
House holiday rentals in Ossining
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Top-rated house rentals in Ossining
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Popular amenities for Ossining house rentals
House rentals with a pool

Summer Retreat! Amazing Pool, Playground, 7 acres!
This property is large and roomy with plenty beds to go around including the basement with the pool and ping pong tables plus a home gym with various equipments. The outdoors were fantastic with a very nice temperature controlled pool, Jacuzzi, swings set for the little ones and enough acreage to have a soccer match. The neighborhood was nice and quiet in a great country setting with lots of wildlife to enjoy to include lots of singing birds. Our family reunion was a great success due in part to the before mentioned surroundings. Douglas was always available to resolve minor issues, very responsive and accommodating, thanks for making our stay at this property a great one.

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!

Riverfront Cottage Retreat & Pool 35 mins from NYC
A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!

Heated Pool On | Fenced Yard | Hot Tub | Lake View
Loved staying here, Fanny was very responsive. The house is so spacious. My girls and I had a blast!

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.
Weekly house rentals

Secluded Mid-Century Modern Home
Serene and intentional space, a lovely place to be and stay with family or close friends. Easy access to the sweet town of Croton - on - Hudson on a secluded and particularly beautiful property. Important to note is that you will not just feel at home you will enjoy the comforts of home that are not typical in rental spaces. From the pillows and bedding to the lovely tapestry of natural accents inside and outside the home puts you at peace with the space and lay the foundation for whatever your event and reason for your stay. Exceptional doesn't describe this property but sets it apart among the options in Croton - on - Hudson. We will be back and can't wait. You'll be able to cook at home and stay amidst a peaceful and enjoyable respite from wherever you hail from for whatever reason you are traveling to this area. So pleased with our AIRBNB choice.

Camped Inn at Sundial Farm -- Tiny House
Hi! The house was cute and convenient for our purposes. We were on a tight schedule so could not be there when the utilities could be explained to us which put us at an extreme disadvantage. It's a cute place to get away. Thanks for your hospitality.

Croton retreat w/ yard + hot tub
Convenient and easy! Would recommend

Cook House | Modern Cottage w/ Hot Tub & Fireplace
Staying at Cook House is like staying at a really nice hotel--but out in the country. A lot of AirBnBs have the feel of houses that are flipped on a modest budge; they're newly updated but ultimately not that nice. Cook House is, in contrast, exceedingly nice. The hosts have paid a lot of attention to detail and ensured that everything about the property is really high quality. Communication was excellent. I would definitely stay here again.

Hudson Valley Escape
Staying at this stunning Victorian home in Ossining was an absolute dream. From the moment we walked in, we felt completely at home. The house is full of warmth and character, with so many cozy sitting rooms to choose from — each one with its own unique charm. Every detail of the décor felt thoughtfully chosen, striking a perfect balance between historic charm and comfort. We especially loved relaxing on the back porch, taking in the beautiful view of the Hudson River. Jeff was a fantastic host — so friendly, easy to communicate with, and full of great local tips. His guidebook made exploring the area so much easier, and really helped us make the most of our stay. We couldn’t have asked for a better place or a better host. Highly recommend if you're looking for a special getaway with true character!

Piermont View
We enjoyed our short stay in Piermont. We did a few walks into town to enjoy a few shops and restaurants and lovely view of the new Tappan Zee Bridge. Carolyn was a responsive host and the accommodations were nice, comfortable and clean!

Nearaway - Midcentury Modern Cozy Cottage
Nearaway was a dream! Quiet and cozy and genuinely one of the most unique Airbnb’s I’ve stayed in. James was super communicative and flexible. The area is quiet and gorgeous with lots of bird life and hiking trails just a short drive or walk away. It rained most of the time we were there but I enjoyed just hanging out by the fire and reading. Will definitely be back!

Mt. Wonder - Hot tub, sauna, wonderful view
Wonderful views and lots of space to explore your surroundings. We enjoyed the eco-friendly hot tub the most!
Private house rentals

Chic and Cozy 2BD 1920's Cottage Retreat
Elizabeth’s place was great and we thoroughly enjoyed our stay! It had everything we needed to be comfy with our toddler and dog, and the neighborhood had all we needed as well (close to the train station, great coffee at Bobo’s and Lange’s deli for breakfast and lunch). Elizabeth made sure we got in okay and was very responsive. Thanks!

Luxury Mountain Retreat with Panoramic Vista Views
I am in two minds about what to write in this review. On one hand, this property is truly mind blowing. It has been designed beautifully indoors and there is so much attention to detail. And then, the view…I’ve traveled a lot and the view blew my mind. On the other hand, I’m not sure I want too many other people to know about this gem..because I want to come back. And I am hoping this review doesn’t make that more difficult.

Lakeview House ~ Hot Tub, Firepit, Stunning Views
The home was pristine and beautifully designed, feeling like a brand new home. Everything was purposely placed to have exactly what you would think you’d need. The host is extremely friendly and super responsive. The views of the lake are awesome. The bedrooms are huge and the beds and bedding are extremely cozy (we all slept like babies). The duel decks are a really cool set up with the hot tub on the bottom such a cool vibe with really nice ceiling lights hanging. We came for a work escape as a team, and this was a great stay for us. The bedrooms upstairs also had their own little balconies, which is great to enjoy a morning cup of coffee before getting our day started. They also had all the amenities in the kitchen you could ever need.

Dr. Ruth’s Serene Lake Retreat
After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.

Accord River House
This was hands-down, my favorite. Air B&B ever! We hope to return and spend more time on our next visit. We were literally immersed in and surrounded by nature and it was so beautiful and peaceful. It also felt like home the minute we stepped in… like going to a friend’s “country weekend” place where the books, puzzles, games, records, artwork, handcrafted pottery, electric blankets, dog beds and more (!) just make you feel at ease and in comfort. This place is so loved and it shares that love with its visitors. Thank you to the owners for sharing such a special place!

A nice place to getaway
We’ve stayed at Filiz’s place a few times and it’s perfect! Quiet, clean, and easy to get to where we needed to be. We’ll be back!

Waterfront Lake House
Absolutely beautiful stay, Brian is an amazing host and went above and beyond with instructions and helped whenever needed. Their place is located in such a beautiful area, it is quiet and within 10 min drive to stores. The space is very clean and organized. My guests and I felt right at home.

Lovely Tarrytown Home in Hudson
I am so grateful to Elinisa for taking our reservation same day and accommodating our special requests. The home was perfect for my visit with my 3 kids and seemed well-equipped for a longer stay.
Quick stats about house rentals in Ossining
Total rentals
10 properties
Nightly prices starting at
$62 AUD before taxes and fees
Total number of reviews
290 reviews
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
3 Westerly Bar and Grill, DD's Diner and Louis Engel Waterfront Park
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Gilgo Beach
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo