Vacation rentals in Ossining

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Top-rated vacation rentals in Ossining

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A modern living room features a comfortable white sofa adorned with black and white patterned cushions. A coffee table sits at the center, surrounded by two sleek black chairs. A large wall-mounted TV and an abstract art piece enhance the room’s contemporary design.

Apartment in Croton-on-Hudson

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

4.79 out of 5 average rating, 138 reviews

Guest favorite

The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.

Home 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.

4.84 out of 5 average rating, 170 reviews

Guest favorite

A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.

Home in White Plains

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!

4.91 out of 5 average rating, 178 reviews

Superhost

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

4.81 out of 5 average rating, 136 reviews

Top guest favorite

A wooden deck is depicted, furnished with a round table and six chairs, an orange umbrella, and a grill. A hot tub is positioned nearby, and the surrounding greenery includes trees and manicured grass, with soft sunlight filtering through, creating a serene outdoor setting.

Home in Mount Kisco

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.

5.0 out of 5 average rating, 48 reviews

Top guest favorite

A spacious outdoor area features a modern pool surrounded by wooden decking. Lounge chairs are positioned under large umbrellas, providing shade. The two-story home is visible in the background, showcasing large windows that enhance natural light.

Home in Putnam Valley

Heated Pool, Ultra Modern Home 5B, hot tub, sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

4.98 out of 5 average rating, 177 reviews

Top guest favorite

A light yellow bicycle with a woven basket rests on a stone pathway beside a rustic stone wall. A potted plant filled with vibrant pink flowers decorates the entrance, which is framed by a white door that opens to a welcoming space.

Guest suite in Briarcliff Manor

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.

5.0 out of 5 average rating, 54 reviews

Top guest favorite

Home in Ossining

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

5.0 out of 5 average rating, 20 reviews

Guest favorite

A spacious living area features a light-colored sectional sofa adorned with a patterned throw and decorative pillows. Soft carpeting covers the floor, enhancing comfort. Natural light floods the space through large windows, illuminating the surrounding decor, including framed photographs on the walls.

Guest suite in Croton-on-Hudson

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.

4.93 out of 5 average rating, 175 reviews

Top guest favorite

A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.

Apartment in Ossining

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.

4.96 out of 5 average rating, 560 reviews

Top guest favorite

A spacious living area showcases a neutral color palette, complemented by a dark sofa and a decorative area rug. An air conditioning unit and wall art pieces add character, while natural light filters in through a large window. Red accent furniture enhances the inviting atmosphere.

Guest suite in Croton-on-Hudson

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.

4.91 out of 5 average rating, 65 reviews

Top guest favorite

A single-story home in a vibrant pink hue showcases a unique oval front door, flanked by dark shutters. A concrete pathway leads to the entrance, surrounded by a well-maintained green lawn and partial wooden fencing in the background.

Home in Peekskill

Charming Home in Peekskill NY

Enjoy this stylish home located less than a 10 minute drive from many walking/biking trails and tons of restaurants and local entertainment. It is also a 2 minute drive from the NY Presbyterian Hudson Valley Hospital perfect for Traveling Nurses and other short-term healthcare professionals. The neighborhood is quiet and situated at the end of a cul-de-sac, so there is no through traffic, suitable for walking your dog.

4.97 out of 5 average rating, 127 reviews