Sleepy Hollow Vacation Rentals

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Our top choices for Sleepy Hollow vacation 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, (7 reviews)
"Barrington was an adorable town tucked away just an hour out of Chicago. This property is the perfect spot for a getaway with your loved one. My boyfriend and I had an amazing weekend and will definitely stop by again in the future!"
United States
Cierra F.
$196 nightly
The price is $210
Jan 17 - Jan 18
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
$394 nightly
The price is $417
Jan 20 - Jan 21
Total with taxes and fees
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)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
United States
Kelly F.
$202 nightly
The price is $214
Jan 19 - Jan 20
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (49 reviews)
"I really enjoyed the place "
United States
Ahmed A.
$262 nightly
The price is $278
Jan 19 - Jan 20
Total with taxes and fees
The Tailor House

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.
$222 nightly
The price is $235
Jan 23 - Jan 24
Total with taxes and fees
Elegant New Home Near Lakes - Relax & Unwind!

Hip Urban Loft-Small Town Charm -124 LOFTS #4

Hip Urban Loft-Small Town Charm -124 LOFTS #4
West Dundee
10.0 out of 10, Exceptional, (13 reviews)
"The loft is a great place to stay and we can’t wait to return! "
United States
Chad G.
$195 nightly
The price is $211
Jan 18 - Jan 19
Total with taxes and fees
Hip Urban Loft-Small Town Charm -124 LOFTS #4

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful place! Every detail was thought of for their guest!"
United States
Libby M.
$235 nightly
The price is $249
Jan 19 - Jan 20
Total with taxes and fees
- Beautiful Condo - King Bed - Free Waffle Breakfast -

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, (32 reviews)
"Loved the nice touches like water purification pitcher and white noise machine. Comfy beds too!"
United States
Dan M.
$246 nightly
The price is $272
Jan 17 - Jan 18
Total with taxes and fees
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Beautiful House in Carol Stream near Downtown Chicago

Beautiful House in Carol Stream near Downtown Chicago
Carol Stream
9.6 out of 10, Exceptional, (4 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
$461 nightly
The price is $489
Jan 19 - Jan 20
Total with taxes and fees
Beautiful House in Carol Stream near Downtown Chicago

Charming Downtown Farmhouse Apartment #2

Charming Downtown Farmhouse Apartment #2
West Dundee
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed the property and the location."
United States
Matthew L.
$226 nightly
The price is $244
Jan 18 - Jan 19
Total with taxes and fees
Charming Downtown Farmhouse Apartment #2

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.
$253 nightly
The price is $279
Jan 19 - Jan 20
Total with taxes and fees
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.4 out of 10, Very Good, (5 reviews)
"Had a wonderful relaxing & enjoyable stay; would definitely book again!"
United States
Chenae J.
$461 nightly
The price is $490
Jan 20 - Jan 21
Total with taxes and fees
4BR Near Woodfield Mall & Metra | LCP Collection

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
wheaton
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
$402 nightly
The price is $426
Jan 20 - Jan 21
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (34 reviews)
"Luci was an excellent host and our stay was great!"
United States
Michelle C.
$194 nightly
The price is $206
Jan 18 - Jan 19
Total with taxes and fees
Riverfront rental

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (56 reviews)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
$291 nightly
The price is $308
Jan 19 - Jan 20
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station

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.
$282 nightly
The price is $311
Jan 18 - Jan 19
Total with taxes and fees
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

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.
$237 nightly
The price is $254
Jan 18 - Jan 19
Total with taxes and fees
Just remodeled apartment close to airport and mall

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.
$644 nightly
The price is $683
Jan 19 - Jan 20
Total with taxes and fees
Family Heaven Retreat, 6 Bedroom, Sleep 16

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.
$155 nightly
The price is $168
Feb 2 - Feb 3
Total with taxes and fees
Cozy & Serene 1BR Escape

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.
$361 nightly
The price is $386
Jan 18 - Jan 19
Total with taxes and fees
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $168 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation 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 vacation.

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 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?

Chicago-burb -Medinah -1 King and 1 Queen beds: This vacation home rental outside of Sleepy Hollow offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.