Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday 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 NZ$290
includes taxes & fees
22 Apr - 23 Apr
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (62 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is NZ$514
includes taxes & fees
22 Apr - 23 Apr
✽ Charming Cottage ✽ close to College/Town/Station

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)
"Host and amenities were great!"
United States
Jeff P.
The price is NZ$416
includes taxes & fees
26 Apr - 27 Apr
Little Fox Cottage - A Cozy Riverview Getaway

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 NZ$344
includes taxes & fees
23 Apr - 24 Apr
Riverfront rental

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 NZ$458
includes taxes & fees
8 May - 9 May
Just remodeled apartment close to airport and mall

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 NZ$720
includes taxes & fees
23 Apr - 24 Apr
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

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 NZ$886
includes taxes & fees
27 Apr - 28 Apr
4BR Near Woodfield Mall & Metra | LCP Collection

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 NZ$434
includes taxes & fees
26 Apr - 27 Apr
The Tailor House

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 NZ$329
includes taxes & fees
27 Apr - 28 Apr
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 NZ$480
includes taxes & fees
27 Apr - 28 Apr
- Fully-Equipped Condo - King Bed - Massive yard -

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.6 out of 10, Exceptional, (5 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is NZ$887
includes taxes & fees
6 May - 7 May
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

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 NZ$512
includes taxes & fees
22 Apr - 23 Apr
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Bliss in Batavia near the Fox River

Bliss in Batavia near the Fox River
Batavia
9.8 out of 10, Exceptional, (29 reviews)
"Cute house, great yard and neighborhood, and host was very responsive."
United States
Shannon V.
The price is NZ$839
includes taxes & fees
22 Apr - 23 Apr
Bliss in Batavia near the Fox River

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is NZ$756
includes taxes & fees
4 May - 5 May
King bed Crystal Lake Mchenry Cary Cozy

Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
Kildahl House - Boutique Farmhouse Suite #2

124 Lofts - Downtown Dundee - Walk to Dining

124 Lofts - Downtown Dundee - Walk to Dining
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 NZ$401
includes taxes & fees
5 May - 6 May
124 Lofts - Downtown Dundee - Walk to Dining

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (25 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 NZ$452
includes taxes & fees
27 Apr - 28 Apr
- Beautiful Condo - King Bed - Free Waffle Breakfast -

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 NZ$521
includes taxes & fees
22 Apr - 23 Apr
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

Spacious Ranch blocks away from downtown McHenry

Spacious Ranch blocks away from downtown McHenry
McHenry
9.6 out of 10, Exceptional, (24 reviews)
"Great home and perfect location. "
United States
Steve B.
The price is NZ$868
includes taxes & fees
2 May - 3 May
Spacious Ranch blocks away from downtown McHenry

124 Lofts - Downtown Dundee - Walk to Dining

124 Lofts - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. The loft is situated in an area where it is easy to walk to interesting dining options and stroll the river walk."
United States
Angela D.
The price is NZ$375
includes taxes & fees
22 Apr - 23 Apr
124 Lofts - Downtown Dundee - Walk to Dining
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

Everything you need to know about Sleepy Hollow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sleepy Hollow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sleepy Hollow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sleepy Hollow holiday rentals we have selected for you start as low as NZ$290 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Riverfront rental: This holiday home rental outside of Sleepy Hollow is located on a river, and has a patio, a garden and a BBQ 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 holiday with amenities such as 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 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.