Holiday rentals in Ossining

Garden On The Hudson

Experience this family-friendly historic neighborhood nestled within a quaint, safe town. Short drive to the train station/NYC. Its lovely location allows quick access to restaurants, shops, & transportation. Stylish apartment ready to provide you with everything you need for a perfect stay... • 3 Comfortable Bedrooms & 1 Full Bathrooms • Fully Equipped Kitchen w/ Coffee Bar • Beautifully designed and lavishly furnished • Large Smart 4K TVs/High-Speed Wi-Fi • Private lot & Street Parking

Private Hudson River Suite | 48 Min to NYC

Relax in a private guest suite near the Hudson River, designed for comfort, privacy, and a memorable Hudson Valley stay. Enjoy a private entrance, cozy bed, kitchenette, fast Wi-Fi, and dedicated on-site parking. Only 4 minutes from Croton Harmon Station, with Grand Central only 2 scenic express stops away. Ideal for weekend escapes, business travel, or exploring the beauty of the Hudson Valley. Nestled in a safe, peaceful neighborhood near riverfront walks, trails, restaurants, and attractions.

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.

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!

The Hollow Inn at Sleepy Hollow

The Hollow Inn, a charming retreat nestled in the heart of historic Sleepy Hollow—just 45 minutes from NYC and a 15-minute stroll from the Tarrytown train station. Whether you're planning a festive fall getaway with a large family or a peaceful couples’ retreat, this cozy spot is the perfect home base. October is truly magical here, Sleepy Hollow comes alive with Halloween festivities, haunted hayrides, lantern-lit cemetery tours, and more. Book your stay and experience the legend for yourself!

Serene Retreat in the Hills w/Jacuzzi

Forget your worries in this spacious and serene space. Only a 50 minute train ride from Grand Central Terminal in downtown New York City, yet be awakened by song birds in the morning. A private road setting, with nature surrounding you. Minutes away from a rail trail, downtown Mount Kisco, restaurants, groceries, shopping and more. Westchester County Parks provide various hiking, farms & golf courses for you to explore. Monthly stays preferred, & certainly welcome the week long travelers.

Hudson Valley Fall Escape · 50min to NYC · 3 Acre

Willoway is your private 3+ acre Hudson Valley retreat — an oasis for you and friends from the grind of NYC. Woodland quiet, privacy, all 50 minutes from Grand Central by train. Chase away the chill by the gas fire pit, enjoy the dozens of games, books, or records, explore the historic Hudson Valley, and fall asleep by the stone fireplace. Three bedrooms sleep six. Single-level home, gated drive, self check-in, dogs welcome. In my family for 60+ years and still cherished — now yours to enjoy.

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.

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.

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.

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.

Forest Suite | Croton Dam Trails | 45 Min NYC

Mountain Edge: Unplug in your own private forest suite — just 45 minutes from Manhattan. Wake up to birdsong, explore the Croton Dam trails, and return to a spacious, peaceful retreat that feels worlds away from the city. Private-Guest Suite located 2 minutes from Croton Dam and a 45 minute train into the city. Mountain Edge is a 2 bed, 2 bath, suite nestled into the forest. One queen bed and pullout couch. We do have an additional mattress available by request.