Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

Cozy 1-bedroom retreat minutes from West Point!

Highland Falls
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is NZ$324
includes taxes & fees
17 Nov - 18 Nov
Cozy 1-bedroom retreat minutes from West Point!

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is NZ$361
includes taxes & fees
24 Nov - 25 Nov
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Stamford Suites

4.0 star property
Downtown Stamford
6.0 out of 10, (72)
"It was great"
United States
Natalie
The price is NZ$248
includes taxes & fees
17 Nov - 18 Nov
Stamford Suites

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Highland Falls
10.0 out of 10, Exceptional, (4)
"The apartment was awesome. Wish we were able to stay for more than just the one night. The host was responding to questions almost before I was done typing the question:) Everything was clean and orderly, parking was close (About 8 inches from the door.) We are picking up more work in the area and hope to stay again next trip."
United States
Peter F.
The price is NZ$497
includes taxes & fees
2 Dec - 3 Dec
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Croton-on-Hudson
10.0 out of 10, Exceptional, (5)
"We had an excellent stay! Our hosts were kind and helpful. The home was modern and very well kept, very clean. I would highly recommend this location and home to anyone traveling in the area."
United States
Suzanne A.
The price is NZ$525
includes taxes & fees
17 Nov - 18 Nov
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is NZ$799
includes taxes & fees
23 Nov - 24 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford
9.6 out of 10, Exceptional, (5)
"We had a great stay at this apartment! It was clean and the location couldn't be better. Communication with the host was easy and timely. I would definitely stay here again and recommend this place to friends/family visiting the Stamford area."
United States
Bobbie-Jo S.
The price is NZ$667
includes taxes & fees
12 Dec - 13 Dec
Modern Luxe 1BR Apt in Downtown Stamford

Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan
9.8 out of 10, Exceptional, (8)
"Very nice! Easy to work with and house was what we expected. "
United States
Jack P.
The price is NZ$684
includes taxes & fees
17 Nov - 18 Nov
Seabreeze at the beach west beach Stamford ct.

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside
10.0 out of 10, Exceptional, (6)
"Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible"
United States
Joanne
The price is NZ$585
includes taxes & fees
17 Nov - 18 Nov
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

45 Minutes from NYC, Entire House near Stamford Downtown,

Downtown Stamford
10.0 out of 10, Exceptional, (19)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
United States
Lisa B.
The price is NZ$723
includes taxes & fees
17 Nov - 18 Nov
45 Minutes from NYC, Entire House near Stamford Downtown,

Spacious 2 bedroom apartment with 1 bathroom and private street entrance

2.0 star property
Paterson
10.0 out of 10, Exceptional, (1)
"The comfort and safety "
United States
Jolena
The price is NZ$453
includes taxes & fees
23 Nov - 24 Nov
Spacious 2 bedroom apartment with 1 bathroom and private street entrance

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Croton-on-Hudson
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay. Very clean updated studio in a perfect location in Croton. Maria was great host and communicated well during our trip."
United States
David P.
The price is NZ$513
includes taxes & fees
8 Dec - 9 Dec
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (126)
"Everything was super clean and the hosts are very easy to deal with. They came and took care of an issue with wasps for us. The view is phenomenal and having the patio to enjoy it from was great. "
United States
Samantha W.
The price is NZ$542
includes taxes & fees
17 Nov - 18 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

New Modern Apartment

Bryn Mawr
10.0 out of 10, Exceptional, (5)
"great place to stay at absolutely comfortable and great neighborhood!"
United States
fransheska r.
The price is NZ$485
includes taxes & fees
1 Dec - 2 Dec
New Modern Apartment

Piermont Oasis

Piermont
9.8 out of 10, Exceptional, (7)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
United States
Anonymous traveller
The price is NZ$370
includes taxes & fees
23 Nov - 24 Nov
Piermont Oasis

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

CROTON HDSN
9.8 out of 10, Exceptional, (90)
"Fabulous place with extraordinary host. Better than advertised, well appointed & thoughtful touches throughout!"
United States
Sherri P.
The price is NZ$590
includes taxes & fees
2 Dec - 3 Dec
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Lovely 3BR Home with parking-Walk to WP Gate!

Highland Falls
10.0 out of 10, Exceptional, (7)
"Celebrated my son’s HS graduation with my father-in-law along for the adventure, Joe’s townhouse is super convenient to Thayer Gate and eating establishments along Main St. Grill worked well and the beds made for sound slumber. For mixed company an extra half bath might be desired, but 3 guys who know each other well managed just fine. The basement washer & dryer are top of line."
United States
James W.
The price is NZ$596
includes taxes & fees
17 Nov - 18 Nov
Lovely 3BR Home with parking-Walk to WP Gate!

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

Highland Falls
10.0 out of 10, Exceptional, (13)
"Great Unit."
United States
Rudy R.
The price is NZ$484
includes taxes & fees
17 Nov - 18 Nov
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

2 DEEP Discounted Apts by American Dream, Sleeps 8

2.0 star property
Hasbrouck Heights
9.4 out of 10, Exceptional, (3)
"The apartment was nice and clean and a designated parking right at the door. The host was very helpful."
United States
Irma E.
The price is NZ$797
includes taxes & fees
29 Nov - 30 Nov
2 DEEP Discounted Apts by American Dream, Sleeps 8

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

Downtown Stamford
9.2 out of 10, Wonderful, (10)
"loved walking the city. pizza was good."
United States
michelle b.
The price is NZ$466
includes taxes & fees
24 Nov - 25 Nov
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access 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 favorite 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 depends 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 NZ$248 per night. Entering your travel dates in the search wizard you might find 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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Sleepy Hollow is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

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.