Vacation rentals in Ossining

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Location · Value · Layout

Accord River House

Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.

Value · Family · Hot tub

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.

Location · Value · Hospitality

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Family · Value · Access

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

Value · Location · Layout

Elegant Hideaway: Cozy Cottage in Katonah, NY

Escape to our private, beautifully renovated cottage in the heart of Katonah / Bedford NY area.This standalone gem, separate from the main estate, offers private parking, high-speed WiFi, and a flatscreen TV. Every detail has been expertly designed, from the luxurious furniture to the elegant decor, ensuring a stylish and comfortable stay. Enjoy complete privacy and unwind in a space that combines modern amenities with timeless charm—perfect for a peaceful retreat in a stunning natural setting.

Location · Nearby · Long stay

Boulder Tree House

Boulder Tree House 🌲🌲🌲 SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for an exciting, romantic, unique experience but can accommodate a 3rd person.

Family · Location · Kitchen

Enjoy Summer Living "Stone Haven" Hudson Valley

Luxurious, spacious two story private living quarter located in the Hudson Valley. We offer modern lodging with a brand new small kitchen and bath outfitted with marble including complementary coffee & tea bar. A large living room is a great spot to watch a movie , play a game of pool on the pool table or lounge around after a day of work or leisure. Enjoy amenities, salt water pool, quiet work space with High Speed WiFi. Minutes from hiking & bike path, restaurants, train station to NYC.

Location · Family · Hiking

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: No Kitchen!! Drive, walkway & entrance accessible to full size wheelchair (see photos) but bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

Value · Location · Wifi

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Family · Value · Hospitality

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Location · Value · Check-in

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.

Location · Family · Sleep quality