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Ossining Vacation Rentals

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Our top choices for Ossining vacation rentals

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
$806 nightly
The price is $898
Jan 5 - Jan 6, 2026
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow

1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
2.0 star property
Ossining
$256 nightly
The price is $292
Jan 4 - Jan 5, 2026
Total with taxes and fees
1BR Queen near NYC | Trails, Biking & Sauna Bliss

Polished 1BR w/ Accessible Room Features + Sauna

Polished 1BR w/ Accessible Room Features + Sauna
2.0 star property
Ossining
$255 nightly
The price is $291
Jan 4 - Jan 5, 2026
Total with taxes and fees
Polished 1BR w/ Accessible Room Features + Sauna

Near NYC! | Stylish Guestroom

Near NYC! | Stylish Guestroom
2.0 star property
Ossining
$268 nightly
The price is $305
Jan 4 - Jan 5, 2026
Total with taxes and fees
Near NYC! | Stylish Guestroom

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very Good, (22)
"Great service and very clean 👌 "
United States
JEAN
$83 nightly
The price is $96
Dec 27 - Dec 28
Total with taxes and fees
The Mansion Hotel-style

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (82)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
$110 nightly
The price is $127
Dec 25 - Dec 26
Total with taxes and fees
Stamford Suites

Charming Apartment in Quiet Neighborhood

Charming Apartment in Quiet Neighborhood
Tappan
10.0 out of 10, Exceptional, (20)
"The location was perfect for our visit and the apartment was immaculately clean and well stocked."
United States
Claudia M.
$168 nightly
The price is $187
Jan 14 - Jan 15, 2026
Total with taxes and fees
Charming Apartment in Quiet Neighborhood

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (5)
"A clean and convenient place to stay for visiting our cadet at West Point. Our hosts were very communicative and helpful. The home and parking situation was just as described. Nice quiet neighborhood, well maintained home. Hearing the babbling broom outside the living room window was very relaxing. Plan on staying here again!"
United States
Maria L.
$305 nightly
The price is $319
Dec 24 - Dec 25
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (10)
"Easy check in; quick access to NYC. "
United States
Leah B.
$189 nightly
The price is $211
Jan 11 - Jan 12, 2026
Total with taxes and fees
Piermont Oasis

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
10.0 out of 10, Exceptional, (3)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
$366 nightly
The price is $371
Dec 24 - Dec 25
Total with taxes and fees
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!

Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!
Englewood
6.8 out of 10, (15)
"It was very clean and in a great area. "
United States
Kyle
$167 nightly
The price is $184
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!

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, (14)
"Great Unit."
United States
Rudy R.
$263 nightly
The price is $266
Jan 20 - Jan 21, 2026
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

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, (5)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
$254 nightly
The price is $281
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

JayZero

JayZero
2.0 star property
Bryn Mawr
$232 nightly
The price is $260
Jan 5 - Jan 6, 2026
Total with taxes and fees
JayZero

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, (90)
"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.
$254 nightly
The price is $290
Dec 28 - Dec 29
Total with taxes and fees
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
7.6 out of 10, Good, (5)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
$338 nightly
The price is $382
Dec 25 - Dec 26
Total with taxes and fees
3BR West Point Retreat-3min to Back Gate+ King Bed

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$256 nightly
The price is $277
Dec 26 - Dec 27
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
$322 nightly
The price is $365
Dec 24 - Dec 25
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
$217 nightly
The price is $245
Jan 19 - Jan 20, 2026
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
$287 nightly
The price is $322
Jan 12 - Jan 13, 2026
Total with taxes and fees
Spacious 3BR Luxe Escape near 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 Ossining Hotel Reviews

Find out more about Ossining

Everything you need to know about Ossining vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ossining vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Ossining vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ossining vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossining. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ossining in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ossining rentals

At Expedia, we put the best Ossining vacation 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 Ossining 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 Ossining vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossining. 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 vacation rental in Ossining?

Yes, there are vacation rentals close to well known attractions in Ossining, or you can go with a more remote option if you're looking for a relaxing stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

What's the top vacation rental that Ossining has to offer?

3BR Prime Luxury near NYC w Arcade Room: You might want to consider this vacation rental near Ossining, which is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Ossining?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Teatown Lake Reservation and Merchants Square are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Thomas J. Watson Research Center are other places to visit while you're in town.

What’s a vacation rental in Ossining like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Ossining. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.