Sleepy Hollow Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 23 - Jul 24
Tomorrow
Jul 24 - Jul 25
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Vacation Rentals in Sleepy Hollow

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

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

9.8 out of 10, Exceptional, (30)
"Great place Awesome!"
Carter house : 100 year old house with a remodeled castle inspired feel.
WEEKLY/MONTHLY/DAILY/Free Breakfast/Clean Rooms
1 bedroom, desk, iron/ironing board, travel crib

WEEKLY/MONTHLY/DAILY/Free Breakfast/Clean Rooms

2.8 out of 10, (3)
"Never again "
The price is ￥15,833
￥23,867 total
includes taxes & fees
Aug 23 - Aug 24
WEEKLY/MONTHLY/DAILY/Free Breakfast/Clean Rooms
A Farmhouse style lodge, Centrally Located & Family Friendly Unit!
Smart TV, fireplace

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

10.0 out of 10, Exceptional, (23)
"This place was so cute inside. We loved it. I would stay again. Thank you "
A Farmhouse style lodge, Centrally Located & Family Friendly Unit!
Cozy One Bedroom Cottage Getaway!
Balcony

Cozy One Bedroom Cottage Getaway!

10.0 out of 10, Exceptional, (7)
"The cottage was perfect for us!! It is a very cute home. "
Cozy One Bedroom Cottage Getaway!
The Ross House 1930's Craftsman Style House
Property grounds

The Ross House 1930's Craftsman Style House

10.0 out of 10, Exceptional, (26)
"Wonderful house, great central location, plenty of room, clean, great host. "
The Ross House 1930's Craftsman Style House
Western Carriage House Studio Suite- Western themed retreat- Full Kitchen & Bath
Property grounds

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

10.0 out of 10, Exceptional, (25)
"Beautiful property. Nice, quiet clean property. Love the decor! "
Western Carriage House Studio Suite- Western themed retreat- Full Kitchen & Bath
Tremendous camper with A/C and full hookups. Close to the Camplex.
Dining

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.
Camporee welcome
Interior

Camporee welcome

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

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."
Cozy 5bdrm Haven in the Heart of Gillette 5 Min from Downtown- FREE Pool Passes!
Lovely 3-bedroom house in Gillette with AC, WiFi Close to Cam-Plex
Terrace/patio

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

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!
Terrace/patio

Comfy cozy great location!

2.0 star property
Comfy cozy great location!
Charming 4-bedroom house with WiFi and AC in enchanting Gillette
Private kitchen

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
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
Sign in
Sign up, it's free

Top Sleepy Hollow Hotel Reviews

Comfort Inn & Suites Gillette near Campbell Medical Center

Comfort Inn & Suites Gillette near Campbell Medical Center

10/10 Excellent
"Best hotel and amenities of our entire trip. A great hotel for a small town."
Joy 1-night trip
Posted 2 days ago
Comfort Inn & Suites Gillette near Campbell Medical Center

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?

Carter house : 100 year old house with a remodeled castle inspired feel.: This vacation home rental outside of Sleepy Hollow is located in the city center 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 you can cook with friends or family. You can relax into your vacation 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 Eagle Butte Coal Mine. In the larger area, you’ll find Energy Capital Sports Complex and Gillette Country Club.

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.