Default HTG hotel image

Sleepy Hollow Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sleepy Hollow holiday rentals

1. 124 Lofts #4 - Downtown Dundee - Walk to Dining

124 Lofts #4 - Downtown Dundee - Walk to Dining
West Dundee
9.8 out of 10, Exceptional, (20 reviews)
"Wonderful loft, highly recommend!"
United States
Bret V.
The price is NZ$423
includes taxes & fees
9 Nov - 10 Nov
124 Lofts #4 - Downtown Dundee - Walk to Dining

2. Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (20 reviews)
"We really enjoyed our stay. We have so much family in IL - it was nice to have dinner with a few of them right at our 'home' away from home and not eat out every night. Make sure everyone knows there are a LOT of stairs - so that everyone from the toddler to the 94 yr old that visits knows they are going to 'climb'... :)"
United States
M/M P.
The price is NZ$465
includes taxes & fees
6 Dec - 7 Dec
Kildahl House - Boutique Farmhouse Suite #4

3. ✨ 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 NZ$588
includes taxes & fees
17 Nov - 18 Nov
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

4. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay at the Kildahl House! It is clean, cozy, charming. The location is perfect and accessible to to the river and downtown. I loved the connections Andy and Suzanne have made with local businesses to make your stay even more enjoyable!"
United States
Elise L.
The price is NZ$484
includes taxes & fees
12 Nov - 13 Nov
Kildahl House - Boutique Farmhouse Suite #1

5. 124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is NZ$394
includes taxes & fees
15 Nov - 16 Nov
124 Lofts #1 - Downtown Dundee - Walk to Dining

6. 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, (25 reviews)
"This was a great house with a beautiful property!"
United States
Malcolm S.
The price is NZ$831
includes taxes & fees
17 Nov - 18 Nov
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago

7. 124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (28 reviews)
"Lovely stay! Great location!"
United States
David K.
The price is NZ$421
includes taxes & fees
9 Nov - 10 Nov
124 Lofts #3 - Downtown Dundee - Walk to Dining

8. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (19 reviews)
"I would stay here again in a heartbeat!"
United States
Rebecca R.
The price is NZ$467
includes taxes & fees
6 Dec - 7 Dec
Kildahl House - Boutique Farmhouse Suite #2

9. 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 NZ$435
includes taxes & fees
9 Nov - 10 Nov
The Main Event Game House on the Huntley Square!

10. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
9.8 out of 10, Exceptional, (20 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is NZ$319
includes taxes & fees
8 Nov - 9 Nov
Little Fox Cottage - A Cozy Riverview Getaway

11. 124 Lofts #2 - Downtown Dundee - Walk to Dining

124 Lofts #2 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (24 reviews)
"It was an absolute beautiful place and I’d stay again if I’m ever in the area."
United States
steve m.
The price is NZ$441
includes taxes & fees
17 Nov - 18 Nov
124 Lofts #2 - Downtown Dundee - Walk to Dining

12. Kildahl House - Boutique Farmhouse Suite #3

Kildahl House - Boutique Farmhouse Suite #3
West Dundee
10.0 out of 10, Exceptional, (23 reviews)
"Excellent place will definitely be back, the owners seem like great people as well"
United States
George N.
The price is NZ$478
includes taxes & fees
19 Nov - 20 Nov
Kildahl House - Boutique Farmhouse Suite #3

13. Spacious Creekside Suite Near Chicago

Spacious Creekside Suite Near Chicago
barrington hill
The price is NZ$390
includes taxes & fees
29 Nov - 30 Nov
Spacious Creekside Suite Near Chicago

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

Perfect Family Getaway: Spacious 5BR Home in Barrington
Barrington
The price is NZ$6,063
includes taxes & fees
9 Nov - 10 Nov
Perfect Family Getaway: Spacious 5BR Home in Barrington

15. 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 NZ$505
includes taxes & fees
7 Nov - 8 Nov
Spacious 3 Bedroom

16. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (52 reviews)
"Incredible host and property."
United States
John V.
The price is NZ$430
includes taxes & fees
17 Nov - 18 Nov
Riverfront rental

17. 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 NZ$613
includes taxes & fees
9 Nov - 10 Nov
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

18. 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 NZ$1,611
includes taxes & fees
9 Nov - 10 Nov
Modern Suburban Oasis- 14 guest House. Family Friendly!

19. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is NZ$851
includes taxes & fees
10 Nov - 11 Nov
King bed Crystal Lake Mchenry Cary Cozy

20. Spacious Getaway Near O’Hare

Spacious Getaway Near O’Hare
Schaumburg
9.6 out of 10, Exceptional, (37 reviews)
"Host was amazing, house was clean and easy to access! "
United States
Central A.
The price is NZ$743
includes taxes & fees
8 Nov - 9 Nov
Spacious Getaway Near O’Hare
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sleepy Hollow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sleepy Hollow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sleepy Hollow holiday rentals we have selected for you start as low as NZ$319 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Spacious open concept home w/ game room + firepit: This holiday home rental outside of Sleepy Hollow offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and kitchenware, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Elgin Sports Complex. In the wider area, you’ll find Randall Oaks Golf Club and Hemmens Cultural Center.

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.