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Holiday Homes in Sleepy Hollow

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Sleepy Hollow holiday homes

A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

1. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
8.0 out of 10, Very good, (1 review)
"Everything was great except not enough pots n pans and ac unit is very loud."
United States
Phuong N.
The price is €298
includes taxes & fees
31 Aug - 1 Sept
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

2. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (48 reviews)
"Cozy home, perfect for a relaxting time away "
United States
Phoenicia
The price is €234
includes taxes & fees
10 Sept - 11 Sept
Riverfront rental
A two-story house with a front porch, a stone exterior on the right side, and a green door.

3. The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 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 €235
includes taxes & fees
2 Sept - 3 Sept
The Main Event Game House on the Huntley Square!
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

4. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is €394
includes taxes & fees
31 Aug - 1 Sept
King bed Crystal Lake Mchenry Cary Cozy
A wooden deck with a table and chairs, surrounded by lush greenery and trees.

5. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
8.0 out of 10, Very good, (1 review)
"Conveniently located near restaurants and downtown. Apartment was clean. Nicely decorated. Cute coffee station. Big table in dining area."
United States
Kim B.
The price is €297
includes taxes & fees
23 Aug - 24 Aug
Spacious 3 Bedroom
A modern living room with a sofa, chairs, and a coffee table.

6. InstaWorthy! Modern Gem, Perfect Family Getaway-Pet Friendly!

InstaWorthy! Modern Gem, Perfect Family Getaway-Pet Friendly!
Schaumburg
9.8 out of 10, Exceptional, (27 reviews)
"Cozy atmosphere, great kitchen. Very much enjoyed the fact that there was a grill and fireplace. Will definitely recommend this place to people looking to visit the area. "
United States
Luke K.
The price is €410
includes taxes & fees
24 Aug - 25 Aug
InstaWorthy! Modern Gem, Perfect Family Getaway-Pet Friendly!
A covered porch with wicker furniture, a coffee table, and a potted plant.

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (45 reviews)
"Great place, well appointed, worked well for our needs!! Host was very responsive to any questions/requests. "
United States
Amy C.
The price is €279
includes taxes & fees
25 Aug - 26 Aug
- Fully-Equipped Condo - King Bed - Massive yard -
A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

8. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is €244
includes taxes & fees
24 Aug - 25 Aug
The Tailor House
A modern TopGolf facility with a prominent entrance, multiple levels, and a parking area.

9. Chicago&O’Hare+King Bed+WiFi+Deck&Fence

Chicago&O’Hare+King Bed+WiFi+Deck&Fence
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
The price is €399
includes taxes & fees
8 Sept - 9 Sept
Chicago&O’Hare+King Bed+WiFi+Deck&Fence
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. 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.
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
A flat-screen TV mounted on a wall displaying a streaming service interface with various channels and apps.

11. Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.4 out of 10, Exceptional, (6 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is €465
includes taxes & fees
26 Aug - 27 Aug
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
A sectional sofa with a glass coffee table in a sunroom with large windows.

12. Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
6.0 out of 10, (2 reviews)
The price is €844
includes taxes & fees
21 Sept - 22 Sept
Modern Suburban Oasis- 14 guest House. Family Friendly!
A living room with two grey sofas, a glass coffee table, a TV mounted on the wall, a potted plant, and a fireplace.

13. Family Heaven Retreat, 6 Bedroom, Sleep 16

Family Heaven Retreat, 6 Bedroom, Sleep 16
Carol Stream
9.6 out of 10, Exceptional, (8 reviews)
"Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! "
United States
Daniella S.
Family Heaven Retreat, 6 Bedroom, Sleep 16
A modern living room with a sofa, a coffee table, and a view of the outdoors.

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

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg
9.8 out of 10, Exceptional, (9 reviews)
"Super comfy for families and the nicest host. "
United States
Anonymous traveller
The price is €485
includes taxes & fees
25 Aug - 26 Aug
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
A building with a sign reading "Hale Street Cantina" and a brick facade.

15. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is €284
includes taxes & fees
6 Sept - 7 Sept
✽ Charming Cottage ✽ close to College/Town/Station
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

16. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.6 out of 10, Excellent, (10 reviews)
"It was very conveniently located"
United States
Rita L.
The price is €252
includes taxes & fees
24 Aug - 25 Aug
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
A Cadillac SUV parked on a paved driveway with a gated entrance, surrounded by trees with autumn foliage.

17. Perfect Family Getaway: Spacious 5BR Home in Barrington

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is €3,198
includes taxes & fees
23 Aug - 24 Aug
Perfect Family Getaway: Spacious 5BR Home in Barrington

18. Charming 2-bedroom house with WiFi, AC in fabulous Woodstock

Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
Woodstock
8.0 out of 10, Very good, (1 review)
"I was very surprised that the property was by itself on a 2 lane road. We initially drove past it because there was nothing on the side of the road with the address. It was next to an odd and ugly"building." It was less than 10 minutes frim town, which was good. The house was clean, but REEKED of mildew. We bought stuff to help with the smell (which we left for future guests), but it was still bad. There was no toaster or microwave, and there was someone elase's Culver's in the freezer....
United States
Anonymous traveller
The price is €325
includes taxes & fees
5 Sept - 6 Sept
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

19. 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
6.0 out of 10, (2 reviews)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
A dining area with a wooden table set for four, surrounded by grey armchairs. A large abstract painting is on the wall, and a potted plant is visible in the background.

20. Stylish Escape/Game Room/4 Brs

Stylish Escape/Game Room/4 Brs
Arlington Heights
9.4 out of 10, Exceptional, (16 reviews)
"Great place to stay in a great neighborhood."
United States
Sam M.
The price is €679
includes taxes & fees
7 Sept - 8 Sept
Stylish Escape/Game Room/4 Brs
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

DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

10/10 Excellent
"The staff were great. The hotel was undergoing renovations. The restarant was closed, but they had a makeshift one. The food in the makeshift one was very good. Housekeeping was excellent, so the room was very clean."
Batbara 3-night trip
Posted less than an hour ago
DoubleTree by Hilton Libertyville - Mundelein

Find out more about Sleepy Hollow

Sleepy Hollow Holiday Homes information

Number of reviews
265
Accommodation
182 Holiday Homes
Lowest Price
€234
Highest Price
€3,198

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