Default HTG hotel image

Holiday Homes in Sleepy Hollow

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Sleepy Hollow holiday homes

Smart TV, fireplace, offices

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, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is €479
includes taxes & fees
29 Jun - 30 Jun
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Terrace/patio

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

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (41 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 €272
includes taxes & fees
28 Jun - 29 Jun
- Fully-Equipped Condo - King Bed - Massive yard -
Outdoor dining

Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
The price is €306
includes taxes & fees
28 Jun - 29 Jun
Spacious 3 Bedroom
Interior

Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay near St. Charles/Geneva. Will definitely stay again next time we visit. Plenty of room, great view, super easy access to west suburbs, North Ave./Randal Rd,/25/31, but tucked away from the hustle and bustle etc. Host was great, respected our privacy. Super hot shower! "
United States
Elsa L.
The price is €213
includes taxes & fees
20 Jul - 21 Jul
Riverfront rental
House

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is €413
includes taxes & fees
29 Jun - 30 Jun
King bed Crystal Lake Mchenry Cary Cozy
Interior

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

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (52 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is €295
includes taxes & fees
13 Jul - 14 Jul
The Tailor House
Interior

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
8.4 out of 10, Very good, (8 reviews)
"Cute and cozy little house. Convenient location. I would stay there again if the need ever comes up again. "
United States
holly g.
The price is €268
includes taxes & fees
30 Jun - 1 Jul
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
Exterior

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 Main Event Game House on the Huntley Square!
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
9.8 out of 10, Exceptional, (8 reviews)
"Super comfy for families and the nicest host. "
United States
Anonymous traveller
The price is €495
includes taxes & fees
28 Jun - 29 Jun
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Fridge, microwave, oven, stovetop

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
The price is €237
includes taxes & fees
6 Jul - 7 Jul
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Paper towels, dining tables

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
Private kitchen

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare

3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Addison
The price is €465
includes taxes & fees
30 Jun - 1 Jul
3BR Sleeps 12, 9 Parking Spots, 20 Min to O’Hare
Paper towels, dining tables

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
10.0 out of 10, Exceptional, (1 review)
"Perfect house for our family trip. Plenty of space for everyone. "
United States
Kristine T.
The price is €524
includes taxes & fees
29 Jun - 30 Jun
PROMO 10% WEEKLY AND 15% MONTHLY! Spacious & Quaint Home Game Room LOTS of Beds!
TV

Relaxing Lake Zurich 3BR + Patio | LCP Collection

Relaxing Lake Zurich 3BR + Patio | LCP Collection
Lake Zurich
8.8 out of 10, Excellent, (6 reviews)
"This was by far the cleanest VRBO we have rented. The location was perfect for our visit. The fully fenced yard was great for our dogs. The host promptly responded to questions I had prior to and during our stay. "
United States
diana w.
The price is €504
includes taxes & fees
21 Jul - 22 Jul
Relaxing Lake Zurich 3BR + Patio | LCP Collection
Dining

Stylish Escape/Game Room/4 Brs

Stylish Escape/Game Room/4 Brs
Arlington Heights
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful modern home with a super fun game room in the basement! Generously stocked with coffee and other supplies needed for a comfortable stay. Close to a vibrant downtown area and OHare airport. Excellent communication with the owner too. We had a wonderful family trip and highly recommend this awesome Vrbo."
United States
Donna J.
The price is €854
includes taxes & fees
13 Jul - 14 Jul
Stylish Escape/Game Room/4 Brs
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.8 out of 10, Excellent, (6 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is €699
includes taxes & fees
9 Jul - 10 Jul
4BR Near Woodfield Mall & Metra | LCP Collection
Exterior

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard
Schaumburg
9.6 out of 10, Exceptional, (35 reviews)
"This is our second stay at the property. The place is clean, comfortable, and in a good location. I recommend it for families of six or fewer."
United States
David G.
The price is €550
includes taxes & fees
9 Jul - 10 Jul
Game room+ New Bath! Near Chicago and O’Hare +Fenced yard
Fridge, microwave, oven, stovetop

Bliss in Batavia near the Fox River

Bliss in Batavia near the Fox River
Batavia
9.8 out of 10, Exceptional, (31 reviews)
"Cute house, great yard and neighborhood, and host was very responsive."
United States
Shannon V.
The price is €701
includes taxes & fees
20 Jul - 21 Jul
Bliss in Batavia near the Fox River
Interior

Modern Suburban Oasis- 14 guest House. Family Friendly!

Modern Suburban Oasis- 14 guest House. Family Friendly!
Elgin
10.0 out of 10, Exceptional, (1 review)
The price is €853
includes taxes & fees
1 Jul - 2 Jul
Modern Suburban Oasis- 14 guest House. Family Friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sleepy Hollow Hotel Reviews

Country Inn & Suites by Radisson, Schaumburg, IL

Country Inn & Suites by Radisson, Schaumburg, IL

10/10 Excellent
"Front desk was very busy. The young lady handled herself very well. My only negative is she is so soft spoken it is very hard to hear her. Even my 14 year old commented on the fact he appreciated how helpful she was when he went down later, he just wished he could hear what she’s saying better and I had not even mentioned my thoughts. He too said soft spoken. She did excellent, was polite, knowledgeable and helpful, she is just quiet."
Lisa 1-night trip
Posted 9 hours ago
Country Inn & Suites by Radisson, Schaumburg, IL

Find out more about Sleepy Hollow

Sleepy Hollow Holiday Homes information

Number of reviews
279
Accommodation
198 Holiday Homes
Lowest Price
€213
Highest Price
€854

Explore a world of travel with Expedia