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Holiday Homes in Sleepy Hollow

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
9.4 out of 10, Exceptional, (3 reviews)
"Great place"
United States
Sthendall M.
The price is €298
includes taxes & fees
2 Nov - 3 Nov
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A modern living room with a dining area, a sofa, a TV, and a fireplace.

2. Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
Elgin
10.0 out of 10, Exceptional, (24 reviews)
"This was a great house with a beautiful property!"
United States
Malcolm S.
The price is €436
includes taxes & fees
21 Oct - 22 Oct
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
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 €233
includes taxes & fees
19 Oct - 20 Oct
The Main Event Game House on the Huntley Square!
A staircase with a wooden handrail and black metal railings, leading to an upper floor.

4. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (51 reviews)
"Incredible host and property."
United States
John V.
The price is €237
includes taxes & fees
1 Nov - 2 Nov
Riverfront rental
A wooden deck with a table and chairs, surrounded by lush greenery and trees.

5. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
9.4 out of 10, Exceptional, (3 reviews)
"Nice quiet spot to rest a Travelers head"
United States
Dan K.
The price is €273
includes taxes & fees
19 Oct - 20 Oct
Spacious 3 Bedroom
A lakeside deck with chairs and a table, a wooden dock extending into the water, and a covered area in the background.

6. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
The price is €557
includes taxes & fees
3 Nov - 4 Nov
Waterfront - Private Dock - Two Suites
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

7. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is €389
includes taxes & fees
20 Oct - 21 Oct
King bed Crystal Lake Mchenry Cary Cozy
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

8. 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.
The price is €326
includes taxes & fees
2 Nov - 3 Nov
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
A sectional sofa with a glass coffee table in a sunroom with large windows.

9. 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 €860
includes taxes & fees
19 Oct - 20 Oct
Modern Suburban Oasis- 14 guest House. Family Friendly!
A covered porch with wicker furniture, a coffee table, and a potted plant.

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (47 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
The price is €250
includes taxes & fees
20 Oct - 21 Oct
- Fully-Equipped Condo - King Bed - Massive yard -
A modern TopGolf facility with a prominent entrance, multiple levels, and a parking area.

11. Game Room Getaway Near O’Hare

Game Room Getaway Near O’Hare
Schaumburg
9.6 out of 10, Exceptional, (36 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
The price is €362
includes taxes & fees
19 Oct - 20 Oct
Game Room Getaway Near O’Hare
A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

12. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (57 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
The price is €231
includes taxes & fees
22 Oct - 23 Oct
The Tailor House
A Cadillac SUV parked on a paved driveway with a gated entrance, surrounded by trees with autumn foliage.

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

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is €3,321
includes taxes & fees
19 Oct - 20 Oct
Perfect Family Getaway: Spacious 5BR Home in Barrington
A two-story house with a swimming pool, outdoor seating, and a stone chimney.

14. 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, (47 reviews)
"This place was amazing. We had a large group and it did not disappoint. The place was clean and well stocked. The host was so accommodating and the communication was great. We would stay here again for sure."
United States
Darlene C.
The price is €1,240
includes taxes & fees
20 Oct - 21 Oct
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A modern living room with a sofa, chairs, and a coffee table.

15. Family Home, Fire Pit, Pool Table • Near Woodfield

Family Home, Fire Pit, Pool Table • Near Woodfield
Schaumburg
9.8 out of 10, Exceptional, (28 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 €399
includes taxes & fees
26 Oct - 27 Oct
Family Home, Fire Pit, Pool Table • Near Woodfield
Private kitchen

16. 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
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
A modern living room with a sofa, a coffee table, and a view of the outdoors.

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

Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg
10.0 out of 10, Exceptional, (11 reviews)
"Super comfy for families and the nicest host. "
United States
Anonymous traveller
The price is €519
includes taxes & fees
19 Oct - 20 Oct
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

18. 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, (13 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is €336
includes taxes & fees
27 Oct - 28 Oct
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
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 building with a sign reading 'Hale Street Cantina' and a brick facade.

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

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (74 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is €295
includes taxes & fees
29 Oct - 30 Oct
✽ Charming Cottage ✽ close to College/Town/Station
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 Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

10/10 Excellent
"Muy bien todo"
Derling isacio 3-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

Find out more about Sleepy Hollow

Sleepy Hollow Holiday Homes information

Number of reviews
415
Accommodation
182 Holiday Homes
Lowest Price
€231
Highest Price
€3,321

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