Sleepy Hollow Vacation Rentals

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Our top choices for Sleepy Hollow vacation 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 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
$175 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
$230 nightly
The price is $263
Jan 26 - Jan 27
Total with taxes and fees
Elegant Hideaway with Free Parking

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, (15 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 19 - Jan 20
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
$287 nightly
The price is $322
Jan 19 - Jan 20
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
$232 nightly
The price is $260
Jan 19 - Jan 20
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
$228 nightly
The price is $258
Jan 23 - Jan 24
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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 reviews)
"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.
$389 nightly
The price is $395
Jan 19 - Jan 20
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
$243 nightly
The price is $272
Jan 25 - Jan 26
Total with taxes and fees
Luxe 1BR Oasis - Prime NY Stay

'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 reviews)
"Great stay!"
United States
Ann S.
$210 nightly
The price is $241
Jan 20 - Jan 21
Total with taxes and fees
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"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.
$351 nightly
The price is $354
Jan 19 - Jan 20
Total with taxes and fees
Local Artist Inspired | Walk to WestPoint + King Bed

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
$565 nightly
The price is $632
Jan 19 - Jan 20
Total with taxes and fees
Modern Comfort in the Heart of NYC

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 reviews)
"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.
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

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 review)
"The comfort and safety "
United States
Jolena
$220 nightly
The price is $237
Jan 19 - Jan 20
Total with taxes and fees
Spacious 2 bedroom apartment with 1 bathroom and private street entrance

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
$292 nightly
The price is $327
Jan 19 - Jan 20
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC

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 reviews)
"Great place great location"
United States
Daquan H.
$115 nightly
The price is $135
Jan 24 - Jan 25
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$265 nightly
The price is $297
Jan 19 - Jan 20
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
$329 nightly
The price is $377
Jan 19 - Jan 20
Total with taxes and fees
Luxury 3BR Home Game Room Free Parking

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (10 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$291 nightly
The price is $329
Jan 20 - Jan 21
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
$237 nightly
The price is $268
Jan 23 - Jan 24
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
$611 nightly
The price is $680
Jan 19 - Jan 20
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sleepy Hollow vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sleepy Hollow in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow vacation 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 vacation.

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 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.

What are some of the best vacation rentals in Sleepy Hollow?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental outside of Sleepy Hollow is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.