Search Villas in Sleepy Hollow

    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

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Villas in Sleepy Hollow

Spacious Retreat w/ Pool, Hot Tub & Game Room
Stunning two-story residence with a central entrance, arched window, and charming front porch.

Spacious Retreat w/ Pool, Hot Tub & Game Room

Spacious Retreat w/ Pool, Hot Tub & Game Room
Charming Getaway Villa
Relax by the pool surrounded by lush greenery and enjoy refreshing drinks at the poolside table.

Charming Getaway Villa

2.0 star property
Charming Getaway Villa
Luxury 5-Bdrm Getaway Near West Point
Surrounded by lush greenery, this outdoor fireplace offers a serene setting.

Luxury 5-Bdrm Getaway Near West Point

3.0 star property
10.0 out of 10, Exceptional, (3)
"Stayed for 3 nights with friends and family had an absolute blast! Amazing house! 100% would book this house again. I highly recommend this house. Very clean and very comfortable. If you had any questions owner would get back to you very quickly. Overall 10/10 stay!"
Luxury 5-Bdrm Getaway Near West Point
Hudson Valley Estate on 4 Acres w/ Private Pool!
Stunning two-story building with a red-tiled roof, surrounded by lush greenery and mature trees.

Hudson Valley Estate on 4 Acres w/ Private Pool!

Hudson Valley Estate on 4 Acres w/ Private Pool!
Scenic Spring Home With Outdoor Dining Charm
Stunning two-story home with a central entrance and two wings, set amidst a serene and environment.

Scenic Spring Home With Outdoor Dining Charm

2.0 star property
Scenic Spring Home With Outdoor Dining Charm
Hudson Valley Estate on 4 Acres w/ Private Pool!
Stunning two-story house surrounded by lush greenery and trees, featuring a symmetrical facade with evenly spaced windows and a central entrance.

Hudson Valley Estate on 4 Acres w/ Private Pool!

3.0 star property
Hudson Valley Estate on 4 Acres w/ Private Pool!
Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York
Stairs lead up to a covered porch with columns and a balustrade.

Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York

Historic Castle 1876 13 Mins to Wing Foot cc border of GREENWICH and New York
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

Highbridge Hotel

Highbridge Hotel

10/10 Excellent
"The hotel was nice and clean. And very convenient for getting around."
Jeanette 5-night trip
Posted 6 hours ago
Highbridge Hotel