Sleepy Hollow Holiday Rentals

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Our top choices for Sleepy Hollow holiday rentals

10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AU$470
includes taxes & fees
3 Mar - 4 Mar
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$429
includes taxes & fees
8 Mar - 9 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
2.0 star property
The price is AU$401
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (10 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is AU$537
includes taxes & fees
4 Mar - 5 Mar
Seabreeze at the beach west beach Stamford ct.
7.6 out of 10, Good, (4 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.
The price is AU$220
includes taxes & fees
2 Mar - 3 Mar
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Holiday Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is AU$580
includes taxes & fees
2 Mar - 3 Mar
Contemporary Cozy Cottage
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is AU$445
includes taxes & fees
8 Mar - 9 Mar
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
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.
The price is AU$268
includes taxes & fees
16 Mar - 17 Mar
Cozy 1-bedroom retreat minutes from West Point!
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AU$430
includes taxes & fees
2 Mar - 3 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (10 reviews)
"Clean, modern, convenient property. Online pictures were accurate, check in was easy. Highly recommend. Would stay there again without hesitation."
United States
Rebecca
The price is AU$520
includes taxes & fees
2 Mar - 3 Mar
Gorgeous, 2- bedroom apartment walking distance to GWB!
10.0 out of 10, Exceptional, (30 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$545
includes taxes & fees
2 Mar - 3 Mar
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is AU$529
includes taxes & fees
2 Mar - 3 Mar
Elegant Hideaway with Free Parking

Holiday Home in Cove - East Side - Shippan

New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
The price is AU$1,213
includes taxes & fees
6 Mar - 7 Mar
New Beach Home near Stamford Downtown/Shippan
10.0 out of 10, Exceptional, (2 reviews)
"Our stay in Edgewater was incredible. The house is so beautiful and lovely. Abby & Mary are incredible. We world be back soon. "
United States
ariel n.
The price is AU$277
includes taxes & fees
9 Mar - 10 Mar
Affordable NYC Luxury: Warm & Inviting Stay, Walk to Riverside Views
10.0 out of 10, Exceptional, (1 review)
"The comfort and safety "
United States
Jolena
The price is AU$318
includes taxes & fees
4 Mar - 5 Mar
Private 2-bedroom apartment, private entrance, MetLife Stadium World Cup 30 mins
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.
The price is AU$459
includes taxes & fees
11 Mar - 12 Mar
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
The price is AU$985
includes taxes & fees
2 Mar - 3 Mar
Comfortable 1 family home in Tuckahoe that's near train
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$505
includes taxes & fees
2 Mar - 3 Mar
The Classic Suite: 2BR close to NYC
3.0 star property
The price is AU$529
includes taxes & fees
2 Mar - 3 Mar
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Holiday Home in Highland Falls

Lovely 3BR Home with parking-Walk to WP Gate!
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.
The price is AU$482
includes taxes & fees
23 Mar - 24 Mar
Lovely 3BR Home with parking-Walk to WP Gate!
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$225 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 WiFi 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 Westchester Skating Academy, 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.