Sleepy Hollow Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sleepy Hollow vacation rentals

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (113 reviews)
"Was very nice & clean. "
United States
Kelly
$130 nightly
The price is $150
May 10 - May 11
Total with taxes and fees
Stamford Suites

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
$495 nightly
The price is $554
May 17 - May 18
Total with taxes and fees
Luxury 3 BR Near NYC with Easy Parking

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
$505 nightly
The price is $622
Jun 2 - Jun 3
Total with taxes and fees
Updated Home w/ Patio Half Mile to West Point

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1 review)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$642 nightly
The price is $719
May 9 - May 10
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
$667 nightly
The price is $762
May 21 - May 22
Total with taxes and fees
Luxury NYC Home Game Room Free Parking

Two Wash

Two Wash
2.0 star property
Bryn Mawr
$988 nightly
The price is $1,106
May 31 - Jun 1
Total with taxes and fees
Two Wash

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
$242 nightly
The price is $271
May 31 - Jun 1
Total with taxes and fees
NY Luxury Apt Free Parking in PRIME Area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
$538 nightly
The price is $602
May 11 - May 12
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
$1,514 nightly
The price is $1,687
May 13 - May 14
Total with taxes and fees
Westchester Summer Pool Pet Friendly Events Games

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
$472 nightly
The price is $539
May 21 - May 22
Total with taxes and fees
Luxury 3BR Home Game Room Free Parking

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$1,060 nightly
The price is $1,181
May 21 - May 22
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very Good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
$456 nightly
The price is $510
May 17 - May 18
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
$290 nightly
The price is $334
May 13 - May 14
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
$1,109 nightly
The price is $1,235
May 21 - May 22
Total with taxes and fees
3BR Prime Luxury NY - Free Parking

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
$447 nightly
The price is $500
May 11 - May 12
Total with taxes and fees
Luxury 3BR Family Home Game Room Parking

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
$279 nightly
The price is $313
May 21 - May 22
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area

Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (588 reviews)
"Very nice stay "
United States
Massaran
$184 nightly
The price is $215
May 10 - May 11
Total with taxes and fees
Global Luxury Suites at The Arches

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.6 out of 10, (8 reviews)
"Property bedding was dirty, carpet dirty, sofas were dirty. Not was listed in the pictures. Asked me for $900 deposit through Zelle. No respond. Expedia needs to investigate this company for false advertising. "
United States
Liliana
$1,131 nightly
The price is $1,265
May 13 - May 14
Total with taxes and fees
Modern Luxury Home w GameRoom & Parking

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
$718 nightly
The price is $803
May 31 - Jun 1
Total with taxes and fees
Luxury 5 BR Home Free Parking

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
$599 nightly
The price is $668
May 21 - May 22
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
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

Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation 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 vacation.

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 a vacation rental in Sleepy Hollow?

Yes, there are vacation rentals near the most popular sights in Sleepy Hollow, or you can go with a more secluded option if you're looking for relaxation. Sleepy Hollow is known for its churches and local tours. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals in Sleepy Hollow?

Modern Luxury Home w GameRoom & Parking: This vacation home rental outside Sleepy Hollow is situated near the airport and has a rooftop terrace and WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Sleepy Hollow?

Choose from 3 Expedia vacation rentals in Sleepy Hollow for a memorable vacation.

What can I see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Rockland Bakery, or get outside and enjoy nature at Rockefeller State Park Preserve. Other places in town to visit include Philipsburg Manor and Old Dutch Church of Sleepy Hollow.

What are vacation rentals like in Sleepy Hollow?

Vacation rentals are private accommodations you can reserve for several days or longer in Sleepy Hollow. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family trip or a small group gathering.