Holiday rentals 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.

Hudson Valley Escape

This sun-infused Queen Victorian home with front wisteria-draped porch and stunning Hudson River views will charm you. The home offers a library, two living rooms, renovated kitchen with butlers pantry and back staircase, 4 bedrooms and 2.5 baths. This home has many entertainment possibilities with 2 covered porches for dining, BBQ or just lounging and admiring the river views. A pleasant 10 minute walk to the train station. Just 45 minutes by gorgeous riverside train ride to Grand Central.

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.

Charming Studio Apartment

Enjoy this beautiful quiet studio apartment in Cortlandt Manor. Private designated parking space, private keyless entrance, washer dryer, large closet space, brand new 4K TV with access to multiple streaming apps including Netflix, Hulu, Max, and Peacock. Queen size bed, small dining table and kitchen with utensils and cooking supplies. Keurig coffee maker with complimentary pods provided. Sliding glass doors lead to a large open deck with BBQ for use and 2 Adirondack chairs.

Cozy tiny log cabin on 13 acres

Tiny rustic cabin located in the woods. Large screen TV and Wi-Fi. No stove but will provide cooktop and toaster. Full bathroom with shower. People love the back deck to enjoy their morning coffee and to watch for wildlife. One bedroom with comfy queen bed and fan. All linens and towels supplied. Please be aware this is a rustic beautiful site. Trails in the back and very close to rail trail. Mini splits will keep you toasty warm in the winter and ice cold in the summer.

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!

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!

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:)

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.