House vacation rentals in Ossining

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Top-rated house rentals in Ossining

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Guest favorite

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.

Home in Rye

4.91 out of 5 average rating, 125 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!

Superhost

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.

Guest favorite

A formal dining area is highlighted by a large table surrounded by light grey upholstered chairs. A rustic stone fireplace adds warmth to the space, while a large mirror reflects natural light. Soft curtains frame the window, creating an inviting ambiance.

Home in White Plains

4.92 out of 5 average rating, 131 reviews

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!

Guest favorite

A spacious outdoor pool is surrounded by natural greenery, featuring a stone patio and a diving board. A covered lounge area with large windows overlooks the pool, providing a serene setting for relaxation and leisure.

Home in Stamford

4.95 out of 5 average rating, 258 reviews

Midcentury Modern ZenHouse Sculptor Studio

Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen

Top guest favorite

Home in Putnam Valley

4.98 out of 5 average rating, 126 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

Guest favorite

A bright entryway features light streaming in through the upper floor, illuminating the staircase. Two indoor plants, one on a shelf and another in a pot, add a touch of greenery to the modern decor. The light wooden flooring creates a warm atmosphere.

Home in White Plains

4.95 out of 5 average rating, 110 reviews

Cozy renovated 3bed White Plains Home

Visit beautiful Westchester County, New York and stay in this cozy home located in the vibrant city of White Plains. This newly renovated triplex is only a 12-min walk to North White Plains train station then a 45-minute train ride to Manhattan. Easy access to freeway I-287. Whole Foods, Target, Westchester Mall, and popular restaurants are all within 5 minutes’ drive. Perfect for small families, the space offers 3 bedrooms and 1 full bath across 3 floors with a multiple car parking backyard.

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, 107 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.

Guest favorite

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. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. 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.

Superhost

A tranquil outdoor deck features two yellow Adirondack chairs facing the Hudson River. The landscape includes distant mountains and a picturesque sunset casting warm colors across the sky, reflecting on the calm water.

Home in Peekskill

4.89 out of 5 average rating, 201 reviews

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 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, 192 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.

Guest favorite

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.

Home in Nyack

4.95 out of 5 average rating, 192 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.