
House vacation 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

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

4Br Mountain Brook House on 130 acres w/ trails
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !

Harrison FieldBook Book6Nights and 7th Night FREE
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

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!

Modern Lux 5-Bed, Pool Open! Dogs Welcome
The graves home was very comfortable. It was very accommodating. It had enough room for the whole family. We were not on top of each other. The beds were extremely comfortable. The last place we stayed at the beds were horrible. These were absolutely comfortable. It was very peaceful and quiet no surrounding neighbors. It was wonderful to wake up and see the deer in the backyard every morning while I was drinking my coffee. The host was great. He responded within 5 to 10 minutes every time I had no issues would definitely recommend staying here if you’re looking for a quiet, relaxing family getaway. and the pool is wonderful.

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!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

Englewood NJ Country Carriage House (15 min NYC)
Lisa’s place was fun and relaxing for our family. Great place to relax and unwind all while being close to the great areas we visited. Lisa was a great host ❤️
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.

The Best Lake House! *Ask About Boat Use Promo*
This beautiful lake house is a lovely retreat from the chaos of the city. We spent the day lounging by the dock, and relaxing in the sun. It was awesome to have a full private bar with your own pool table right in the house!

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.

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!

Cozy studio Mt Vernon/Bronx NYC kit, bthrm & prkin
A friend and I stayed at this location for a concert and it was the perfect space for two people. Clean and cozy. AC and ceiling fan also, which allows airflow through our. Parking on site is a little snug but still manageable to get in and out of. Check and check out went smoothly!

NEW! Stylish Home in the Heart of Beacon
This was by far one of the most wonderful Airbnb experiences we’ve ever had. We, along with our guests, were impressed by all the thoughtful decor touches in the in the home, the clean space, and the stocked pantry. Plenty of cookware, coffee, tea, etc. if you want to cook in the home. Otherwise it’s just a three minute walk from Main Street and all the wonderful eateries Beacon has to offer. Tatiana was very responsive and welcoming!

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

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!
Private house rentals

Piermont River Front
The location is perfect within Piermont; the home is very nice, and a great value.

Idyllic & Chic in Piermont, 20 min from GW Bridge
Staying here was perfect for us as a family with two very young kids. There is plenty of space and a beautiful garden and patio area. We were able to park the car in a dedicated space which brought us straight onto main street. We had a gorgeous coffee shop on our doorstep where we got our tasty breakfast treats, and there are so many lovely spots to eat just a stones throw away. Highly recommend the Piermont Creamery for ice cream! We were there every afternoon! We stayed in Piermont before and it’s such a peaceful and friendly town. Mekdem was so responsive with all our questions and again herself and Skip were such lovely hosts. The house had everything we needed which was great just open the door and make ourselves at home. Highly recommend!

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.

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
We had a great long weekend stay at Brian's place with our dog. The view of the lake from the house was incredible. The entrance down the stairs gave us a very private area for us to spend time enjoying the surroundings. The place itself was very clean, had everything we needed and Brian was great at communication the whole time. We couldn't believe this was only an hour or so drive from NYC. We would definitely stay again!

Hartsdale Escape: 35 minutes to midtown Manhattan
This was a great place to stay if you are in need of a place to stay for only a couple nights. It is clean and cozy. I will say the bathroom is a little tight but other than that no complaints. It seems like the messages I received from the host were automated but they were helpful. I sent a couple messages but they were not answered. Although they were no important it would have been nice to receive a reply.

Quaint Cottage in the Woods
This location is truly nestled in the woods. The guest has a designated parking space on the road in front of the unit as the owners use the driveway adjacent to the unit for their cars which makes it a little less convenient for renters with bags, but not impossible. Thereafter, the unit is a great find for mid-north Westchester County. Well stocked, comfortable beds, great TVs. Unit seems to be located somewhere near a gun range, which was disconcerting on Sunday morning upon waking tp consistent gunfire. Not Jenna's fault but would have been good to get a heads up. Jenna couldn't have been nicer or more responsive during our stay and was graciously accomodating when our return flight was cancelled by giving us a later checkout. Would recommend this property without hesitation.

Mountain Top Retreat
Andre's place was a beautiful home away from home. Sparkling clean inside and surrounded by serene natural beauty outside. Bring your bug spray if you're going for a hike!
Quick stats about house rentals in Ossining
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
290 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, 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