A wooden structure with a bridge over a body of water, surrounded by trees.

Sleepy Hollow Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Sleepy Hollow vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (193 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$164 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
Stamford Suites
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

2. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
$732 nightly
The price is $815
Oct 21 - Oct 22
Total with taxes and fees
Snow Days & City Escapes: Spacious Ossining Home
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

3. 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, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
$611 nightly
The price is $680
Oct 16 - Oct 17
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

4. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"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
$491 nightly
The price is $549
Oct 17 - Oct 18
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

5. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
Spacious 3BR Luxe Escape near NYC
A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

6. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.0 out of 10, (7 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
$482 nightly
The price is $539
Oct 16 - Oct 17
Total with taxes and fees
Luxury 3BR Family Home Game Room Parking
A modern kitchen with white cabinets, a central island with stools, a stone accent wall, a flat-screen TV, and a beige sofa with teal cushions.

7. 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
$492 nightly
The price is $551
Oct 16 - Oct 17
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area
A breakfast buffet with pastries, fruits, and a coffee station.

8. 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
$1,134 nightly
The price is $1,263
Oct 16 - Oct 17
Total with taxes and fees
3BR Prime Luxury NY - Free Parking
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

9. 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
$680 nightly
The price is $778
Oct 16 - Oct 17
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

10. Two Wash

Two Wash
2.0 star property
Bryn Mawr
$1,083 nightly
The price is $1,212
Oct 16 - Oct 17
Total with taxes and fees
Two Wash
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

11. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,008 nightly
The price is $1,123
Nov 3 - Nov 4
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

12. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
$439 nightly
The price is $505
Oct 18 - Oct 19
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

13. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$1,084 nightly
The price is $1,207
Oct 16 - Oct 17
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

14. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
$329 nightly
The price is $377
Oct 16 - Oct 17
Total with taxes and fees
Elegant Hideaway with Free Parking
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

15. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
"This is a scam and at the same time others guest’s was there for same booking but we can’t get any feed the property support and we returned from the property and kids suffered a lot!!!"
United States
Md Asadul
$535 nightly
The price is $599
Oct 16 - Oct 17
Total with taxes and fees
Luxury 3 BR Near NYC with Easy Parking
A modern living room with a stone wall, a flat-screen TV, a white sofa, and a kitchen area with a bar counter and chairs.

16. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
$482 nightly
The price is $539
Oct 16 - Oct 17
Total with taxes and fees
Luxe 1BR Oasis - Prime NY Stay
A modern interior with a wooden ceiling, large glass doors leading to a living area with a sofa, chairs, and a dining table.

17. The Arches Suites

The Arches Suites
2.0 star property
Bronx
$189 nightly
The price is $220
Nov 10 - Nov 11
Total with taxes and fees
The Arches Suites
A modern living room with a sofa, armchairs, and a glass coffee table.

18. 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)
$783 nightly
The price is $876
Oct 16 - Oct 17
Total with taxes and fees
Luxury 5 BR Home Free Parking
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

19. Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
3.2 out of 10, (5 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
$583 nightly
The price is $652
Oct 16 - Oct 17
Total with taxes and fees
Modern Comfort in the Heart of NYC
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

Marriott Saddle Brook

Marriott Saddle Brook

8/10 Good
"I Like turtles"
Ryan 3-night trip
Posted 17 hours ago
Marriott Saddle Brook

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 $189 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.

Explore a world of travel with Expedia

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 of Sleepy Hollow is situated near the airport and has a rooftop terrace and free 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.