House vacation rentals in Ossining

4.9 out of 5 average rating, 112 reviews

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

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!

4.94 out of 5 average rating, 338 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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.

4.84 out of 5 average rating, 146 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.

4.99 out of 5 average rating, 159 reviews

A charming lakeside home with a red metal roof sits on a wooden deck overlooking the water. Surrounding landscaping features a serene pond, rocks, and green shrubs, creating a peaceful atmosphere. The setting sun casts a warm glow on the tranquil scene.

Home in Greenwood Lake

Lakefront Haven! Views, Beach, Firepit Free Kayaks

BOOKING FAST! Don't miss summer at the Lake! Escape to this beautiful 3BR home in Greenwood Lake! Experience the incredible lake views and our neighborhood beach to swim, launch kayaks, or fish, just steps away! You'll love the huge deck, cozy living area, firepit, ping-pong, free kayaks, paddleboard & well-equipped kitchen. Ideal for families or friends, this tranquil hideaway promises memories that will last a lifetime! Nearby wineries, breweries, restaurants, hiking, & more! 1 hour from NYC

4.92 out of 5 average rating, 120 reviews

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

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!

4.96 out of 5 average rating, 251 reviews

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

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

4.99 out of 5 average rating, 108 reviews

Home in Putnam Valley

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

4.86 out of 5 average rating, 142 reviews

The historic waterfront home is shown with a light yellow exterior and an A-frame roof. A welcoming porch with seating faces the river, framed by trees that add touches of color. The serene Hudson River is visible in the background under a clear blue sky.

Home in Nyack

Beautiful & Fun Waterfront Duplex on the Hudson

Enjoy a getaway to this charming historic waterfront home. Sip a glass of wine, a cup of Joe, or a refreshing cool drink from the 36 ft deck overlooking the Hudson River and Mario Cuomo Bridge beautifully lit up each evening. **PLEASE read everything in the description of "The Space" and "Other Things to Note" before booking. Thank you! Check out my "GUIDEBOOK" for my favorite picks including entertainment, shopping, eateries, and more. Non shedding pets welcome with additional fee $150.

4.91 out of 5 average rating, 155 reviews

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

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.

4.9 out of 5 average rating, 192 reviews

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

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.

4.99 out of 5 average rating, 185 reviews

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

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.

4.95 out of 5 average rating, 186 reviews

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

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!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Ossining house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 201 reviews

A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.

Home in Monroe

Garden Level Suite with Beautiful Pool

4.89 out of 5 average rating, 145 reviews

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

4Br Mountain Brook House on 130 acres w/ trails

4.92 out of 5 average rating, 245 reviews

A serene heated saltwater pool is framed by lush greenery, reflecting the sky above. A rustic wooden edge provides a natural transition between the pool and the surrounding landscape, which includes a prominent tree adding to the tranquil ambiance.

Home in Woodstock

Little owl Japanese teahouse: pool is OPEN

4.99 out of 5 average rating, 140 reviews

A private heated pool is surrounded by a wooden deck, featuring two red lounge chairs. Volleyball nets are set up across the pool, which is framed by lush greenery and a large umbrella providing shade. Clear blue water reflects the bright sky.

Home in Commack

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!

4.96 out of 5 average rating, 45 reviews

Home in Greenwich

Riverfront Cottage Retreat & Pool 35 mins from NYC

4.93 out of 5 average rating, 118 reviews

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

Modern Lux 5-Bed, Pool Open! Dogs Welcome

5 out of 5 average rating, 165 reviews

A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

4.94 out of 5 average rating, 158 reviews

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

Englewood NJ Country Carriage House (15 min NYC)

Show all

Weekly house rentals

4.75 out of 5 average rating, 16 reviews

A modern single-story home is set within a lush green landscape. A gravel driveway leads to the entrance, bordered by colorful landscaping and a small garden. Large windows offer natural light, while trees surround the property, creating a sense of privacy.

Home in Croton-on-Hudson

Secluded Mid-Century Modern Home

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.

4.89 out of 5 average rating, 56 reviews

Camped Inn at Sundial Farm -- Tiny House

4.87 out of 5 average rating, 78 reviews

A cozy living room is depicted with light-colored walls and wooden flooring. Two dark armchairs and a light sectional sofa surround a black coffee table. A vase of fresh tulips sits on the table, adding color. Large windows illuminate the space, showcasing a warm, inviting ambiance.

Home in Chappaqua

Chic and Cozy 2BD 1920's Cottage Retreat

4.86 out of 5 average rating, 21 reviews

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

Croton retreat w/ yard + 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.

4.89 out of 5 average rating, 35 reviews

Hudson Valley Escape

4.82 out of 5 average rating, 94 reviews

The exterior of a two-story house is highlighted at dusk, featuring warm light emanating from several windows. A neatly paved driveway is visible, bordered by low shrubbery and illuminated by subtle ground lighting. Nearby trees provide a natural backdrop.

Home in Piermont

Piermont View

4.95 out of 5 average rating, 57 reviews

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

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.

5 out of 5 average rating, 44 reviews

Nearaway - Midcentury Modern Cozy Cottage

Show all

Private house rentals

5 out of 5 average rating, 73 reviews

A sunlit sun room features large windows offering scenic lake views and a warm wooden ceiling. A cozy, circular seating area complements a central wooden table. Nearby, a dining table with black chairs sits atop a modern area rug, enriching the space's inviting ambiance.

Home in Vernon Township

Private Island + Lakefront Home

5 out of 5 average rating, 23 reviews

Home in Greenwood Lake

Lakeview House ~ Hot Tub, Firepit, Stunning Views

4.96 out of 5 average rating, 52 reviews

A modern living room is showcased with a large sectional sofa adorned with vibrant patterned cushions. A coffee table is positioned on a richly colored area rug. The walls are decorated with framed artwork, and natural light illuminates the space through two windows.

Home in Piermont

Idyllic & Chic in Piermont, 20 min from GW Bridge

5 out of 5 average rating, 10 reviews

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

Dr. Ruth’s Serene Lake Retreat

5 out of 5 average rating, 65 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

4.97 out of 5 average rating, 68 reviews

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

Waterfront Lake House

4.98 out of 5 average rating, 55 reviews

A light-filled living space features high ceilings and large windows that frame views of the waterfront. A comfortable sofa and an armchair are positioned around a rustic coffee table, while a dining area with dark wood seating overlooks the serene outdoor space.

Home in Piermont

Waterfront Luxury in Town