Sleepy Hollow Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Sleepy Hollow vacation rentals

Property grounds

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, (138 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is ￥31,535
￥51,926 total
includes taxes & fees
Jun 1 - Jun 2
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

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
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥28,525
￥57,491 total
includes taxes & fees
Jun 1 - Jun 2
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

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

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥27,235
￥51,388 total
includes taxes & fees
Jun 3 - Jun 4
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥20,235
￥36,796 total
includes taxes & fees
Jun 3 - Jun 4
Cozy 1-bedroom retreat minutes from West Point!
Fridge, oven, stovetop, coffee/tea maker

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, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is ￥18,316
￥48,875 total
includes taxes & fees
Jun 3 - Jun 4
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
TV, books, offices

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
8.8 out of 10, Excellent, (6 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
The price is ￥37,428
￥66,261 total
includes taxes & fees
Jun 17 - Jun 18
Bright&Comfy 2bed/1ba in quiet White Plains duplex
Terrace/patio

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.
The price is ￥15,051
￥21,476 total
includes taxes & fees
Jun 1 - Jun 2
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Dining

Gorgeous, 2- bedroom apartment walking distance to GWB!

Gorgeous, 2- bedroom apartment walking distance to GWB!
Fort Lee
10.0 out of 10, Exceptional, (12 reviews)
"Yes nice place"
United States
Scott b.
The price is ￥31,535
￥59,492 total
includes taxes & fees
Jun 3 - Jun 4
Gorgeous, 2- bedroom apartment walking distance to GWB!
Offices

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)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥22,935
￥50,266 total
includes taxes & fees
Jun 12 - Jun 13
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Smart TV

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥22,935
￥66,671 total
includes taxes & fees
Jun 3 - Jun 4
Modern Luxe 1BR Apt in Downtown Stamford
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is ￥35,039
￥66,672 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥19,112
￥33,526 total
includes taxes & fees
Jun 15 - Jun 16
Piermont Oasis
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is ￥32,826
￥68,689 total
includes taxes & fees
Jun 29 - Jun 30
Stamford Hideaway w/ Fire Pit
Dining

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, (91 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.
The price is ￥22,744
￥49,692 total
includes taxes & fees
Jun 1 - Jun 2
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is ￥35,836
￥66,855 total
includes taxes & fees
Jun 1 - Jun 2
Contemporary Cozy Cottage
Free toiletries, hair dryer, towels

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
Highland Falls
10.0 out of 10, Exceptional, (33 reviews)
"Great location, good communication, and wonderfully appointed."
United States
george l.
Updated Home w/ Patio Half Mile to West Point
Interior

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is ￥31,217
￥36,185 total
includes taxes & fees
Jun 4 - Jun 5
Harriman Outdoor Center - Mountain Laurel Cabin
Desk, free WiFi, bed sheets

'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.
The price is ￥25,977
￥50,841 total
includes taxes & fees
Jun 14 - Jun 15
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
2 bedrooms, WiFi

Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins

Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins
Paterson
10.0 out of 10, Exceptional, (1 review)
"The comfort and safety "
United States
Jolena
The price is ￥17,031
￥41,065 total
includes taxes & fees
Jun 8 - Jun 9
Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins
TV

The Classic Suite: 2BR close to NYC

The Classic Suite: 2BR close to NYC
Paterson
10.0 out of 10, Exceptional, (1 review)
"The property has everything we needed for a two night stay. Driving to NYC is approximately 40 mins. We like how this apartment was modernly designed. The check in and check out process was easy - detailed instruction provided. Would stay again. "
United States
Yue Z.
The price is ￥32,300
￥58,420 total
includes taxes & fees
Jun 1 - Jun 2
The Classic Suite: 2BR close to NYC
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

Executive Inn - Fort Lee

Executive Inn - Fort Lee

8/10 Good
"Stay was quiet"
Fannie 1-night trip
Posted less than an hour ago
Executive Inn - Fort Lee

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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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.

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 Bronx Zoo, 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.