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Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday rentals

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
Cozy 1-bedroom retreat minutes from West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
The price is AU$424
includes taxes & fees
19 Dec - 20 Dec
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (9)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is AU$604
includes taxes & fees
19 Dec - 20 Dec
Local Artist Inspired | Walk to WestPoint + King Bed

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is AU$444
includes taxes & fees
28 Dec - 29 Dec
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Greenwich
9.6 out of 10, Exceptional, (23)
"This was a great place! The host George and his wife were incredibly helpful and so nice, making the stay even better. I would absolutely recommend this spot to anyone and definitely plan to be back again!"
United States
Alexus C.
The price is AU$426
includes taxes & fees
20 Dec - 21 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Marvelous 1-bedroom with sofa bed 5 minutes from NYC

Marvelous 1-bedroom with sofa bed 5 minutes from NYC
2.0 star property
Palisades Park
Marvelous 1-bedroom with sofa bed 5 minutes from NYC

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is AU$557
includes taxes & fees
25 Dec - 26 Dec
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.2 out of 10, Very good, (18)
"Great place great location"
United States
Daquan H.
The price is AU$206
includes taxes & fees
21 Dec - 22 Dec
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is AU$373
includes taxes & fees
21 Dec - 22 Dec
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Spacious 2 bedroom apartment with 1 bathroom and private street entrance

Spacious 2 bedroom apartment with 1 bathroom and private street entrance
2.0 star property
Paterson
10.0 out of 10, Exceptional, (1)
"The comfort and safety "
United States
Jolena
The price is AU$418
includes taxes & fees
7 Jan - 8 Jan 2026
Spacious 2 bedroom apartment with 1 bathroom and private street entrance

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 AU$415
includes taxes & fees
28 Dec - 29 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AU$422
includes taxes & fees
21 Dec - 22 Dec
Fabulous 3bdrm Home w/parking!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is AU$465
includes taxes & fees
21 Dec - 22 Dec
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (9)
"Excellent property, very clean, nicely furnished. One of the best VRBOs we have rented. Owner was exceptionally good about communication and went out of his way to make sure stay went well. Will come again. "
United States
David S.
The price is AU$664
includes taxes & fees
2 Jan - 3 Jan 2026
Seabreeze at the beach west beach Stamford ct.

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is AU$487
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC

2 DEEP Discounted Apts by American Dream, Sleeps 8

2 DEEP Discounted Apts by American Dream, Sleeps 8
2.0 star property
Hasbrouck Heights
9.4 out of 10, Exceptional, (3)
"The apartment was nice and clean and a designated parking right at the door. The host was very helpful."
United States
Irma E.
The price is AU$539
includes taxes & fees
5 Jan - 6 Jan 2026
2 DEEP Discounted Apts by American Dream, Sleeps 8

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is AU$668
includes taxes & fees
13 Jan - 14 Jan 2026
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11)
"loved walking the city. pizza was good."
United States
michelle b.
The price is AU$408
includes taxes & fees
28 Dec - 29 Dec
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
United States
Molly s.
The price is AU$579
includes taxes & fees
5 Jan - 6 Jan 2026
Lovely 3BR Home with parking-Walk to WP Gate!

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is AU$1,026
includes taxes & fees
16 Jan - 17 Jan 2026
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.
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Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sleepy Hollow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sleepy Hollow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sleepy Hollow holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside Sleepy Hollow is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

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 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.