Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Sleepy Hollow vacation rentals

Interior

Charming 1-bedroom apartment in fabulous Gillette with AC

Charming 1-bedroom apartment in fabulous Gillette with AC
Gillette
$197 nightly
The price is $216
Feb 19 - Feb 20
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Gillette with AC
Pool

Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!

Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!
Gillette
10.0 out of 10, Exceptional, (2 reviews)
"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.
$582 nightly
The price is $640
Feb 19 - Feb 20
Total with taxes and fees
Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!
Fridge, microwave, oven, stovetop

3-bedroom townhome in charming Gillette with an unbeatable location.

3-bedroom townhome in charming Gillette with an unbeatable location.
Gillette
10.0 out of 10, Exceptional, (6 reviews)
"It was a really nice house with an awesome host and it has everything you need for a comfortable stay. "
United States
Bailey G.
$285 nightly
The price is $314
Feb 25 - Feb 26
Total with taxes and fees
3-bedroom townhome in charming Gillette with an unbeatable location.
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

Arbuckle Lodge

Arbuckle Lodge

10/10 Excellent
"The room was enormous with a large refrigerator and a Keurig coffee maker. Very comfortable bed."
Nancy 1-night trip
Posted 2 days ago
Arbuckle Lodge

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $216 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Sleepy Hollow?

Yes, we have vacation rentals close to well known local attractions in Sleepy Hollow, or you can select a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Sleepy Hollow?

A Farmhouse style lodge, Centrally Located & Family Friendly Unit!: This vacation home rental outside of Sleepy Hollow offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection 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 the sights like CAM-PLEX Multi-Event Facilities, Gillette Country Club, and Energy Capital Sports Complex. In the larger area, you’ll find Eagle Butte Coal Mine and AVA Community Art Center.

What’s a vacation rental in Sleepy Hollow like?

A vacation rental is a private property where you can stay for a couple of days or more in Sleepy Hollow. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.