Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Sleepy Hollow holiday rentals

1 bedroom, desk, iron/ironing board, WiFi
Hip Urban Loft-Small Town Charm -124 LOFTS #4

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, (11)
"The loft is a great place to stay and we can’t wait to return! "
United States
Chad G.
The price is HK$973
HK$1,644 total
includes taxes & fees
12 Jan - 13 Jan 2026
Hip Urban Loft-Small Town Charm -124 LOFTS #4
Terrace/patio
Riverfront rental

Riverfront rental

Riverfront rental
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 HK$1,012
HK$1,642 total
includes taxes & fees
15 Dec - 16 Dec
Riverfront rental
Paper towels
Just remodeled apartment close to airport and mall

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)
"Location was close to airport, restaurants and shopping"
United States
Dorothy J.
The price is HK$1,051
HK$1,974 total
includes taxes & fees
15 Dec - 16 Dec
Just remodeled apartment close to airport and mall
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

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (6)
"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 HK$981
HK$1,674 total
includes taxes & fees
26 Dec - 27 Dec
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (55)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is HK$1,323
HK$2,426 total
includes taxes & fees
16 Dec - 17 Dec
✽ Charming Cottage ✽ close to College/Town/Station
Property grounds
Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (17)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
United States
Kelly F.
The price is HK$1,323
HK$2,005 total
includes taxes & fees
6 Jan - 7 Jan 2026
Little Fox Cottage - A Cozy Riverview Getaway
Smart TV, fireplace, video games, table football
3BR House with Pickleball, Game Room, Foosball, Arcade, Cereal Bar, Darts &Grill

3BR House with Pickleball, Game Room, Foosball, Arcade, Cereal Bar, Darts &Grill

3BR House with Pickleball, Game Room, Foosball, Arcade, Cereal Bar, Darts &Grill
Lake Zurich
10.0 out of 10, Exceptional, (5)
"Very great stay. The home is perfect for a small family. Walking distance to 2 nice parks/playgrounds. Home has everything you need. Would stay again!"
United States
Michael R.
The price is HK$1,401
HK$3,350 total
includes taxes & fees
15 Dec - 16 Dec
3BR House with Pickleball, Game Room, Foosball, Arcade, Cereal Bar, Darts &Grill
Smart TV
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

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, (31)
"Extremely clean and updated apartment. Enjoyed our stay, would book this apartment again."
United States
Bryan R.
The price is HK$740
HK$2,046 total
includes taxes & fees
15 Dec - 16 Dec
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Fridge, microwave, oven, stovetop
Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom

Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom

Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom
Schaumburg
9.6 out of 10, Exceptional, (32)
"We came from Florida to visit family. This house was exactly what we were looking for. Kids loved the game room. Beautiful backyard and comfortable beds. Will stay again. "
United States
Mary M.
The price is HK$1,382
HK$3,169 total
includes taxes & fees
15 Dec - 16 Dec
Chicago&O’Hare! King Bed+WiFi+Deck&Fence. New Bathroom
Fridge, microwave, oven, stovetop
Spacious Ranch blocks away from downtown McHenry

Spacious Ranch blocks away from downtown McHenry

Spacious Ranch blocks away from downtown McHenry
McHenry
9.6 out of 10, Exceptional, (21)
"Great home and perfect location. "
United States
Steve B.
The price is HK$1,752
HK$2,549 total
includes taxes & fees
15 Dec - 16 Dec
Spacious Ranch blocks away from downtown McHenry
Fridge, microwave, oven, stovetop
Beautiful House in Carol Stream near Downtown Chicago

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)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is HK$2,170
HK$5,385 total
includes taxes & fees
20 Dec - 21 Dec
Beautiful House in Carol Stream near Downtown Chicago
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

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
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 HK$771
HK$2,087 total
includes taxes & fees
6 Jan - 7 Jan 2026
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Private kitchen
Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
10.0 out of 10, Exceptional, (1)
The price is HK$2,725
HK$4,216 total
includes taxes & fees
15 Dec - 16 Dec
Modern Suburban Oasis- 14 guest House. Family Friendly!
Smart TV, books
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
2.0 star property
Schaumburg
10.0 out of 10, Exceptional, (4)
"Home was as pictured, nice and cozy, very spacious. The bedrooms were really nice and spacious with TVs in each bedroom, bathroom was very spacious , All in all the home was AWESOME! And if I’m going to be in the area again, I’d Book this home again!"
United States
Tiffany T.
The price is HK$2,522
HK$4,039 total
includes taxes & fees
15 Dec - 16 Dec
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
TV
Elegant New Home Near Lakes - Relax & Unwind!

Elegant New Home Near Lakes - Relax & Unwind!

Elegant New Home Near Lakes - Relax & Unwind!
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 HK$994
HK$2,110 total
includes taxes & fees
15 Dec - 16 Dec
Elegant New Home Near Lakes - Relax & Unwind!
Exterior
The Tailor House

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (48)
"I really enjoyed the place "
United States
Ahmed A.
The price is HK$1,028
HK$2,161 total
includes taxes & fees
17 Dec - 18 Dec
The Tailor House
Fridge, microwave, oven, stovetop
Bliss in Batavia near the Fox River

Bliss in Batavia near the Fox River

Bliss in Batavia near the Fox River
Batavia
9.8 out of 10, Exceptional, (25)
"Very clean, comfortable and well maintained."
United States
Volana M.
The price is HK$1,822
HK$3,944 total
includes taxes & fees
15 Dec - 16 Dec
Bliss in Batavia near the Fox River
3 bedrooms, desk, iron/ironing board, travel cot
- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
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 HK$1,518
HK$2,921 total
includes taxes & fees
13 Jan - 14 Jan 2026
- Beautiful Condo - King Bed - Free Waffle Breakfast -
Fridge, microwave, oven, stovetop
- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
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
The price is HK$1,557
HK$2,937 total
includes taxes & fees
31 Dec - 1 Jan 2026
- Fully-Equipped Condo - King Bed - Massive yard -
TV
Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake Elegance: Serene 2BR Townhome Retreat
Wonder Lake
10.0 out of 10, Exceptional, (2)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
The price is HK$994
HK$2,110 total
includes taxes & fees
15 Dec - 16 Dec
Wonder Lake Elegance: Serene 2BR Townhome Retreat
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

Eaglewood Resort and Spa

Eaglewood Resort and Spa

10/10 Excellent
"Clean room, good breakfast, quite and comfortable environment "
Olaoluwa 1-night trip
Posted 3 days ago
Eaglewood Resort and Spa

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:

  • View our selection of featured holiday rentals in Sleepy Hollow
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  • Enter your travel dates to view the best deals on holiday rentals in Sleepy Hollow while they last

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?

Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago: This holiday home rental outside of Sleepy Hollow offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 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 patio, 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 Three Oaks Recreation Area. 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.