House vacation rentals in Ossining

4.91 out of 5 average rating, 117 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!

4.84 out of 5 average rating, 148 reviews

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.

4.86 out of 5 average rating, 213 reviews

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

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!

4.95 out of 5 average rating, 102 reviews

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

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.

4.96 out of 5 average rating, 103 reviews

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

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.

5 out of 5 average rating, 277 reviews

The entrance of the cottage is framed by lush greenery and vibrant foliage. A stone pathway leads to a welcoming front door, accentuated by an overhanging roof and outdoor lighting. The architectural details are complemented by the surrounding natural landscape.

Home in Kerhonkson

Cook House | Modern Cottage w/ Hot Tub & Fireplace

Featured in Vogue, Curbed, and Remodelista, Cook House is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature. Hosted by The Reset Club, a member of 1% for the Planet.

4.91 out of 5 average rating, 157 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.

4.98 out of 5 average rating, 165 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 Sterling Forest

Beautiful Lakefront Haven! Beach, Views, Kayaks!

Experience summer at the Lake! Escape to this beautiful 3BR home in Greenwood Lake with incredible lake and mountain views. Enjoy our neighborhood beach to swim, free kayaks, and paddle board, or fish, just steps away! You'll love the huge deck, cozy living area, firepit, ping-pong, & well-equipped kitchen. Ideal for families and friends, this tranquil hideaway promises memories that will last a lifetime! Nearby boat marinas, wineries, breweries, restaurants, hiking, & more! 1 hour from NYC

4.89 out of 5 average rating, 197 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, 187 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 Sterling Forest

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.

4.94 out of 5 average rating, 159 reviews

An inviting open living space features large glass sliding doors that provide a view of the water. Natural wood accents complement the light-colored furniture, including a spacious sofa and a comfortable armchair, while a wooden coffee table sits centered on a soft area rug.

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC"! Welcome to Long Island's Gold Coast! Enjoy stunning beachfront views from this charming home. You may spot the bald eagle family that lives around the corner! Local spots to visit include the Vanderbilt Mansion and Planetarium, Caumsett State Park Preserve, Del Vino Vineyards, Paramount Theatre, Downtown Huntington, Northport Main Street shops and restaurants, and more!

4.95 out of 5 average rating, 189 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

4.94 out of 5 average rating, 189 reviews

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

Private Hudson Valley Country Retreat

4.98 out of 5 average rating, 497 reviews

Home in New Paltz

midcentury mod * HOT TUB * walk out trail 2 mohonk

4.92 out of 5 average rating, 114 reviews

An aerial view of a house is surrounded by dense green trees, with a clear pool visible in the backyard. The lawn is lush and includes a pathway leading to the pool area, blending harmoniously with the natural landscape.

Home in Warwick

Summer Retreat! Amazing Pool, Playground, 7 acres!

4.86 out of 5 average rating, 165 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

4.99 out of 5 average rating, 145 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!

4.93 out of 5 average rating, 123 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

4.94 out of 5 average rating, 164 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)

4.92 out of 5 average rating, 139 reviews

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.

Home in Beacon

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

Show all

Weekly house rentals

5 out of 5 average rating, 74 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 Highland Lake

Private Island + Lakefront Home

5 out of 5 average rating, 15 reviews

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

Valhalla Home

4.78 out of 5 average rating, 18 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

4.89 out of 5 average rating, 56 reviews

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

Camped Inn at Sundial Farm -- Tiny House

5 out of 5 average rating, 15 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

4.82 out of 5 average rating, 22 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

4.85 out of 5 average rating, 39 reviews

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

Hudson Valley Escape

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

Show all

Private house rentals

5 out of 5 average rating, 4 reviews

An inviting living area showcases a cozy green sofa and two light-colored armchairs, emphasizing a natural wood coffee table. A rustic stone fireplace adds warmth, with a well-equipped kitchen visible in the background, featuring a gray island with seating and stainless steel appliances.

Home in Brookfield

3.5 Acres of Relaxation, Pool, & Cozy Charm

5 out of 5 average rating, 31 reviews

A modern cabin features a dark wooden exterior and large glass windows allowing natural light to fill the interior. A welcoming deck is furnished with chairs, surrounded by lush greenery and mature trees, creating a peaceful and inviting outdoor space.

Home in Pleasant Valley

The Wildflower House

4.86 out of 5 average rating, 79 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

5 out of 5 average rating, 23 reviews

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

Newly renovated modern private guest wing

5 out of 5 average rating, 30 reviews

Home in Greenwood Lake

Lakeview House ~ Hot Tub, Firepit, Stunning Views

5 out of 5 average rating, 87 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

4.97 out of 5 average rating, 75 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