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

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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
The price is AU$473
includes taxes & fees
20 July - 21 July
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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, (41 reviews)
"rooms were lovely and spacious and hosts were responsive and helpful. "
United States
nina a.
The price is AU$493
includes taxes & fees
20 July - 21 July
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

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$354
includes taxes & fees
22 July - 23 July
Piermont Oasis

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (3 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$383
includes taxes & fees
29 July - 30 July
Cozy 1-bedroom retreat minutes from West Point!

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (9 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AU$753
includes taxes & fees
29 July - 30 July
Fabulous 3bdrm Home w/parking!

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is AU$788
includes taxes & fees
20 July - 21 July
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

Harriman Outdoor Center - Mountain Laurel Cabin

Harriman Outdoor Center - Mountain Laurel Cabin
Haverstraw
The price is AU$369
includes taxes & fees
22 July - 23 July
Harriman Outdoor Center - Mountain Laurel Cabin

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.6 out of 10, Exceptional, (23 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AU$475
includes taxes & fees
7 Aug - 8 Aug
Quiet Apt with Coffee Bar, 1/2 Mile to 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 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is AU$448
includes taxes & fees
18 July - 19 July
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (32 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.
The price is AU$589
includes taxes & fees
21 July - 22 July
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
White Plains
9.2 out of 10, Wonderful, (16 reviews)
"Great place for a short visit to the city "
United States
Jeremy S.
The price is AU$1,040
includes taxes & fees
27 July - 28 July
3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is AU$1,023
includes taxes & fees
22 July - 23 July
3 Mi to Downtown: Spacious White Plains Home

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, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is AU$627
includes taxes & fees
29 July - 30 July
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

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.
The price is AU$489
includes taxes & fees
21 July - 22 July
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (18 reviews)
"Sweet abode. Cozy, clean and amazing location. The cute coffee bar was a nice bonus. Would definitely stay there again. "
United States
Danica J.
The price is AU$699
includes taxes & fees
21 July - 22 July
Local Artist Inspired | Walk to WestPoint + King Bed

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, (8 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is AU$503
includes taxes & fees
10 Aug - 11 Aug
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (35 reviews)
"Our stay was very nice and described as listed! We recommend anyone who is interested to stay! "
United States
Aj L.
The price is AU$594
includes taxes & fees
27 July - 28 July
Contemporary Cozy Cottage

Private Garden Getaway: Cozy & Chic , Near Subway

Private Garden Getaway: Cozy & Chic , Near Subway
Manhattan
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, excellent location and our host was so helpful and immediately responsive to any of my husband's requests while he was there. We would most definitely stay here again! "
United States
Robin C.
Private Garden Getaway: Cozy & Chic , Near Subway

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$195
includes taxes & fees
21 July - 22 July
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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$493
includes taxes & fees
23 July - 24 July
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$245 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?

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

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 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 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.