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

Search Holiday Rentals in Sleepy Hollow

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Sleepy Hollow holiday 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, (192 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ฿4,995
฿5,744 total
includes taxes & fees
15 Oct - 16 Oct
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
The price is ฿9,164
฿27,356 total
includes taxes & fees
21 Oct - 22 Oct
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
The price is ฿13,595
฿21,150 total
includes taxes & fees
15 Oct - 16 Oct
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
The price is ฿10,543
฿17,133 total
includes taxes & fees
17 Oct - 18 Oct
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
The price is ฿9,489
฿15,617 total
includes taxes & fees
15 Oct - 16 Oct
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
The price is ฿10,845
฿17,135 total
includes taxes & fees
23 Oct - 24 Oct
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
The price is ฿30,210
฿38,648 total
includes taxes & fees
15 Oct - 16 Oct
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
The price is ฿16,616
฿24,006 total
includes taxes & fees
15 Oct - 16 Oct
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
The price is ฿28,700
฿37,109 total
includes taxes & fees
21 Oct - 22 Oct
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
The price is ฿17,207
฿35,075 total
includes taxes & fees
3 Nov - 4 Nov
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
The price is ฿11,044
฿16,950 total
includes taxes & fees
18 Oct - 19 Oct
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
The price is ฿28,700
฿36,966 total
includes taxes & fees
18 Oct - 19 Oct
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)
The price is ฿6,012
฿11,878 total
includes taxes & fees
18 Oct - 19 Oct
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
The price is ฿12,151
฿18,596 total
includes taxes & fees
15 Oct - 16 Oct
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
The price is ฿10,543
฿16,797 total
includes taxes & fees
15 Oct - 16 Oct
Luxe 1BR Oasis - Prime NY Stay
A modern gym with cardio machines, weight stations, and a mirrored wall.

17. The Arches Suites

The Arches Suites
2.0 star property
Bronx
The price is ฿3,852
฿7,894 total
includes taxes & fees
10 Nov - 11 Nov
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)
The price is ฿19,637
฿26,970 total
includes taxes & fees
15 Oct - 16 Oct
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
3.6 out of 10, (4 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
The price is ฿13,595
฿20,210 total
includes taxes & fees
15 Oct - 16 Oct
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.
View all properties
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

Radio Hotel

Radio Hotel

8/10 Good
"The size of the room and the cleanliness but the customer service was excellent. I also enjoyed the voucher. Close to the metro station."
Ana 1-night trip
Posted 4 hours ago
Radio Hotel

Find out more about Sleepy Hollow

Search for holiday rentals in Sleepy Hollow on Expedia! You can easily find your home rentals, villas, holiday apartments in Sleepy Hollow using one of the methods below:

  • View our selection of featured holiday rentals in Sleepy Hollow
  • Use the map to find apartments and other holiday homes in the Sleepy Hollow neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sleepy Hollow while they last

Look no further and take a look at our great range of rental properties in Sleepy Hollow!

Frequently asked questions

Can I find a holiday rental in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Sleepy Hollow has to offer?

Modern Luxury Home w GameRoom & Parking: This holiday 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 that you can cook with friends or family.

How many holiday rentals are there in Sleepy Hollow?

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

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 holiday rentals like in Sleepy Hollow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sleepy Hollow. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.