxes & fees
8 Jun - 9 Jun
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Fridge, microwave, oven, stovetop

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 HK$673
HK$1,504 total
includes taxes & fees
18 May - 19 May
Chic 1BR Apt -Arlington Heights
Fridge, microwave, oven, stovetop

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Geneva
9.8 out of 10, Exceptional, (35 reviews)
"Great stay. Owner very easy to work with and place was clean. Would reccomend."
United States
Jason W.
The price is HK$1,127
HK$2,653 total
includes taxes & fees
20 May - 21 May
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Property grounds

Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (13 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
The price is HK$1,636
HK$2,057 total
includes taxes & fees
26 May - 27 May
Kildahl House - Boutique Farmhouse Suite #2
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
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 HK$2,106
HK$4,890 total
includes taxes & fees
18 May - 19 May
4BR Near Woodfield Mall & Metra | LCP Collection
1 bedroom, desk, iron/ironing board, WiFi

124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (21 reviews)
"We were in town visiting family and it was the perfect spot to stay for a day or two. We loved that it was right above a local cafe (which was also fantastic by the way!!), and the check-in/out process was a breeze! Owner was very communicative, would definitely stay here again!"
United States
Adamm I.
The price is HK$1,472
HK$1,840 total
includes taxes & fees
25 May - 26 May
124 Lofts #3 - Downtown Dundee - Walk to Dining
Games room

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 HK$1,073
HK$2,124 total
includes taxes & fees
18 May - 19 May
The Main Event Game House on the Huntley Square!
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, (9 reviews)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is HK$1,034
HK$2,507 total
includes taxes & fees
17 May - 18 May
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$1,186
HK$2,826 total
includes taxes & fees
20 May - 21 May
Spacious 3 Bedroom
Private kitchen

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 HK$2,161
HK$4,439 total
includes taxes & fees
28 May - 29 May
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Property grounds

Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (14 reviews)
"Everything was as described, great location too! "
United States
Freddy M.
The price is HK$1,636
HK$2,049 total
includes taxes & fees
21 May - 22 May
Kildahl House - Boutique Farmhouse Suite #1
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

Wingate by Wyndham Chicago Schaumburg

Wingate by Wyndham Chicago Schaumburg

8/10 Good
"."
Steve 1-night trip
Posted 2 hours ago
Wingate by Wyndham Chicago Schaumburg

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?

Breathtaking home close to Schaumburg, Chicago: This holiday home rental outside of Sleepy Hollow offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a terrace, a garden and a selection of games 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.