Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday rentals

10.0 out of 10, Exceptional, (5)
"What a beautiful home. We enjoyed this stay. The host was amazing and communicated so well with us. Provided coffee creamer and went about and beyond for us. "
United States
Megan H.
The price is AU$472
includes taxes & fees
11 Jan - 12 Jan 2026
3-bedroom townhome in charming Gillette with an unbeatable location.
The price is AU$281
includes taxes & fees
12 Jan - 13 Jan 2026
Charming 1-bedroom apartment in fabulous Gillette with AC
10.0 out of 10, Exceptional, (1)
"Great location for coming for a soccer tournament. Close enough (5-10 minutes) from everything needed - food, activities, and fun. Lots of space to spread out with a group and a cute yard to play in. Beds were really comfortable with nice bedding and a variety of pillows to fit anyone. A couple different seating areas to hang out and watch TV in the evening. We really enjoyed our stay! Sheri was super responsive and great to work with during our stay! I hope to stay here again when we return."
United States
Travis N.
The price is AU$964
includes taxes & fees
30 Dec - 31 Dec
Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!
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

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 favourite 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 depend 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 AU$281 per night. Entering your travel dates in the search wizard might find you 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

Can I find 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.

What are some of the best holiday rentals that Sleepy Hollow has to offer?

Carter house : 100 year old house with a remodeled castle inspired feel.: This holiday home rental outside of Sleepy Hollow is located in the city centre, and has a fireplace, a balcony and air conditioning to put you at ease 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. You can relax into your holiday with a garden and a library.

What’s there to see and do in Sleepy Hollow?

While exploring the area, visit the sights like CAM-PLEX Multi-Event Facilities, Bicentennial Park and Energy Capital Sports Complex. In the wider area, you’ll find Eagle Butte Coal Mine and Gillette Country Club.

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 WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.