House vacation rentals in Ossining

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Popular amenities for Ossining house rentals

House rentals with a pool

Top guest favorite
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars4 months ago
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!
Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck
4.89 out of 5 average rating, 145 reviews

4Br Mountain Brook House on 130 acres w/ trails

eveRating, 5 stars2 weeks ago
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 135 reviews

Harrison FieldBook Book6Nights and 7th Night FREE

EmmaRating, 5 stars4 weeks ago
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!
Guest favorite
A private heated pool is surrounded by a wooden deck, featuring two red lounge chairs. Volleyball nets are set up across the pool, which is framed by lush greenery and a large umbrella providing shade. Clear blue water reflects the bright sky.
Home in Commack
4.99 out of 5 average rating, 140 reviews

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

AliceRating, 5 stars4 weeks ago
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!
Superhost
An aerial view captures a stylish retreat surrounded by lush greenery. A wooden deck outlines a rectangular saltwater pool, accompanied by lounge chairs and large umbrellas. A shaded seating area is positioned nearby, promoting outdoor relaxation.
Home in Kerhonkson
4.93 out of 5 average rating, 117 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

KimRating, 5 stars4 days ago
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.
Top guest favorite
A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.
Home in Pound Ridge
5 out of 5 average rating, 164 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MeredithRating, 5 stars4 days ago
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!
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars6 days ago
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.
Guest favorite
A charming carriage house features large windows and a high peaked roof, set amidst lush greenery. A well-maintained pool with a gentle fountain is situated in front, surrounded by landscaped gardens and inviting white lounge chairs.
Home in Englewood
4.94 out of 5 average rating, 158 reviews

Englewood NJ Country Carriage House (15 min NYC)

SarahRating, 5 stars2 weeks ago
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

Superhost
A modern single-story home is set within a lush green landscape. A gravel driveway leads to the entrance, bordered by colorful landscaping and a small garden. Large windows offer natural light, while trees surround the property, creating a sense of privacy.
Home in Croton-on-Hudson
4.75 out of 5 average rating, 16 reviews

Secluded Mid-Century Modern Home

ChrisRating, 5 stars1 week ago
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.
Guest favorite
A sunlit deck overlooks the serene lake, featuring a glass-top table and comfortable seating. Flower pots add color, while the gentle waves can be seen against the wooden dock. The expansive waterway and surrounding hills create a peaceful backdrop.
Home in Greenwood Lake
4.97 out of 5 average rating, 186 reviews

The Best Lake House! *Ask About Boat Use Promo*

KevinRating, 5 stars1 month ago
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!
Superhost
A bright sitting area showcases a light pink custom sofa, complemented by an array of decorative shelves. Natural light enters through large windows, highlighting the wooden flooring. A ladder leads to the loft, and a cooler is positioned centrally on the floor, adding to the homey feel.
Home in Ossining
4.89 out of 5 average rating, 56 reviews

Camped Inn at Sundial Farm -- Tiny House

MonicaRating, 5 stars7 months ago
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.
Superhost
A cozy living room is depicted with light-colored walls and wooden flooring. Two dark armchairs and a light sectional sofa surround a black coffee table. A vase of fresh tulips sits on the table, adding color. Large windows illuminate the space, showcasing a warm, inviting ambiance.
Home in Chappaqua
4.87 out of 5 average rating, 78 reviews

Chic and Cozy 2BD 1920's Cottage Retreat

VanessaRating, 5 stars4 weeks ago
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!
Superhost
A spacious bed with crisp white bedding is centered on a textured area rug featuring a wave pattern. A turquoise feature wall provides a calming backdrop, while a sleek ceiling fan and soft lighting enhance the ambiance. A cozy seating area is positioned in the corner.
Home in East Bronx
4.86 out of 5 average rating, 179 reviews

Cozy studio Mt Vernon/Bronx NYC kit, bthrm & prkin

BriyithRating, 5 stars4 weeks ago
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!
Top guest favorite
A modern living area features a gray sofa with tufted seating, positioned near a wooden coffee table. Exposed wooden beams span the ceiling, while a cozy rattan chair adds warmth. Natural light streams through windows, creating a bright and airy ambiance.
Home in Beacon
4.99 out of 5 average rating, 138 reviews

NEW! Stylish Home in the Heart of Beacon

AlexRating, 5 stars2 weeks ago
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!
Superhost
A single-story red brick house is framed by lush greenery and mature trees. A path leads to the front door, which features a wood frame and decorative glass. The yard is well-maintained, with manicured shrubs and a grassy area visible.
Home in Croton-on-Hudson
4.86 out of 5 average rating, 21 reviews

Croton retreat w/ yard + hot tub

BenRating, 5 stars2 weeks ago
Convenient and easy! Would recommend
Guest favorite
An inviting living area features dark wood paneled walls and a coffered ceiling. A soft, light-colored rug covers the floor, contrasting with a classic leather sofa. Large windows allow natural light to fill the space, with a holiday tree adding warmth to the corner.
Home in Ossining
4.89 out of 5 average rating, 35 reviews

Hudson Valley Escape

KellyRating, 5 stars1 month ago
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

Guest favorite
A modern kitchen design features a central island with seating for three. The space is bright, illuminated by pendant lights, with contemporary cabinetry and stainless steel appliances. A textured backsplash adds visual interest, while large windows allow natural light to fill the area.
Home in Piermont
4.88 out of 5 average rating, 34 reviews

Piermont River Front

StevenRating, 5 stars1 month ago
The location is perfect within Piermont; the home is very nice, and a great value.
Top guest favorite
A modern living room is showcased with a large sectional sofa adorned with vibrant patterned cushions. A coffee table is positioned on a richly colored area rug. The walls are decorated with framed artwork, and natural light illuminates the space through two windows.
Home in Piermont
4.96 out of 5 average rating, 52 reviews

Idyllic & Chic in Piermont, 20 min from GW Bridge

KelleyRating, 5 stars2 weeks ago
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!
Top guest favorite
An open-concept living space features high wooden beam ceilings and a stone fireplace. Large windows provide ample natural light and scenic views of the lake. A staircase leads to an upper level, while a cozy seating area is arranged nearby, emphasizing relaxed living.
Home in Putnam Valley
5 out of 5 average rating, 10 reviews

Dr. Ruth’s Serene Lake Retreat

EvanRating, 5 stars5 months ago
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.
Top guest favorite
A stone patio is shown with six colorful chairs arranged around a fire pit. In the background, trees and a trampoline are visible, contributing to a serene outdoor setting, ideal for gathering and relaxation.
Home in Mohegan Lake
4.95 out of 5 average rating, 57 reviews

A nice place to getaway

LizRating, 5 stars2 months ago
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!
Guest favorite
A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.
Home in Putnam Valley
4.97 out of 5 average rating, 67 reviews

Waterfront Lake House

ConorRating, 5 stars1 day ago
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!
Superhost
A modern studio space is furnished with a large bed topped with decorative pillows. A flat-screen TV is positioned on a media console, complemented by a blue mini fridge and a microwave. Soft light illuminates the room, highlighting a patterned area rug on the floor.
Home in Hartsdale
4.87 out of 5 average rating, 53 reviews

Hartsdale Escape: 35 minutes to midtown Manhattan

DavidRating, 5 stars3 weeks ago
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.
Guest favorite
A serene outdoor deck features two lounge chairs and two armchairs, providing comfortable seating. Potted plants display vibrant flowers, adding a pop of color to the scene. Fallen leaves dot the wooden surface, and natural surroundings are visible from the deck.
Home in Briarcliff Manor
4.95 out of 5 average rating, 38 reviews

Quaint Cottage in the Woods

ArthurRating, 5 stars2 months ago
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.
Top guest favorite
A single-story cottage is shown surrounded by lush greenery. Solar panels are installed on the roof. The entrance features a small set of stairs leading to a front porch with steps flanked by shrubs. Red shutters accentuate the windows, offering a welcoming appearance.
Home in Cold Spring
5 out of 5 average rating, 44 reviews

Mountain Top Retreat

RachelRating, 5 starstoday
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

Destinations to explore

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  5. Ossining
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