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

TV, offices
Sunny 1BR Apartment in the Surburbs

Sunny 1BR Apartment in the Surburbs

Sunny 1BR Apartment in the Surburbs
Arlington Heights
5.4 out of 10, (3)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
The price is HK$467
HK$1,259 total
includes taxes & fees
16 Dec - 17 Dec
Sunny 1BR Apartment in the Surburbs
Outdoor dining
Chicago-burb -Medinah -1 King and 1 Queen beds

Chicago-burb -Medinah -1 King and 1 Queen beds

Chicago-burb -Medinah -1 King and 1 Queen beds
Medinah
9.6 out of 10, Exceptional, (33)
"Everything was pretty convenient and was comfortable for our long stay in the town. "
United States
Mansoor M.
Chicago-burb -Medinah -1 King and 1 Queen beds
A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
McHenry
9.2 out of 10, Wonderful, (42)
"The property management team, maintenance and cleaning staff are excellent. Communication was thorough and response time was quick. We enjoyed the pool very much."
United States
Allison K.
The price is HK$1,938
HK$8,317 total
includes taxes & fees
15 Dec - 16 Dec
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
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
Terrace/patio
- 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 -
Property grounds
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
Interior
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

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (4)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
United States
James b.
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
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
Fridge, microwave, oven, stovetop
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
Glen Ellyn
10.0 out of 10, Exceptional, (31)
"Great house, great neighborhood, host was amazing!"
United States
John B.
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
Outdoor dining
Breathtaking home close to Schaumburg, Chicago

Breathtaking home close to Schaumburg, Chicago

Breathtaking home close to Schaumburg, Chicago
Palatine
9.8 out of 10, Exceptional, (77)
"Great comfortable spot near the city"
United States
Jacob M.
Breathtaking home close to Schaumburg, Chicago
Smart TV, fireplace
Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,

Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,

Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,
Roselle
10.0 out of 10, Exceptional, (4)
"Thank you for a great stay and accommodating our group!"
United States
Jay P.
Luxury 5BR Family Getaway – Heated Pool, Hot Tub, Fire pit, Game Room,
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
Private kitchen
Spacious Family & Pet-Friendly Getaway in Lake in the Hills

Spacious Family & Pet-Friendly Getaway in Lake in the Hills

Spacious Family & Pet-Friendly Getaway in Lake in the Hills
Lake in the Hills
9.0 out of 10, Wonderful, (4)
"There is a big backyard that our dog absolutely enjoyed! The house was spacious and clean!! "
United States
Donna K.
Spacious Family & Pet-Friendly Getaway in Lake in the Hills
Interior
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage

The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage

The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
Arlington Heights
10.0 out of 10, Exceptional, (1)
The Vail/House/Hot Tub/Fire pit/Tesla charger/Garage
Smart TV, table football, ping pong
Charming 4 Bedroom home in the heart of Elgin

Charming 4 Bedroom home in the heart of Elgin

Charming 4 Bedroom home in the heart of Elgin
Elgin
9.4 out of 10, Exceptional, (38)
"Very clean, great space, will definitely stay again when in Elgin! "
United States
Jenifer V.
Charming 4 Bedroom home in the heart of Elgin
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
Interior
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!
Exterior
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
Barrington
The price is HK$7,785
HK$52,241 total
includes taxes & fees
15 Dec - 16 Dec
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True
6 bedrooms, iron/ironing board, travel cot, WiFi
Minutes to Downtown Saint Charles, Cozy/Chic Home

Minutes to Downtown Saint Charles, Cozy/Chic Home

Minutes to Downtown Saint Charles, Cozy/Chic Home
St. Charles
9.6 out of 10, Exceptional, (12)
"We had a very nice stay at this property. Farrah was easy to work with on entrance into the property, etc. "
United States
Ed S.
Minutes to Downtown Saint Charles, Cozy/Chic Home
Terrace/patio
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago

Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago

Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago
Schaumburg
10.0 out of 10, Exceptional, (13)
"This was a great place to hang out with friends and our family. A nice selection of sleeping space, a big table to eat or play games together inside, and a well equipped kitchen.We especially enjoyed the backyard- pictures and descriptions are accurate. With the pool, grill, and multiple seating options, it was a great place to have some fun and hang out and visit. We highly recommend staying here!"
United States
Brenda R.
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago
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
  • Use the map to find apartments and other holiday homes in the Sleepy Hollow neighbourhood you prefer
  • 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.