Sleepy Hollow Vacation Rentals

  • 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
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Sleepy Hollow vacation rentals

Interior

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

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is P12,467
P27,143 total
includes taxes & fees
May 22 - May 23
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Living area

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is P58,631
P74,789 total
includes taxes & fees
May 22 - May 23
Two Wash
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is P58,631
P74,496 total
includes taxes & fees
May 23 - May 24
Prime Luxe 3-BR NYC - Free Parking
Living area

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 P24,824
P36,968 total
includes taxes & fees
May 22 - May 23
Luxury 3 BR Near NYC with Easy Parking
Living area

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (1 review)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
The price is P31,423
P44,351 total
includes taxes & fees
May 22 - May 23
3BR Prime Luxury near NYC w Arcade Room
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (118 reviews)
"I stay there because it's fully equipped to cook and parking is excellent."
United States
fatima
The price is P9,183
P10,561 total
includes taxes & fees
May 26 - May 27
Stamford Suites
5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is P53,826
P90,770 total
includes taxes & fees
May 28 - May 29
Summer Pool Oasis Custom Bar Arcade Pool Table
Living area

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 P33,944
P48,020 total
includes taxes & fees
May 23 - May 24
Luxury NYC Home Game Room Free Parking
Living area

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.6 out of 10, (8 reviews)
"Property bedding was dirty, carpet dirty, sofas were dirty. Not was listed in the pictures. Asked me for $900 deposit through Zelle. No respond. Expedia needs to investigate this company for false advertising. "
United States
Liliana
The price is P63,686
P80,444 total
includes taxes & fees
May 26 - May 27
Modern Luxury Home w GameRoom & Parking
Living area

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 P21,539
P33,910 total
includes taxes & fees
May 22 - May 23
Uscale 2BR Escape in the Heart of NYC
Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is P15,121
P38,371 total
includes taxes & fees
Jun 2 - Jun 3
Updated Home w/ Patio Half Mile to West Point
In-room dining

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 P61,717
P77,933 total
includes taxes & fees
May 23 - May 24
3BR Prime Luxury NY - Free Parking
Living area

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 P21,539
P33,293 total
includes taxes & fees
May 25 - May 26
Luxury 3BR Family Home Game Room Parking
Living area

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 P24,440
P36,538 total
includes taxes & fees
May 22 - May 23
Spacious 3BR Luxe Escape near NYC
Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is P6,721
P16,715 total
includes taxes & fees
May 27 - May 28
NY Luxury Apt Free Parking in PRIME Area
Living area

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 P9,258
P19,553 total
includes taxes & fees
May 27 - May 28
Luxury 1BR located in Prime Yonkers Area
Hypo-allergenic bedding, desk, laptop workspace, iron/ironing board

Global Luxury Suites White Plains

Global Luxury Suites White Plains
3.5 star property
White Plains
6.8 out of 10, (43 reviews)
"Please stay away from this horrible place!!! I have travelled all over the world but never dealt with such terrible company and their property. "
United States
Katerine
Global Luxury Suites White Plains
Exterior

Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (589 reviews)
"Very nice stay "
United States
Massaran
The price is P5,199
P11,777 total
includes taxes & fees
May 26 - May 27
Global Luxury Suites at The Arches
Living area

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 P40,116
P54,076 total
includes taxes & fees
May 22 - May 23
Luxury 5 BR Home Free Parking
Dining

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 P27,773
P41,979 total
includes taxes & fees
May 23 - May 24
Luxury NYC Home with Free Parking for 12
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

Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

8/10 Good
"Be careful with the low night rates. Don’t forget to think about the 15$/day parking fee + 14$/ person for breakfast (not sure if it is worth the money) A lot of traffic to get in/out as it is just next to the GWB entrance. +: The room is large and clean, rooms are renovated and beds comfortable."
Lucie 2-night trip
Posted less than an hour ago
Hyatt Place Fort Lee / George Washington Bridge

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 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 Legoland Discovery Center Westchester, 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.