Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

Cottage in Fox River Grove

10.0 out of 10, Exceptional, (16)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
United States
Kelly F.
The price is AU$316
includes taxes & fees
10 Dec - 11 Dec
Little Fox Cottage - A Cozy Riverview Getaway

Apartment in West Dundee

10.0 out of 10, Exceptional, (11)
"The loft is a great place to stay and we can’t wait to return! "
United States
Chad G.
The price is AU$325
includes taxes & fees
3 Dec - 4 Dec
Hip Urban Loft-Small Town Charm -124 LOFTS #4

Holiday Home in South Elgin

9.8 out of 10, Exceptional, (34)
"Luci was an excellent host and our stay was great!"
United States
Michelle C.
The price is AU$351
includes taxes & fees
1 Jan - 2 Jan 2026
Riverfront rental

Holiday Home in Cary

2.0 star property
The price is AU$599
includes taxes & fees
7 Dec - 8 Dec
King bed Crystal Lake Mchenry Cary Cozy

Cottage in St. Charles

3.0 star property
The price is AU$826
includes taxes & fees
3 Dec - 4 Dec
Fire Pit & Grill: Family Home on Fox River Trail!

Holiday Home in Carol Stream

9.6 out of 10, Exceptional, (4)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is AU$827
includes taxes & fees
3 Dec - 4 Dec
Beautiful House in Carol Stream near Downtown Chicago

Holiday Home in Woodstock

9.8 out of 10, Exceptional, (48)
"I really enjoyed the place "
United States
Ahmed A.
The price is AU$455
includes taxes & fees
9 Dec - 10 Dec
The Tailor House

Apartment in Barrington

9.6 out of 10, Exceptional, (5)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
United States
Sarah S.
The price is AU$201
includes taxes & fees
3 Dec - 4 Dec
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Apartment in West Dundee

10.0 out of 10, Exceptional, (12)
"Home away from home!!!"
United States
Tamera H.
The price is AU$391
includes taxes & fees
7 Dec - 8 Dec
Charming Downtown Farmhouse Apartment #4

Condo in Elk Grove Village

10.0 out of 10, Exceptional, (15)
"Location was close to airport, restaurants and shopping"
United States
Dorothy J.
The price is AU$391
includes taxes & fees
3 Dec - 4 Dec
Just remodeled apartment close to airport and mall

Holiday Home in Wheaton

10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is AU$476
includes taxes & fees
3 Dec - 4 Dec
✽ Charming Cottage ✽ close to College/Town/Station

Condo in Geneva

10.0 out of 10, Exceptional, (20)
"Beautiful place! Every detail was thought of for their guest!"
United States
Libby M.
The price is AU$384
includes taxes & fees
3 Dec - 4 Dec
- Beautiful Condo - King Bed - Free Waffle Breakfast -

Holiday Home in Bull Valley

10.0 out of 10, Exceptional, (7)
"The new place was amazing. I wished my work trip was longer so I could have stayed longer. The owner was also very responsive with messages and was great to talk to. I would definitely stay again the next time I'm in town. "
United States
Adam M.
The price is AU$456
includes taxes & fees
3 Dec - 4 Dec
Elegant New Home Near Lakes - Relax & Unwind!

Holiday Home in streamwood

10.0 out of 10, Exceptional, (2)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is AU$519
includes taxes & fees
3 Dec - 4 Dec
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

Apartment in Geneva

9.4 out of 10, Exceptional, (32)
"This is located in a nice quiet neighborhood. I felt safe taking walks at night by myself. We like the location. Close to stores, parks, bike paths, commuter train, and major roadsThe beds are comfortable, the kitchen has plenty of dishes & pots & pans. Everything was adequate for our needs. We'll stay here again the next time it works out!"
United States
Mary Ann V.
The price is AU$468
includes taxes & fees
3 Dec - 4 Dec
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Apartment in Geneva

9.6 out of 10, Exceptional, (7)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is AU$461
includes taxes & fees
3 Dec - 4 Dec
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Holiday Home in Geneva

10.0 out of 10, Exceptional, (37)
"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
- Fully-Equipped Condo - King Bed - Massive yard -

Holiday Home in Schaumburg

8.4 out of 10, Very good, (5)
"Had a wonderful relaxing & enjoyable stay; would definitely book again!"
United States
Chenae J.
The price is AU$835
includes taxes & fees
9 Dec - 10 Dec
4BR Near Woodfield Mall & Metra | LCP Collection

Holiday Home in Schaumburg

9.8 out of 10, Exceptional, (31)
"What a wonderful property! Roomy, clean, nicely decorated, and in a quiet and pleasant neighborhood. The back yard was awesome, large and fenced in but also lined with mature trees which provide privacy. The host was quickly responsive when messaged with questions."
United States
Jennifer S.
The price is AU$705
includes taxes & fees
3 Dec - 4 Dec
Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom

Apartment in Geneva

9.4 out of 10, Exceptional, (23)
"Great location for walking downtown and on 3rd street. Quiet, clean and nice touches. "
United States
Richard K.
The price is AU$433
includes taxes & fees
10 Dec - 11 Dec
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
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$201 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?

Spacious open concept home w/ game room + firepit: This holiday home rental outside of Sleepy Hollow offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and kitchenware, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Randall Oaks Golf Club and Hemmens Cultural Center.

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.