Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

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

10.0 out of 10, Exceptional, (3)
"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. "
The price is AU$358
includes taxes & fees
19 Oct - 20 Oct
3-bedroom townhome in charming Gillette with an unbeatable location.

Carter house : 100 year old house with a remodeled castle inspired feel.

9.8 out of 10, Exceptional, (30)
"Just what we were looking for."
Carter house : 100 year old house with a remodeled castle inspired feel.

Cozy home nestled in Gillette Wyoming. Near Camplex, hospital and downtown.

Cozy home nestled in Gillette Wyoming. Near Camplex, hospital and downtown.

A Farmhouse style lodge, Centrally Located & Family Friendly Unit!

10.0 out of 10, Exceptional, (26)
"Great location for our yearly trip and will be back again. "
A Farmhouse style lodge, Centrally Located & Family Friendly Unit!

Charming 1-bedroom apartment in fabulous Gillette with AC

The price is AU$319
includes taxes & fees
30 Sept - 1 Oct
Charming 1-bedroom apartment in fabulous Gillette with AC

The Ross House 1930's Craftsman Style House

9.8 out of 10, Exceptional, (28)
"Vintage treasure in the heart of Gillette. Comfortable beds & unique decor. Thank you for the kind hospitality!"
The Ross House 1930's Craftsman Style House

Camporee welcome

Camporee welcome

Western Carriage House Studio Suite- Western themed retreat- Full Kitchen & Bath

10.0 out of 10, Exceptional, (26)
"Great people, great place"
Western Carriage House Studio Suite- Western themed retreat- Full Kitchen & Bath

Lovely 3-bedroom house in Gillette with AC, WiFi Close to Cam-Plex

2.0 star property
Lovely 3-bedroom house in Gillette with AC, WiFi Close to Cam-Plex

Tremendous camper with A/C and full hookups. Close to the Camplex.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Host from another booking agent cancelled without notice. Host of The Tremendous Camper stepped in and saved the day! They were very responsive and saved our trip! "
Tremendous camper with A/C and full hookups. Close to the Camplex.

Cozy One Bedroom Cottage Getaway!

10.0 out of 10, Exceptional, (7)
"Charming older home professionally remodeled and decorated with antiques to keep its original history. It had everything we needed. The free passes to the museum across the street were such a great compliment to our trip and understanding the history of the area. We will be back for future stays in Gillette WY."
Cozy One Bedroom Cottage Getaway!

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

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."
The price is AU$1,066
includes taxes & fees
22 Oct - 23 Oct
Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!

Charming 4-bedroom house with WiFi and AC in enchanting Gillette

2.0 star property
Charming 4-bedroom house with WiFi and AC in enchanting Gillette

Camp on city lots in Gillette across the street from the Camplex.

1.0 star property
Camp on city lots in Gillette across the street from the Camplex.

Comfy cozy great location!

2.0 star property
Comfy cozy great 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

Find out more about Sleepy Hollow

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$319 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?

3-bedroom townhome in charming Gillette with an unbeatable location.: This holiday home rental outside of Sleepy Hollow offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Eagle Butte Coal Mine. In the wider area, you’ll find Bicentennial Park and Energy Capital Sports Complex.

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.