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

Sleepy Hollow Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Sleepy Hollow vacation rentals

A garden with a stone wall, a wooden fence, and a gravel path.

1. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
$194 nightly
The price is $216
Sep 28 - Sep 29
Total with taxes and fees
Piermont Oasis
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

2. 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
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
$115 nightly
The price is $135
Aug 31 - Sep 1
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

3. 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, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
$298 nightly
The price is $341
Sep 2 - Sep 3
Total with taxes and fees
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

4. 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
$376 nightly
The price is $430
Aug 30 - Aug 31
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
A stone staircase leading up to a house, surrounded by greenery and a blue tarp.

5. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
$313 nightly
The price is $358
Sep 28 - Sep 29
Total with taxes and fees
Garden Loft with Patios & Green Space · Westchester Retreat
A room with two beds, white curtains, a ceiling light, and a window with a view.

6. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
$460 nightly
The price is $526
Aug 30 - Aug 31
Total with taxes and fees
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
An outdoor patio with a fire pit, green chairs, and a table.

7. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (9 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
$317 nightly
The price is $363
Sep 7 - Sep 8
Total with taxes and fees
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

8. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
$350 nightly
The price is $400
Aug 30 - Aug 31
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

9. Charming 2-bedroom Apartment with AC in Yonkers

Charming 2-bedroom Apartment with AC in Yonkers
Bryn Mawr
$362 nightly
The price is $426
Aug 30 - Aug 31
Total with taxes and fees
Charming 2-bedroom Apartment with AC in Yonkers
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

10. '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, (7 reviews)
"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.
$391 nightly
The price is $447
Sep 15 - Sep 16
Total with taxes and fees
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

11. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$357 nightly
The price is $397
Aug 30 - Aug 31
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking
A wooden staircase leading to a gazebo in a forested area with a metal railing.

12. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very Good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
$202 nightly
The price is $229
Sep 12 - Sep 13
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

13. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
$356 nightly
The price is $398
Aug 30 - Aug 31
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC
A modern living room with a sofa, a coffee table, and a bar stool.

14. 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.
$278 nightly
The price is $315
Sep 5 - Sep 6
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

15. 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
$378 nightly
The price is $423
Sep 1 - Sep 2
Total with taxes and fees
Modern Luxury Home w GameRoom & Parking
A wooden cabin with large windows, a wooden bench, and a view of the forest.

16. Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
$224 nightly
The price is $227
Aug 31 - Sep 1
Total with taxes and fees
Harriman Outdoor Center - Mountain Laurel Cabin
A house with a view of a bridge and mountains.

17. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (141 reviews)
"We had a great stay!!"
United States
Jasmine
$284 nightly
The price is $335
Sep 1 - Sep 2
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

18. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"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
$365 nightly
The price is $408
Aug 30 - Aug 31
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC
A compact kitchen with a refrigerator, a coffee maker, a sink, and a microwave.

19. The Subterranean Haven

The Subterranean Haven
North Side
8.8 out of 10, Excellent, (10 reviews)
"Great space but anlittle amall, the floor dips a few spots and the space is pretty tight, but perfect for a short term stay!"
United States
Hannah R.
$263 nightly
The price is $293
Aug 30 - Aug 31
Total with taxes and fees
The Subterranean Haven
A covered area with exercise equipment, chairs, and a view through large windows.

20. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
$262 nightly
The price is $292
Aug 31 - Sep 1
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss
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

Hampton Inn & Suites Teaneck Glenpointe

Hampton Inn & Suites Teaneck Glenpointe

10/10 Excellent
"Good hit breakfast in large area to eat. No waiting and helpful staff. Cruise left late and able to get paid late checkout. Highly recommend!"
Gordon 3-night trip
Posted 2 hours ago
Hampton Inn & Suites Teaneck Glenpointe

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 $174 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.

Explore a world of travel with Expedia

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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental outside of Sleepy Hollow is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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.