Vacation rentals in Ossining

4.95 out of 5 average rating, 135 reviews

A modern coffee station is featured on a bright countertop. A sleek Keurig coffee maker sits beside a stainless steel kettle. Two canisters, labeled 'coffee' and 'tea', are presented with wooden lids, adding a touch of warmth to the kitchen space.

Apartment in Ossining

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

4.8 out of 5 average rating, 168 reviews

A private patio area is highlighted with comfortable seating arranged around a coffee table. A barbecue grill is positioned nearby. Soft lighting is strung overhead, enhancing the cozy atmosphere. Steps lead to a landscaped area with greenery, creating an inviting outdoor space.

Apartment in Peekskill

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

4.88 out of 5 average rating, 34 reviews

A lush garden scene captures a scenic view of the Hudson River at sunset. Vibrant greenery frames the picturesque landscape, and the soft light reflects on the water, enhancing the tranquility of the surroundings. Various plants and flowers add color to the serene outdoor space.

Home in Ossining

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.

Guest suite in Croton-on-Hudson

A spacious living area is presented with a light-colored sofa set and a wooden dining table surrounded by chairs. Large windows fill the room with natural light, complementing the neutral decor and flooring. A media unit is positioned against the wall, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 134 reviews

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: Drive, walkway and entrance accessible to full size wheelchair (see photos) however the bathroom is not accessible to a wheelchair. Guest must have ability to enter and maneuver the bathroom on thier own.

4.9 out of 5 average rating, 190 reviews

A modern kitchen area is highlighted by a central island with a sink and a wooden cutting board, accompanied by two glasses. Well-placed pendant lights illuminate the space, while expansive windows provide views of the Hudson River and surrounding greenery.

Home in Peekskill

The Peekskill RiverView House

The Peekskill RiverView House A fully renovated dream house overlooking the historic Peekskill Bay. This 3 bedroom 3.5 bath designer house is a 5 minute walk to the train station as well as the historic downtown. It’s truly the gateway to the Hudson Valley along with having the walkable access to culture, hiking, biking, culinary, spa, and entertainment activities within City limits. Expansive decks on all 3 floors with spectacular Hudson River views from every room.

Guest suite in Pleasantville

Two cookbooks are positioned on a countertop. The left book features a rustic basket illustration with the title 'sunny days.' The right book, titled 'The Painted Garden Cookbook,' displays a colorful illustration of various vegetables and herbs, suggesting an emphasis on homegrown recipes.

4.83 out of 5 average rating, 72 reviews

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!

4.99 out of 5 average rating, 311 reviews

Treehouse in Wallkill

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

4.92 out of 5 average rating, 253 reviews

A rooftop viewing deck is illuminated by soft lighting, featuring sleek benches positioned along the edge. The serene water view reflects the evening sky, with distant lights twinkling across the horizon. A modern architectural structure frames the scene, enhancing the outdoor experience.

Guest suite in Tarrytown

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!

4.83 out of 5 average rating, 127 reviews

A pair of sliding glass doors, framed in white, opens to a softly lit bedroom area. The spacious bed is centered against a neutral wall, with bedside lamps placed on either side. A textured area rug adds warmth to the wooden floor.

Apartment in Nyack

Nyack Retreat

This stylish apartment is tucked away but right in the center of the popular town of Nyack. Very comfortable and spacious, perfect for an amazing get away. Please note: This is a quiet multi-family home that houses four apartments. We do not allow any parties or gatherings. Please do not book this place if you plan to host an event. Only persons booked are allowed without permission. Thank you respectfully.

4.64 out of 5 average rating, 75 reviews

A stone pathway leads to a white front door, framed by large windows. A small light fixture hangs above the entrance. Potted plants and bicycles are situated near the door, contributing to a welcoming atmosphere. Sunlight casts gentle shadows on the surfaces.

Apartment in Ossining

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.

4.91 out of 5 average rating, 204 reviews

A calm waterfront scene is captured with soft mist hovering over the tranquil water. Vivid autumn foliage is visible on the distant shoreline, providing a serene backdrop to the stillness of the lake and creating a peaceful ambiance.

Cottage in Mohegan Lake

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.

4.91 out of 5 average rating, 579 reviews

A spacious living area features a cozy seating arrangement with a soft white couch and a round wooden table. Sunlight filters through large windows, offering views of the lush greenery outside. A desk with a computer adds a functional workspace, complementing the rustic wooden decor.

Barn in Mount Kisco

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

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Popular amenities for Ossining vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Ossining

5 out of 5 average rating, 14 reviews

A modern kitchen features navy blue cabinetry with glass-fronted upper shelves. A marble countertop provides a functional space, complemented by an under-counter refrigerator and small appliance area. Stylish bar stools are positioned at a nearby counter, enhancing the kitchen's usability.

Home in Valhalla

Valhalla Home

BethRating, 5 stars1 week ago

This is an outstanding house and Ben is an excellent host. I would stay here again in a heartbeat and would recommend to anyone looking for a quiet, comfortable place to stay in Westchester.

A two-story blue house features a front porch with white railings and steps leading to the main entrance. Large windows provide ample natural light. A fence encircles the front yard, while greenery and flower beds enhance the outdoor space. Nearby trees contribute to the inviting exterior.

Apartment in Yonkers

4.83 out of 5 average rating, 12 reviews

The Hide at Hudson-35 min to NYC

TheodoreRating, 5 stars2 days ago

Thank you for allowing me to stay at your house. This location is 30 mins away from time square. This is great for like minded folks who wouldn’t mind driving to the city. Instead of paying expensive hotel rates that only gets you 1-400 sf rooms. This place is a basement apartment. And indeed spacious for the attendees allowed.

4.99 out of 5 average rating, 89 reviews

Cabin in Sterling Forest

Modern Nordic Designed Cabin

FeRating, 5 stars6 days ago

The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!

5 out of 5 average rating, 17 reviews

Two blue camping chairs are positioned around a fire pit, surrounded by a ring of stones. Lush green trees create a natural backdrop, allowing sunlight to filter through the foliage. A trail leading into the wooded area is visible in the background.

Yurt in Ossining

Private Glamping Oasis

YasminRating, 5 stars2 weeks ago

very comfortable and quiet. It's cold at night, so you need a heater, but after that, everything is very good

Guest suite in Briarcliff Manor

5 out of 5 average rating, 39 reviews

Enjoy Summer Living "Stone Haven" Hudson Valley

PatriciaRating, 5 stars3 months ago

What a beautiful stay! The place was private, quiet, cozy and clean. We felt so welcomed by our host with special treats left behind, including snacks, juice and milk. The place was so clean and comfortable. Maria went above and beyond to help make our stay so amazing. She was so generous and kind, we were blessed. Hope to be back in the summer. Lots to do in close proximity including hiking and great restaurants. Thank you for sharing your lovely home with us.

4.95 out of 5 average rating, 57 reviews

A modern bathroom features a glass-enclosed shower and a white toilet. The grey tiled walls complement the dark wood cabinetry. Natural light enters through a window with sheer curtains, and a small plant adds a touch of greenery to the space.

Home in Mohegan Lake

A nice place to getaway

LizRating, 5 stars1 month ago

We’ve stayed at Filiz’s place a few times and it’s perfect! Quiet, clean, and easy to get to where we needed to be. We’ll be back!