Search Sleepy Hollow Cottage 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

Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3
In one month
Aug 15 - Aug 17
In two months
Sep 12 - Sep 14

Browse Select Sleepy Hollow Cottages

Cozy 3 bedroom river cottage w/ indoor fireplace
Relax in this stylish living room with a large painting, console table, and comfortable armchairs.

Cozy 3 bedroom river cottage w/ indoor fireplace

9.8 out of 10, Exceptional, (16)
"This was our second time here and was great as the first time. Its the prefect location for our event at Canlan Sports. We've already booked for next year even!Thanks!"
Cozy 3 bedroom river cottage w/ indoor fireplace
Lakehouse Getaway
Enjoy a peaceful retreat in this single-story home surrounded by a lush lawn and trees, featuring a cozy front porch and a fire pit for relaxation.

Lakehouse Getaway

7.0 out of 10, Good, (2)
"I don’t want to seem overly critical or petty, but there wasn’t a table to sit at to eat. Granted it is a small lake cottage. "
Lakehouse Getaway
Home on Fox River: Modern Decor Style!
House (4 Bedrooms) | Interior

Home on Fox River: Modern Decor Style!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Overall I had a great stay ! "
Home on Fox River: Modern Decor Style!
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and gas stove.

Home w/ Office + Yard: 25 Mi to Downtown Chicago!

3.0 star property
Home w/ Office + Yard: 25 Mi to Downtown Chicago!
Little Fox Cottage - A Cozy Riverview Getaway
Enjoy a warm gathering spot with a functional outdoor fireplace and seating area.

Little Fox Cottage - A Cozy Riverview Getaway

10.0 out of 10, Exceptional, (15)
"The perfect place for a quiet winter weekend getaway. Relax and enjoy!"
Little Fox Cottage - A Cozy Riverview Getaway
Glendale Heights Home With Office and Backyard!
Relax in this stylish living space with a sofa, coffee table, and kitchenette featuring a microwave and oven.

Glendale Heights Home With Office and Backyard!

3.0 star property
6.0 out of 10, (1)
Glendale Heights Home With Office and Backyard!
Romantic Lake Cottage for Two. With Patio and Firepit.
Relax and socialize in a serene outdoor space with a sail-like water play structure, benches, and picnic tables.

Romantic Lake Cottage for Two. With Patio and Firepit.

10.0 out of 10, Exceptional, (2)
"Perfect location to relax and visit with family in the area."
Romantic Lake Cottage for Two. With Patio and Firepit.
Fox River Grove Home: Pets Welcome!
Cozy living room with a comfortable seating area, fireplace, and large window.

Fox River Grove Home: Pets Welcome!

3.0 star property
Fox River Grove Home: Pets Welcome!
Pet-friendly Bartlett Farmhouse w/ Deck!
Relax in this spacious living area with a large sofa, dining table, and loft area.

Pet-friendly Bartlett Farmhouse w/ Deck!

3.0 star property
Pet-friendly Bartlett Farmhouse w/ Deck!
Elegant Mount Prospect Home w/ Fire Pit!
Interior

Elegant Mount Prospect Home w/ Fire Pit!

3.0 star property
Elegant Mount Prospect Home w/ Fire Pit!
Day Trip to Chicago: Hoffman Estates Gem!
Interior

Day Trip to Chicago: Hoffman Estates Gem!

3.0 star property
Day Trip to Chicago: Hoffman Estates Gem!
Riverfront Retreat w/ Dock & Kayaks in Mchenry
Interior

Riverfront Retreat w/ Dock & Kayaks in Mchenry

3.0 star property
Riverfront Retreat w/ Dock & Kayaks in Mchenry
8 Mi to Nature Center: Streamwood Gem w/ Yard!
House (3 Bedrooms) | Interior

8 Mi to Nature Center: Streamwood Gem w/ Yard!

3.0 star property
8 Mi to Nature Center: Streamwood Gem w/ Yard!
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

Frequently asked questions

Why book your cottage in Sleepy Hollow with Expedia?
We think that vacations should be simple, so if you're looking for cottages in Sleepy Hollow at a competitive price, Expedia has got you covered. Keep the budget in check and choose a low-cost option far from the rush of the city, or book a 5-star cottage to pamper your favorite people.
How can I find cheap cottages in Sleepy Hollow?
A great way to track down cheap cottages in Sleepy Hollow is with Expedia's handy filter tool. Tailor your search results by budget, star rating and amenities to land awesome prices with only a few clicks.