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

Sleepy Hollow Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (190 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is HK$1,187
HK$1,365 total
includes taxes & fees
12 Oct - 13 Oct
Stamford Suites
A shower with a glass door, a towel rack, a mirror, and a shower curtain.

2. Home & Away Hotel-Style

Home & Away Hotel-Style
2.0 star property
Bronx
The price is HK$2,354
HK$2,729 total
includes taxes & fees
27 Oct - 28 Oct
Home & Away Hotel-Style
A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

3. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is HK$2,142
HK$6,396 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.

4. 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, (2 reviews)
"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
The price is HK$3,178
HK$4,945 total
includes taxes & fees
12 Oct - 13 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.

5. 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 HK$2,465
HK$4,005 total
includes taxes & fees
12 Oct - 13 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.

6. 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
The price is HK$3,178
HK$4,725 total
includes taxes & fees
12 Oct - 13 Oct
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.

7. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.4 out of 10, (6 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is HK$2,218
HK$3,651 total
includes taxes & fees
12 Oct - 13 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.

8. 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 HK$2,536
HK$4,006 total
includes taxes & fees
12 Oct - 13 Oct
Luxury 1BR located in Prime Yonkers Area
A breakfast buffet with pastries, fruits, and a coffee station.

9. 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 HK$7,063
HK$9,036 total
includes taxes & fees
12 Oct - 13 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.

10. 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 HK$3,885
HK$5,612 total
includes taxes & fees
13 Oct - 14 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.

11. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is HK$6,710
HK$8,676 total
includes taxes & fees
12 Oct - 13 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.

12. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is HK$4,461
HK$8,888 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.

13. 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 HK$2,582
HK$3,963 total
includes taxes & fees
12 Oct - 13 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.

14. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is HK$6,710
HK$8,642 total
includes taxes & fees
13 Oct - 14 Oct
Prime Luxe 3-BR NYC - Free Parking
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

15. 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 HK$1,406
HK$2,777 total
includes taxes & fees
12 Oct - 13 Oct
Elegant Hideaway with Free Parking
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

16. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is HK$2,841
HK$4,348 total
includes taxes & fees
12 Oct - 13 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.

17. 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 HK$2,465
HK$3,927 total
includes taxes & fees
12 Oct - 13 Oct
Luxe 1BR Oasis - Prime NY Stay
A modern interior with a glass wall, seating area, and a view of the city.

18. The Arches Suites

The Arches Suites
3.5 star property
Bronx
The price is HK$901
HK$1,846 total
includes taxes & fees
2 Nov - 3 Nov
The Arches Suites
A modern living room with a sofa, armchairs, and a glass coffee table.

19. 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 HK$4,591
HK$6,305 total
includes taxes & fees
12 Oct - 13 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.

20. 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 HK$3,178
HK$4,725 total
includes taxes & fees
14 Oct - 15 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.
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Top Sleepy Hollow Hotel Reviews

Hilltop Inn & Suites

Hilltop Inn & Suites

10/10 Excellent
"All good"
Rachel 2-night trip
Posted 10 hours ago
Hilltop Inn & Suites

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.