Holiday rentals in Ossining

4.85 out of 5 average rating, 145 reviews

Home in Ossining

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

4.99 out of 5 average rating, 196 reviews

Cottage in Cortlandt

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

4.8 out of 5 average rating, 168 reviews

Flat in Peekskill

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Guest suite in Croton-on-Hudson

4.92 out of 5 average rating, 134 reviews

The Bluestone - Spacious 2 bedroom w/central air

Come stay with us! You will have the entire first floor to yourself but we will be right upstairs if you should need us! Access to tree lined back yard with fire pit. Close to metro north train to NYC. Minutes to kayaking, hiking, restaurants, cafes & historical sites. Please note: Drive, walkway and entrance accessible to full size wheelchair (see photos) however the bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

4.96 out of 5 average rating, 318 reviews

Guest suite in Chester

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

4.9 out of 5 average rating, 190 reviews

Home in Peekskill

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.92 out of 5 average rating, 253 reviews

Guest suite in Tarrytown

Stylish Tarrytown Studio | Walk to Train & Main St

Modern designer studio 1 block from Main St, 8-min walk to Metro-North (35 mins to NYC). Private entrance, fast Wi-Fi, full kitchen, Queen bed + King sofa bed. Small front yard for a breath of fresh air. Walk to restaurants, cafes, and Hudson River parks. Ideal for couples, solo travelers, and remote workers. Explore charming Tarrytown, Sleepy Hollow, Rockefeller trails, and the Hudson Valley. A stylish, comfortable base for your next getaway!

Guest suite in Haverstraw

4.94 out of 5 average rating, 365 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

4.83 out of 5 average rating, 127 reviews

Flat in Nyack

Nyack Retreat

This stylish apartment is tucked away but right in the center of the popular town of Nyack. Very comfortable and spacious, perfect for an amazing get away. Please note: This is a quiet multi-family home that houses four apartments. We do not allow any parties or gatherings. Please do not book this place if you plan to host an event. Only persons booked are allowed without permission. Thank you respectfully.

4.64 out of 5 average rating, 75 reviews

Flat in Ossining

Cozy Apartment w/Private Entrance in Ossining Home

Separate entrance and private access to the space. 1 bedroom, private hallway and bathroom with kitchenette/fridge. Located in Ossining NY, Westchester County. 10-15 minutes to the Ossining Train Station and 40 min by train to NYC. Within walking distance to shopping and public library. Wifi provided upon check in. Basic toiletries and amenities provided. Light cooking.

4.91 out of 5 average rating, 204 reviews

Cottage in Mohegan Lake

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.

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Other great holiday rentals in Ossining

5 out of 5 average rating, 14 reviews

Home in Valhalla

Valhalla Home

BethRating, 5 stars1 week ago

This is an outstanding house and Ben is an excellent host. I would stay here again in a heartbeat and would recommend to anyone looking for a quiet, comfortable place to stay in Westchester.

Private room in Hawthorne

4.83 out of 5 average rating, 107 reviews

Clean and cozy attic room

CatherineRating, 5 stars1 month ago

Staying at Ivone's place is like staying at the house of a really cool friend. Lovely thoughtful touches of decor throughout, peaceful chimes outside, smelled fantastic. We were very comfortable. We had a wedding to attend so didn't stay inside the house much, but Ivone was so helpful, and even lent me a spot of nail polish last minute so we didn't have to be late. Highly recommend. Would definitely stay again if we were visiting the area.

4.9 out of 5 average rating, 113 reviews

Private room in Nyack

Cul-de-sac 1-bedroom, includes free parking.

LeighRating, 5 stars4 weeks ago

Jaime's place was just what we needed; a clean, quiet, comfortable place to "crash" for the night! :)

5 out of 5 average rating, 14 reviews

Private room in Ossining

Tranquil Room in Ossining

CirannoRating, 5 stars7 months ago

Nickesha was super friendly, flexible, and accommodating. Her place is great and the room’s view is beautiful. By far the best Air Bnb bed we had this trip!! We hope to be back soon!

5 out of 5 average rating, 17 reviews

Yurt in Ossining

Private Glamping Oasis

YasminRating, 5 stars2 weeks ago

muy cómoda y tranquila hace frío en la noche necesita un calentador pero después de hay todo muy bueno

Private room in Sleepy Hollow

4.98 out of 5 average rating, 109 reviews

Aleida'house on beautiful town.

BeatriceRating, 5 stars1 month ago

My 5 night stay at Aleida’s in Tarrytown was fantastic. Aleida was a very helpful and friendly host, I felt very at home with her. Aleida always replied to any questions promptly. The house is in a great location, only about 5 minutes walk from the station. It is also very close to the river Hudson, and you can do a beautiful riverside walk to see the Tappan Zee bridge and Sleepy Hollow lighthouse. As a woman travelling on my own, I felt very safe in Tarrytown. A couple of times I got the train back from Grand Central late at night, and I always felt comfortable walking back from Tarrytown station to the house. I also felt safe walking around the town in the evening. It’s a very safe and friendly place, and only a 50 minute train to Grand Central. There are plenty shops and things to do in the town too. I would recommend booking a show at the historic Tarrytown Music Hall - it’s really special. I will miss my chats over breakfast with Aleida and would love to come back one day.

4.92 out of 5 average rating, 237 reviews

Private room in Elmsford

1-1 INSIDE OF new Westchester home

ArjunRating, 5 stars3 weeks ago

This place is absolutely gorgeous and very well maintained. Very clean. In a beautiful neighborhood and parking available on property. The hosts are responsive and available when in need. Theres a cute puppy in the house for dog lovers. Will definitely be back here whenever needed.