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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Sleepy Hollow holiday rentals

Exterior

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (157 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is 3.683.469 ₫
4.235.989 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Stamford Suites
Luxury Apartment | Living area

2. NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is 2.846.210 ₫
7.078.462 ₫ total
includes taxes & fees
20 Aug - 21 Aug
NY Luxury Apt Free Parking in PRIME Area
Luxury Apartment | Living area

3. 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 9.461.415 ₫
14.479.220 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Luxury 3 BR Near NYC with Easy Parking
Luxury House | Living area

4. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is 22.346.280 ₫
28.894.164 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Two Wash
Luxury Apartment | Private kitchen

5. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is 4.680.958 ₫
9.248.111 ₫ total
includes taxes & fees
21 Aug - 22 Aug
Elegant Hideaway with Free Parking
Dining

6. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is 22.346.280 ₫
28.782.433 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Prime Luxe 3-BR NYC - Free Parking
Luxury Apartment | In-room dining

7. 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 23.522.400 ₫
30.092.337 ₫ total
includes taxes & fees
24 Aug - 25 Aug
3BR Prime Luxury NY - Free Parking
House | 5 bedrooms

8. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is 19.762.988 ₫
34.411.656 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Apartment (1 Bedroom) | Interior

9. 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 3.711.312 ₫
7.577.088 ₫ total
includes taxes & fees
23 Aug - 24 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Luxury House, Garden View | Living area

10. 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
The price is 7.388.386 ₫
12.160.021 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Luxury 3BR Family Home Game Room Parking
Luxury Apartment | Living area

11. 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 8.209.318 ₫
13.078.438 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Luxe 1BR Oasis - Prime NY Stay
Front of property – evening/night

12. Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (620 reviews)
"everything was fine"
United States
kato
The price is 2.582.760 ₫
5.424.487 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Global Luxury Suites at The Arches
Villa, Garden View | Living area

13. 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 12.937.320 ₫
18.691.324 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Luxury NYC Home Game Room Free Parking
House | Living area

14. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
4.8 out of 10, (10 reviews)
"Don’t stay here. Not as listed. "
United States
Kenyon
The price is 31.729.104 ₫
39.391.198 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Modern Luxury Home w GameRoom & Parking
Luxury Villa, Patio | Living area

15. 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 15.289.560 ₫
20.999.459 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Luxury 5 BR Home Free Parking
Luxury Villa, Garden View | Dining

16. 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
The price is 10.585.080 ₫
16.467.476 ₫ total
includes taxes & fees
13 Aug - 14 Aug
Luxury NYC Home with Free Parking for 12
Luxury Duplex | Living area

17. 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
The price is 8.209.318 ₫
13.339.800 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Uscale 2BR Escape in the Heart of NYC
Luxury Apartment | Living area

18. 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 8.444.542 ₫
13.341.595 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Luxury 1BR located in Prime Yonkers Area
Luxury House | Living area

19. 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
The price is 10.585.080 ₫
15.736.322 ₫ total
includes taxes & fees
19 Aug - 20 Aug
Spacious 3BR Luxe Escape near NYC
Luxury House | Living area

20. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (1 review)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
The price is 10.585.080 ₫
15.736.322 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Spacious 3BR Luxe Escape near 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

DoubleTree by Hilton Fort Lee - George Washington Bridge

DoubleTree by Hilton Fort Lee - George Washington Bridge

10/10 Excellent
"Excelente opcion para hospedaje, camas muy comodas, todo en perfecto estado y una limpieza impecable"
Rafael 3-night trip
Posted 1 hour ago
DoubleTree by Hilton Fort Lee - George Washington Bridge

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.

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.