Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday rentals

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 AU$463
includes taxes & fees
1 June - 2 June
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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 AU$502
includes taxes & fees
1 June - 2 June
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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 AU$452
includes taxes & fees
3 June - 4 June
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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 AU$325
includes taxes & fees
3 June - 4 June
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, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is AU$428
includes taxes & fees
3 June - 4 June
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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 AU$571
includes taxes & fees
17 June - 18 June
Bright&Comfy 2bed/1ba in quiet White Plains duplex

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 AU$190
includes taxes & fees
1 June - 2 June
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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 AU$521
includes taxes & fees
3 June - 4 June
Gorgeous, 2- bedroom apartment walking distance to GWB!

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

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 AU$577
includes taxes & fees
3 June - 4 June
Modern Luxe 1BR Apt in Downtown Stamford

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 AU$575
includes taxes & fees
1 June - 2 June
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is AU$291
includes taxes & fees
15 June - 16 June
Piermont Oasis

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is AU$628
includes taxes & fees
28 June - 29 June
Stamford Hideaway w/ Fire Pit

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 AU$438
includes taxes & fees
1 June - 2 June
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

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 AU$583
includes taxes & fees
1 June - 2 June
Contemporary Cozy Cottage

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

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is AU$315
includes taxes & fees
4 June - 5 June
Harriman Outdoor Center - Mountain Laurel Cabin

'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 AU$442
includes taxes & fees
14 June - 15 June
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

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 AU$358
includes taxes & fees
8 June - 9 June
Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins

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 AU$507
includes taxes & fees
1 June - 2 June
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

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$238 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Sleepy Hollow is located next to a golf course, and has a balcony, a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

How many holiday rentals are there in Sleepy Hollow?

Choose from 3 Expedia holiday rentals in Sleepy Hollow for a memorable holiday.

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 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.