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Ossining Vacation Rentals

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Vacation Rentals in Ossining

Stamford Suites
Exterior
Stamford Suites
2.5 star property
6.8 out of 10, 727 reviews
"We loved all the dining options that were just a few minutes walk from the hotel. The hotel is outdated but it was very clean and the suites were spacious. The staff was friendly and helpful. "
The price is $203
$234 total
includes taxes & fees
Jun 28 - Jun 29
Stamford Suites
Waterfront Retreat Center for Health & Wellness
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, 50 reviews
"We stayed at the New Dawn for a Memorial Service. The setting on the water was so peaceful and private, yet easy access for those of us traveling by public transportation from Manhattan and La Guardia airport. We had chairs lined up facing the water for a Celebration of Life Ceremony. The whole downstairs layout was just wonderful with indoor and outdoor areas for people to gather, sharing memories and grief. Food platters from Costco were easily arranged and the weather was perfect. It was so...
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $202
$286 total
includes taxes & fees
Jun 24 - Jun 25
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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Spacious 3BR Private Home * Direct Water View
Beach
Spacious 3BR Private Home * Direct Water View
10.0 out of 10, Exceptional, 13 reviews
"Great stay in New Rochelle! Clean house! Very quaint! Comfy beds! Wonderful property management! Great communication!"
Spacious 3BR Private Home * Direct Water View
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 38 reviews
"My husband and I greatly enjoyed our stay! We mentioned that we were traveling for our honeymoon and upon our arrival, the host had left a bottle of wine and some little decorations on the dining room table to celebrate our marriage! It was so thoughtful and sweet!! The Vrbo itself was cozy and tidy. We enjoyed cooking in the kitchen and listening to the music of Motown on the cd player. Our host was prompt to respond to messages and answered all questions clearly. We loved staying close to so...
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, 105 reviews
"This is a fantastic property and host"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, 3 reviews
"7 bedrooms, most with water views, were perfect for my siblings and me, our spouses and children, and our mother to spend a glorious weekend together! We hosted an unforgettable 80th bday party for our Mom with all our extended family and friends. Wow! The house is gorgeous! It is perfect for a event. The grand hall, the ability to open up the rooms to the backyard, and the VIEW, truly set the stage for a beautiful evening. The home is truly remarkable! My mom was overwhelmed and so thankful...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
The Subterranean Haven
Exterior
The Subterranean Haven
10.0 out of 10, Exceptional, 1 review
"The neighborhood is really nice and clean with a good variety of stores nearby. We found the subterranean haven to be a great location for unwinding and having small events. The George's are incredibly understanding, patient and flexible. We'd definitely recommend this host to anyone."
The price is $180
$180 total
includes taxes & fees
Jun 23 - Jun 24
The Subterranean Haven
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Outdoor dining
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
9.6 out of 10, Exceptional, 44 reviews
"We had a great time celebrating Thanksgiving with our adult children in the Carriage house. The location was great - beautiful neighborhood in small town with easy access to all the things we did in NYC. Lisa helped us when we didn’t have all the right kitchen tools for our meal and worked with us on our schedule for her dog business. It was a real pleasure spending our special family time in this home - comfortable and so many things to do (we played ping pong and pool). Thank you Lisa for a...
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
Property grounds
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
Global Luxury Suites White Plains
Reception
Global Luxury Suites White Plains
3.5 star property
7.6 out of 10, Good, 17 reviews
"If this option is available in the city you are traveling to, take it! You get a home-y, modern APARTMENT with space, rather than a tiny, old hotel room. I always search Global Luxury Suites before searching anything else."
Global Luxury Suites White Plains
Cozy Spacious Guest Suite 15 minutes from NYC
Interior
Cozy Spacious Guest Suite 15 minutes from NYC
6.8 out of 10, 3 reviews
"Quiet neighborhood ample room to relax."
The price is $90
$165 total
includes taxes & fees
Jun 27 - Jun 28
Cozy Spacious Guest Suite 15 minutes from NYC
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Fridge, microwave, oven, stovetop
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
10.0 out of 10, Exceptional, 1 review
"The owner is a verry nice person!!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Mini Garden-Apartment near New York City
Interior
Mini Garden-Apartment near New York City
Mini Garden-Apartment near New York City
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 18 reviews
"Stayed while attending a local wedding and wished we had had more time to hang out at the house! The lake is beautiful and the house had everything we needed! Hope to come back some day!"
Serenity Awaits at this Cozy Lakeside Bungalow
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 63 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, 1 review
"We went to the area to celebrate my husbands 30th birthday with some friends and absolutely loved the home. It was brand new and decorated immaculately. It comfortably fit our group and we thoroughly enjoyed our time there. The hosts were super accommodating and quick to respond. Would absolutely reccomend and go again!"
The price is $499
$916 total
includes taxes & fees
Jun 22 - Jun 23
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Basement Apartment Close to Bus & Metro-North
Interior
Basement Apartment Close to Bus & Metro-North
2.0 out of 10, 2 reviews
"I first the ad promoted 2 bed room and it’s was only one with a person next to you second the owner was horrible with communication check in was at 4 I couldn’t check in until 8 just to view a little room with dead roaches on the sheats and covers I didn’t even stay i simply went to a motel and lost money booking this property the owner say he lock out he can’t give refund"
The price is $105
$150 total
includes taxes & fees
Jun 24 - Jun 25
Basement Apartment Close to Bus & Metro-North
The Safe House - High Tech Apt #2 - 3 Beds
Beach
The Safe House - High Tech Apt #2 - 3 Beds
9.8 out of 10, Exceptional, 30 reviews
"Since it was first time with VRBO, I was a little nervous about the whole process going into it. Rob was great to answer questions and deal with both myself and my granddaughter.It was an ideal location for visiting the Hudson River Valley and along the coast to Newport. We flew into White Plains and it is just a 20 minute ride away. The apartment was clean and convenient. We only ate 3 meals in 5 days away from there. The beds were comfortable and the shower was very nice. I liked the shower...
The price is $202
$321 total
includes taxes & fees
Jul 14 - Jul 15
The Safe House - High Tech Apt #2 - 3 Beds
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
10.0 out of 10, Exceptional, 5 reviews
"The property was as advertised with every amenity imaginable. A good option for doing NYC"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Don't see what you're looking for?
See all available properties in Ossining
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.

Ossining Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Ossining private vacation homes
Known landmarks
Franklin D. Roosevelt State Park, Paramount Hudson Valley Theater and Rockefeller Archive Center
International airports
New York, NY (JFK-John F. Kennedy Intl.) and New York, NY (LGA-LaGuardia)

Other types of properties in Ossining you may be interested in

Armoni Inn & Suites
Restaurant
Armoni Inn & Suites
3.5 star property
6.0 out of 10, 1,261 reviews
"I arrived late at night, and everyone was so sweet. When I got to the room, I didn’t bother checking the lights as I just went to the bathroom and to bed. In the morning the bathroom light did not work. And I was staying two nights, and they accommodated me and got me a whole new room. Thank you! "
The price is $75
$84 total
includes taxes & fees
Jul 2 - Jul 3
Armoni Inn & Suites
Baymont by Wyndham White Plains - Elmsford
Desk, laptop workspace, blackout drapes, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very Good, 1,045 reviews
"Everything was Good."
The price is $125
$143 total
includes taxes & fees
Jul 3 - Jul 4
Baymont by Wyndham White Plains - Elmsford
Royal Regency Hotel
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very Good, 1,540 reviews
"It’s confortable "
The price is $105
$140 total
includes taxes & fees
Jun 30 - Jul 1
Royal Regency Hotel
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.

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 $90 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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: You might want to consider this vacation home rental near Ossining, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Ossining?

With 7 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 Louis Engel Waterfront Park and Teatown Lake Reservation 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.

Recent reviews of Ossining properties
Expedia verified reviews

Courtyard by Marriott Yonkers Westchester County

Courtyard by Marriott Yonkers Westchester County

5/5 Excellent
"Beatiful,Excelent"
A verified traveler stayed at Courtyard by Marriott Yonkers Westchester County
Posted 2 days ago
Courtyard by Marriott Yonkers Westchester County