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

Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Sleepy Hollow vacation rentals

Living area

1. 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 P13,903
P25,108 total
includes taxes & fees
Sep 1 - Sep 2
Luxury NYC Home Game Room Free Parking
Private kitchen

2. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is P11,066
P21,864 total
includes taxes & fees
Aug 21 - Aug 22
Elegant Hideaway with Free Parking
Dining

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, (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 P13,903
P26,544 total
includes taxes & fees
Aug 25 - Aug 26
Luxury NYC Home with Free Parking for 12
Dining

4. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is P13,903
P24,690 total
includes taxes & fees
Aug 25 - Aug 26
Prime Luxe 3-BR NYC - Free Parking
Living area

5. 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 P13,903
P25,378 total
includes taxes & fees
Aug 25 - Aug 26
Uscale 2BR Escape in the Heart of NYC
Living area

6. 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 P13,903
P24,760 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 3BR Luxe Escape near NYC
Living area

7. 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 P12,427
P23,109 total
includes taxes & fees
Aug 30 - Aug 31
Luxury 3 BR Near NYC with Easy Parking
Living area

8. 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 P12,512
P23,205 total
includes taxes & fees
Aug 24 - Aug 25
Luxury 3BR Family Home Game Room Parking
Room

9. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is P43,343
P77,562 total
includes taxes & fees
Sep 1 - Sep 2
Summer Pool Oasis Custom Bar Arcade Pool Table
Living area

10. 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 P6,729
P16,734 total
includes taxes & fees
Aug 21 - Aug 22
NY Luxury Apt Free Parking in PRIME Area
Living area

11. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
4.6 out of 10, (11 reviews)
"The property that I paid for 1st, they told me that the pipe busted after I paid the cleaning fee. I paid for a property to sleep 6 people so 1 person had to sleep on the floor & another person had to sleep on a broken futon couch. The bed I was sleeping on was broken & there was pee stains on sheet & blanket. I asked them for a discount because of the unexpected things my family went through & they stopped communicating with me until the next day. But do not get any property rental from these...
United States
Ronnie
The price is P15,447
P26,488 total
includes taxes & fees
Aug 23 - Aug 24
Modern Luxury Home w GameRoom & Parking
Living area

12. 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 P19,964
P31,541 total
includes taxes & fees
Sep 2 - Sep 3
Luxury 1BR located in Prime Yonkers Area
Living area

13. 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 P19,408
P30,919 total
includes taxes & fees
Aug 30 - Aug 31
Luxe 1BR Oasis - Prime NY Stay
Living area

14. 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 P13,903
P24,760 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 3BR Luxe Escape near NYC
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 P36,147
P49,646 total
includes taxes & fees
Aug 21 - Aug 22
Luxury 5 BR Home Free Parking
In-room dining

16. 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 P55,610
P71,142 total
includes taxes & fees
Sep 18 - Sep 19
3BR Prime Luxury NY - Free Parking
Living area

17. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is P52,830
P68,310 total
includes taxes & fees
Sep 2 - Sep 3
Two Wash
Exterior

18. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (162 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is P8,304
P9,550 total
includes taxes & fees
Aug 30 - Aug 31
Stamford Suites
Front of property - evening/night

19. Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (621 reviews)
"everything was fine"
United States
kato
The price is P6,843
P13,673 total
includes taxes & fees
Aug 23 - Aug 24
Global Luxury Suites at The Arches
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

Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Beautiful hotel. We were just staying the night as we traveled down south but it was so nice to come into this resort and feel like a little getaway. Room was very spacious, bathroom had everything you needed. Only downside is you pay for parking and the gates were up and didn’t even need to pay."
Dena 1-night trip
Posted 2 hours ago
Hyatt Regency Greenwich

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:

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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.

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.