Ossining(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Ossining, the top choice for families is Marriott Resort Ossining, located near the Hudson River and St. John's Church. This hotel features a kids' activity room, an outdoor pool, and complimentary shuttle service to the New York City subway station, making it ideal for parents seeking comfort and convenience.

For a more rustic experience, consider Riverfront Inn Ossining, a boutique property with private river-view decks and vintage American décor. Both properties are situated in the safe, walkable downtown area, close to the Ossining Historical Museum and local parks—perfect for family-friendly exploration of this charming Hudson Valley town.

The heart of Downtown Ossining delivers the most authentic stay. Nestled along the Hudson River, this historic district offers easy access to landmarks like St. John's Church and the Ossining Historical Museum.

Stay at Old Town Hall Inn, a beautifully restored 1890s municipal building converted into a boutique hotel with Victorian architecture, original woodwork, and modern amenities. The area buzzes with weekend farmers’ markets and live music, offering a genuine taste of small-town American life. Its proximity to the Metro-North Railroad also makes commuting to New York City effortless—ideal for travelers who want culture, history, and connectivity all in one.

Yes, Hudson River Lodge is a standout eco-conscious B&B nestled along the Hudson River, built from repurposed warehouse materials and powered by solar energy. It emphasizes sustainability through rainwater harvesting and native landscaping.

Guests can join monthly local heritage workshops, such as river ecology tours, traditional woodworking, and craft fairs featuring regional artists. Each room displays art by local creators, celebrating Ossining’s unique Hudson Valley identity.

The lodge hosts a signature event: Starlight Nights by the River, where guests gather on the riverside deck to stargaze under dark skies—a perfect blend of nature, culture, and quiet reflection, ideal for mindful travelers.

Photographers should consider Old Bridge View Inn, which offers panoramic views of the Ossining Bridge across the Hudson River. Its location provides stunning golden-hour shots of bridge reflections and dramatic silhouettes at dusk.

The inn’s industrial-chic rooms feature large floor-to-ceiling windows and exposed brick walls, creating dynamic backdrops. Monthly urban photography workshops are hosted by professional photographers, covering composition, lighting, and night photography techniques.

Just a short walk away are St. John’s Church and the historic district, offering rich architectural details and candid community scenes—perfect for capturing the soul of a classic American riverside town.

Ossining offers excellent connectivity to New York City. Stay at Hyatt Place Ossining, which provides a free shuttle service to major subway stations like West 42nd Street, with a journey time of just 45 minutes.

Alternatively, the Ossining Train Station connects directly to Penn Station via Metro-North Railroad, taking only 35 minutes with frequent departures. Some luxury hotels, like Hudson River Boutique Inn, even offer private car transfers to Manhattan.

Whether for business or leisure, Ossining serves as a seamless gateway to NYC—combining rural charm with urban accessibility.

The Old Mill Inn stands out as a cultural gem. Housed in a former 19th-century flour mill, it preserves original stone walls and timber beams while hosting weekly events like Hudson River Story Nights, where elders share tales of immigration, river trade, and wartime history.

Guests can participate in hands-on workshops such as 19th-century breakfast-making classes, learning to prepare homemade bread and cured bacon using period recipes. The hotel also organizes guided tours to local artisan markets, showcasing handmade pottery, embroidery, and woodcraft by resident makers.

This deep integration of local heritage transforms each stay into a living history lesson—offering a rare glimpse into the authentic fabric of a Hudson Valley community.

Yes, Riverside Study Inn is a serene boutique option designed specifically for solo travelers. With only eight private suites, each room features a spacious desk, reading lamp, and soundproofing for maximum tranquility.

The inn offers free Wi-Fi, book lending services focused on American literature and Hudson Valley history, and a peaceful balcony overlooking the Hudson River. Daily morning coffee and healthy breakfasts are served in a quiet lounge setting.

Surrounded by walking trails and the nearby Ossining Library, it’s perfect for writers, digital nomads, or anyone seeking solitude. The owner, a former professor, hosts intimate book clubs—making it easy to connect with like-minded guests in a welcoming, low-pressure environment.

Yes, Hudson River Camping Cabins offers a full range of outdoor experiences. Guests can rent bicycles, paddleboards, and join guided river ecology tours along the Hudson River Greenway.

Try the Morning Riverside Walk, led by a naturalist, exploring birdwatching spots and seasonal flora. In summer, the Night Paddle Experience lets you glide silently under the stars, listening to local folklore narrated by guides.

Other hotels like Ossining Hilltop Lodge feature grassy lawns, fire pits, and meditation spaces. These activities promote wellness and deeper connection with the Hudson Valley ecosystem, making them ideal for nature lovers and active travelers.

Many Ossining hotels incorporate historical elements into their architecture and interiors. St. John's Heritage Inn, once a 1870s parish house, retains its Gothic arches, stained glass windows, and original church records displayed throughout.

Each room is named after a key figure in Ossining’s past—like the "Elizabeth Crane Suite" honoring a 19th-century educator. The hotel hosts regular Historic Town Walks, led by retired teachers, touring old post offices, railway ruins, and early factories.

The lobby features a hand-painted timeline mural depicting Ossining’s evolution from colonial settlement to modern town. This thoughtful storytelling turns every stay into a journey through America’s northeastern industrial heritage.

For couples seeking romance, Riverside Starlight Suite at Hudson River Boutique Inn offers a dreamy escape. Located on the top floor, it features a glass skylight dome and a private hot tub with river views—perfect for stargazing.

The hotel provides a Romance Package with champagne, artisanal chocolates, rose petals, and a custom photo frame. Guests can also book a private riverside dinner with live violin music and a four-course meal prepared by the chef.

Additionally, the host gifts a hand-written Ossining Love Map, highlighting secret walking paths and hidden viewpoints—ideal for anniversaries, proposals, or birthdays. This blend of intimacy and local charm makes it one of the most memorable romantic escapes near NYC.