House holiday rentals in Ossining

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Popular amenities for Ossining house rentals

House rentals with a pool

Guest favourite
Home in Warwick
4.92 out of 5 average rating, 109 reviews

Summer Retreat! Amazing Pool, Playground, 7 acres!

JohanyRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 144 reviews

4Br Mountain Brook House on 130 acres w/ trails

AnnetteRating, 5 stars2 weeks ago
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.
Superhost
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Commack
4.99 out of 5 average rating, 140 reviews

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

AliceRating, 5 stars3 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!
Guest favourite
Home in Greenwich
4.96 out of 5 average rating, 45 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars6 days ago
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
Top Guest favourite
Home in Pound Ridge
5 out of 5 average rating, 164 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MeredithRating, 5 stars1 day 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!
Top Guest favourite
Home in Greenwood Lake
5 out of 5 average rating, 67 reviews

Heated Pool On | Fenced Yard | Hot Tub | Lake View

YadiRating, 5 stars1 week ago
Loved staying here, Fanny was very responsive. The house is so spacious. My girls and I had a blast!
Superhost
Home in Beacon
4.92 out of 5 average rating, 133 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

MarissaRating, 5 stars2 weeks ago
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

Superhost
Home in Croton-on-Hudson
4.73 out of 5 average rating, 15 reviews

Secluded Mid-Century Modern Home

ChrisRating, 5 stars5 days 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.
Superhost
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
Home in Croton-on-Hudson
4.86 out of 5 average rating, 21 reviews

Croton retreat w/ yard + hot tub

BenRating, 5 stars1 week ago
Convenient and easy! Would recommend
Guest favourite
Home in Kerhonkson
5 out of 5 average rating, 272 reviews

Cook House | Modern Cottage w/ Hot Tub & Fireplace

AdamRating, 5 stars4 weeks ago
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.
Guest favourite
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!
Superhost
Home in Piermont
4.82 out of 5 average rating, 94 reviews

Piermont View

PatriciaRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Ossining
5 out of 5 average rating, 44 reviews

Nearaway - Midcentury Modern Cozy Cottage

AmeliaRating, 5 stars2 months ago
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!
Guest favourite
Home in Mount Tremper
4.93 out of 5 average rating, 225 reviews

Mt. Wonder - Hot tub, sauna, wonderful view

DianeRating, 5 stars5 days ago
Wonderful views and lots of space to explore your surroundings. We enjoyed the eco-friendly hot tub the most!

Private house rentals

Superhost
Home in Chappaqua
4.87 out of 5 average rating, 78 reviews

Chic and Cozy 2BD 1920's Cottage Retreat

VanessaRating, 5 stars3 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!
Top Guest favourite
Home in Barryville
5 out of 5 average rating, 17 reviews

Luxury Mountain Retreat with Panoramic Vista Views

PrashantRating, 5 stars1 week ago
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.
Guest favourite
Home in Greenwood Lake
5 out of 5 average rating, 22 reviews

Lakeview House ~ Hot Tub, Firepit, Stunning Views

ScottRating, 5 stars2 days ago
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.
Top Guest favourite
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 favourite
Home in Accord
5 out of 5 average rating, 65 reviews

Accord River House

KacyRating, 5 stars2 weeks ago
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!
Top Guest favourite
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 favourite
Home in Putnam Valley
4.97 out of 5 average rating, 66 reviews

Waterfront Lake House

KayleeRating, 5 stars2 weeks ago
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.
Superhost
Home in Tarrytown
4.84 out of 5 average rating, 37 reviews

Lovely Tarrytown Home in Hudson

DanielleRating, 5 stars1 week ago
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

Destinations to explore

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  5. Ossining
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