Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday rentals

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 AU$264
includes taxes & fees
27 Apr - 28 Apr
Cozy & Serene 1BR Escape

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, (8 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is AU$242
includes taxes & fees
22 Apr - 23 Apr
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

- 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 AU$371
includes taxes & fees
20 Apr - 21 Apr
- Fully-Equipped Condo - King Bed - Massive yard -

Recharge in This Charming 1BR Apt

Recharge in This Charming 1BR Apt
Arlington Heights
8.0 out of 10, Very good, (1 review)
"Cute and cozy. Easy access with parking"
United States
Jenna R.
The price is AU$278
includes taxes & fees
30 Apr - 1 May
Recharge in This Charming 1BR Apt

- 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 AU$355
includes taxes & fees
20 Apr - 21 Apr
- Beautiful Condo - King Bed - Free Waffle Breakfast -

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is AU$649
includes taxes & fees
21 Apr - 22 Apr
King bed Crystal Lake Mchenry Cary Cozy

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 AU$288
includes taxes & fees
21 Apr - 22 Apr
Little Fox Cottage - A Cozy Riverview Getaway

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 AU$362
includes taxes & fees
20 Apr - 21 Apr
The Tailor House

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 AU$455
includes taxes & fees
19 Apr - 20 Apr
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

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 AU$264
includes taxes & fees
27 Apr - 28 Apr
Chic 1BR Apt -Arlington Heights

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 AU$447
includes taxes & fees
19 Apr - 20 Apr
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
9.8 out of 10, Exceptional, (19 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 AU$365
includes taxes & fees
19 Apr - 20 Apr
The Main Event Game House on the Huntley Square!

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 AU$731
includes taxes & fees
22 Apr - 23 Apr
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

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 AU$448
includes taxes & fees
21 Apr - 22 Apr
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

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 AU$289
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 AU$353
includes taxes & fees
1 May - 2 May
Just remodeled apartment close to airport and mall

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 AU$598
includes taxes & fees
20 Apr - 21 Apr
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

✽ 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 AU$423
includes taxes & fees
6 May - 7 May
✽ Charming Cottage ✽ close to College/Town/Station

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 AU$726
includes taxes & fees
20 Apr - 21 Apr
4BR Near Woodfield Mall & Metra | LCP Collection

Basement Suite, Separate-entrance in Prime Location

Basement Suite, Separate-entrance in Prime Location
Schaumburg
6.8 out of 10, (6 reviews)
"The property was clean and what we needed for our trip. I would suggest adding some hand towels in the bathroom and dish towels or paper towels in the kitchen since it does provide an opportunity to cook. One bed was a little high for the vertically challenged! "
United States
Amy W.
The price is AU$373
includes taxes & fees
19 Apr - 20 Apr
Basement Suite, Separate-entrance in Prime Location
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 favourite 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 depend 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 AU$289 per night. Entering your travel dates in the search wizard might find you 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.