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Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec
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Top Sleepy Hollow Hotel Reviews

Arbuckle Lodge

Arbuckle Lodge

10/10 Excellent
"Very clean, convenient, and could NOT beat that price!! I mean really for the price and what we got… Amazing in 2026 lol"
Bradley 1-night trip
Posted 11 hours ago
Arbuckle Lodge

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?

3-bedroom townhome in charming Gillette with an unbeatable location.: This vacation home rental outside of Sleepy Hollow offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Rockpile Museum. In the larger area, you’ll find Eagle Butte Coal Mine and Energy Capital Sports Complex.

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.