Holiday rentals in Ossining

Spacious, private retreat 45 mins to NYC

Private, spacious, woodland views, perfect writer's retreat, romantic getaway, or space to chill! Ground-floor apartment in single-family home on 5 acres, 45 mins from NYC. 900 sq. feet of space. Full kitchen, 1 large bedroom, king-size bed & fun bunkbed. Premium bedding, fresh towels, toiletries. Simple, healthy breakfast, coffee, tea, fruit, drinks and snacks provided. 2 miles to Mt Kisco Metro North Station. EV charger. Walk to local nature reserves. 5 mins drive to restaurants and shops.

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.

Charming 18th-Century Farm Cottage

Lovely 18th-century cottage on our vibrant farm 50 minutes North of NYC. Excellent base for exploring the City & the lower Hudson Valley, or for visiting the area for a work or family event. Inspiring & grounding space for working from home, an ideal retreat for artists & writers! NOTE: Maximum occupancy is 1 couple or 2 individuals. Gatherings w/extra people for the day are not possible. We do not allow children under 12, cottage isn't set up for kids & our property isn't suitable for them.

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.

Mountain Edge: Spacious Suite

Mountain Edge: We are excited to welcome you to our Private-Guest Suite located 2 minutes from the Stunning Croton Dam and a 45 minute train ride into the city. Mountain Edge is a 2 bed, 2 bath, suite nestled into the forest. The Croton Dam offers excellent hiking, family & Pet friendly park, and beautiful views, while being just 2 miles to the Village. One queen bed and pullout couch. We do have an additional mattress available by request. We can place in unit ahead of arrival.

Hudson Valley Bungalow Retreat ~1 hr from NYC

Welcome to our light-filled Hudson Valley bungalow in Croton-on-Hudson, just one hour from NYC by train or car. This comfortable, lived-in home is designed for easy stays, quiet downtime, and time outdoors. Enjoy a fully stocked chef’s kitchen, cozy living areas, and space to relax after exploring the river, trails, or town. Ideal for weekend escapes, remote work, or longer stays, the house offers privacy, fast Wi-Fi, and a peaceful setting that makes it easy to settle in.

Charming Studio Centrally Located in Pleasantville

Private Studio Apartment with private entrance. Queen-sized bed + sofa bed. Cozy-space w/ big windows in a big home centrally located in the beautiful small town of Pleasantville. 5 min walk to MetroNorth Train to NYC (45 train ride), Pace University, TONS of bars & restaurants, coffee shops, Jacob Burns Film Center, cute shops. One of the best walking towns in Westchester County. Amazing outdoor activities close by. Friendly host nearby in main house for any questions!

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Croton Quarters-Modern Amenities

Fully renovated with high-end appliances. Free PARKING. Two TVs, NFLX & 6 platforms. XBOX Ser X with games. Fast WIFI. Bd1: queen, 55" TV. Bd2: queen. Office area (desk, fast wifi). Private yard. 7 min walk to restaurants. Car rental nearby. 45 min train to Grand Central. Apt is 1.9mi to train, supermarket. Hiking. I LIVE UPSTAIRS. Multifamily building, there may be occasional noise from upstairs neighbors, such as footsteps.

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:)

Lovely | Private | Historic Home | Walk to Town

Our home is located in the heart of lower Hudson Valley and a quick drive to attractions in neighboring Sleepy Hollow and Croton-on- Hudson. Set in the charming, historic Upper Village neighborhood just a stones throw from downtown Ossining this garden-view apartment occupies part of the second floor of our village colonial and has a private entrance up a set of stairs in our back garden.

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb