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House vacation rentals in Ossining

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Top-rated house rentals in Ossining

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The spacious living area features large glass walls that provide serene views of the surrounding forest. A modern white sofa complements a wooden ceiling, while a quirky red chair adds a pop of color. Natural light floods the room, enhancing the warm wood tones throughout.

4.91 out of 5 average rating, 124 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

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

4.85 out of 5 average rating, 151 reviews

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.

A cozy living area features a large leather sofa adorned with soft, decorative pillows. A wooden coffee table is set with a small platter of snacks and a bottle of wine. A leafy indoor plant and bright natural light enhance the inviting space.

Home in White Plains

4.87 out of 5 average rating, 218 reviews

Bright&Comfy 2bed/1ba in quiet duplex

Bright, comfortable & quiet! Just outside downtown White Plains, this home has a relaxing living space with thoughtful touches. It offers easy accessibility to New York City (35 min Via Metro North) and Westchester (via highways and local buses). The house is set up for WFH, with great wifi via Verizon. It's an easy jump off spot for a fun weekend in Westchester. It comes with a dedicated parking spot, never worry about your vehicle! Bars, restaurants, shopping, groceries are all minutes away!

Top guest favorite

Home in Putnam Valley

4.99 out of 5 average rating, 123 reviews

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Top guest favorite

A modern full kitchen is equipped with stainless steel appliances, including a gas stove and fridge. A butcherblock table is positioned under natural light, with seating for two. The overall color scheme features gray cabinets and light wood flooring, enhancing functionality and style.

Home in Piermont

4.96 out of 5 average rating, 106 reviews

Piermont's Getaway Mt. Village Home. 30min to NYC

Nestled at the base of Tallman Mountain lies the quaint village of Piermont where a population of 2,500 sleep, live, thrive and enjoy life on the simpler side. Sip a coffee on the porch overlooking the Sparkill creek, take a stroll down Main Street for an array of options to visit. Fishing on the pier, dancing fireflies at night and wildlife throughout. A quick hike up the backyard mountain to the state park where you can enjoy a picnic and view of the Hudson while catching a glimpse of NYC.

A spacious living area features wooden beams overhead and large windows that provide ample natural light. A comfortable sectional couch is arranged around a coffee table, with a cozy armchair nearby. A stone fireplace adds warmth, while indoor plants enhance the inviting ambiance.

Home in Yorktown Heights

4.91 out of 5 average rating, 162 reviews

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms and a POOL. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook & seating area! Bedroom 1: King size bed & pack n play. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

Top guest favorite

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

4.99 out of 5 average rating, 106 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

Home in Cornwall

4.99 out of 5 average rating, 123 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Top guest favorite

A spacious living area is highlighted by exposed wooden beams and a stone fireplace. A cozy seating arrangement includes a colorful blanket draped over a large sofa. Natural light pours in from windows, illuminating a charming work desk and decorative artwork on the wall.

Home in Greenwood Lake

4.99 out of 5 average rating, 191 reviews

Spectacular Lake Views from Every Room & Garden

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features a seasonal waterfall cascading into a lily pond with fish and frogs. The shaded patio offers panoramic views and a gas grill. During the winter months, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy ambiance of our living room, with exposed wooden ceilings, a welcoming fireplace, a smart TV, a record player and board games.

A welcoming entryway is framed by a white picket fence, leading to a charming cottage. Lush greenery surrounds the path, which is composed of stone leading up to a blue front door. A trellis with climbing plants adds to the inviting exterior.

4.95 out of 5 average rating, 191 reviews

Chic Vintage Cottage in Artsy Village of Nyack

Chic, cozy and adorable, our recently renovated 1929 Nyack Village cottage is a one of a kind. Located one block from Main Street and the wonderful dining, shopping and culture downtown Nyack has to offer, our home is the perfect backdrop for a beautiful weekend retreat. Traveling for work? NYC is a quick 30 mile commute with fast access to public transportation. We welcome you to come and be our guests!

Top guest favorite

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

5 out of 5 average rating, 168 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Top guest favorite

A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.

Home in Livingston Manor

4.95 out of 5 average rating, 366 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek, gaze out XL windows, or cozy up by the fire—every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor—a quintessential Catskills town—and less than 2 hours from NYC.

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Popular amenities for Ossining house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

4.94 out of 5 average rating, 195 reviews

Private Hudson Valley Country Retreat

Top guest favorite

Home in New Paltz

4.98 out of 5 average rating, 503 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4.88 out of 5 average rating, 156 reviews

4Br Mountain Brook House on 130 acres w/ trails

An aerial view captures a stylish retreat surrounded by lush greenery. A wooden deck outlines a rectangular saltwater pool, accompanied by lounge chairs and large umbrellas. A shaded seating area is positioned nearby, promoting outdoor relaxation.

Home in Kerhonkson

4.92 out of 5 average rating, 129 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

Home in Litchfield

4.93 out of 5 average rating, 192 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

A charming carriage house features large windows and a high peaked roof, set amidst lush greenery. A well-maintained pool with a gentle fountain is situated in front, surrounded by landscaped gardens and inviting white lounge chairs.

Home in Englewood

4.94 out of 5 average rating, 166 reviews

Englewood NJ Country Carriage House (15 min NYC)

The spacious backyard features a well-maintained in-ground pool surrounded by lush green grass. Comfortable lounge chairs are positioned on the deck and by the pool. A slide is present for added fun, while the home is partially visible with an elevated deck overlooking the area.

4.92 out of 5 average rating, 143 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

An in-ground pool is situated amidst a lush green landscape, surrounded by tall grass and shrubs. The house, a charming two-story structure, is visible in the background, framed by gentle hills under a pastel sky. Outdoor seating and umbrellas are arranged nearby.

Home in Grahamsville

4.89 out of 5 average rating, 103 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

Weekly house rentals

A bright sitting area showcases a light pink custom sofa, complemented by an array of decorative shelves. Natural light enters through large windows, highlighting the wooden flooring. A ladder leads to the loft, and a cooler is positioned centrally on the floor, adding to the homey feel.

Home in Ossining

4.89 out of 5 average rating, 57 reviews

Camped Inn at Sundial Farm -- Tiny House

A two-story stone house is surrounded by lush greenery and wildflowers. The exterior features dark red window trim and a steeply pitched roof. Various plants frame the entrance, blending the structure harmoniously with the natural environment.

Home in Verbank

4.98 out of 5 average rating, 203 reviews

The Waterfall House

Top guest favorite

An open-concept living space features high wooden beam ceilings and a stone fireplace. Large windows provide ample natural light and scenic views of the lake. A staircase leads to an upper level, while a cozy seating area is arranged nearby, emphasizing relaxed living.

Home in Putnam Valley

5 out of 5 average rating, 21 reviews

Dr. Ruth’s Serene Lake Retreat

A single-story red brick house is framed by lush greenery and mature trees. A path leads to the front door, which features a wood frame and decorative glass. The yard is well-maintained, with manicured shrubs and a grassy area visible.

Home in Croton-on-Hudson

4.83 out of 5 average rating, 23 reviews

Croton Calm Retreat w/ hot tub

An inviting living area features dark wood paneled walls and a coffered ceiling. A soft, light-colored rug covers the floor, contrasting with a classic leather sofa. Large windows allow natural light to fill the space, with a holiday tree adding warmth to the corner.

Home in Ossining

4.85 out of 5 average rating, 41 reviews

Hudson Valley Escape

Top guest favorite

A stone patio is shown with six colorful chairs arranged around a fire pit. In the background, trees and a trampoline are visible, contributing to a serene outdoor setting, ideal for gathering and relaxation.

Home in Mohegan Lake

4.95 out of 5 average rating, 58 reviews

A nice place to getaway

A comfortable bedroom features a spacious bed with crisp white linens and a cozy green blanket. A plush armchair provides additional seating, while elegant light fixtures and floral wallpaper create a serene atmosphere. Natural light filters through the window, framed by dark curtains.

Home in Ossining

4.98 out of 5 average rating, 47 reviews

Nearaway - Midcentury Modern Cozy Cottage

The exterior of a charming gray house is presented, featuring multiple windows and a welcoming entrance. A well-maintained stone wall borders the property, leading to a set of stairs that ascend to the front yard, which is adorned with lush green grass and mature trees.

Home in Tarrytown

4.8 out of 5 average rating, 46 reviews

Lovely Tarrytown Home in Hudson

Private house rentals

Top guest favorite

The spacious patio features a table surrounded by chairs and several lounge seating options. A fire pit is positioned at the center. The sun can be seen rising in the background, casting warm light across the well-maintained yard and trees.

Home in Valhalla

5 out of 5 average rating, 17 reviews

Valhalla Home

Top guest favorite

An open living space features a Foster Leather sectional sofa positioned around a central coffee table. Natural light streams in from a large window, illuminating the wood-burning stove nearby. A cozy area rug adds texture to the floor, creating an inviting atmosphere.

Home in Gardiner

4.96 out of 5 average rating, 82 reviews

Mindful Escape: Theater, Trails, Wood Stove

Top guest favorite

A modern kitchen features sleek white cabinetry and stainless steel appliances, including an oven, microwave, and refrigerator. A double laundry unit is positioned beside the cooking area. Light reflects off the geometric backsplash, and natural light enters through a nearby window.

Home in Mamaroneck

5 out of 5 average rating, 28 reviews

Newly renovated modern private guest wing

Top guest favorite

Home in Far Hills

4.99 out of 5 average rating, 86 reviews

Pickle Farm

Top guest favorite

A comfortable living room features two soft armchairs positioned near a sleek marble coffee table. A large wall-mounted television is visible above a modern media console. Natural light enters through glass doors, leading to a deck with views of surrounding greenery.

Home in Redding

5 out of 5 average rating, 13 reviews

Cozy private retreat

Home in Greenwich

4.96 out of 5 average rating, 51 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Top guest favorite

An airy living space showcases large windows allowing natural light to fill the room. A cozy seating area is highlighted by a modern lounge chair and an indoor fireplace. A warm wood kitchen is visible in the foreground, emphasizing a welcoming atmosphere.

5 out of 5 average rating, 53 reviews

Moody Pond House: Weekend Country Escape

Top guest favorite

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

4.98 out of 5 average rating, 83 reviews

Waterfront Lake House

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