House vacation rentals in Orangetown

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!

Family · Location · Checkout

Piermont Getaway Mt. Village Home. 30 min to NYC

Nestled at the base of Tallman Mountain lies the quaint village of Piermont where a population of 2,500 sleep, live & thrive enjoying life on the simpler side. Sip coffee on the porch overlooking the Sparkill creek. Stroll down Main Street to visit an array shops/restaurants. Fishing on the pier, dancing fireflies at night and wildlife throughout. A quick hike along the firetrail to the state park will overlook the backyard mountain, a view of the Hudson & catching a glimpse of NYC or a picnic.

Family · Value · Hiking

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!

Location · Value · Hospitality

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.

Value · Family · Air conditioning

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.

Location · Value · Hospitality

Entire 4BR House, Walk to Train! Yard + Parking

Enjoy the 4BR/2BA house to yourself in one of Westchester’s most family-friendly communities, <40 min from NYC. Ideal for families (dog friendly, 1 per stay), relocations and longer stays, with a fenced yard, parking, fast Wi-Fi, washer/dryer and kid essentials (a crib, bassinet & more). Walk to Metro-North (13 min), stores, restaurants and Mamaroneck Ave. Kids will love the fenced yard and Florence Park down the block, with a playground, basketball and tennis. Need a longer stay? Ask us!

Family · Location · Nearby

Spacious NYC Getaway | Sleeps 10 | Parking

Stay just outside Manhattan in this modern 4BR home designed for groups and families who want space, comfort, and easy access to NYC. Sleeps up to 10 comfortably (6 beds across 4 bedrooms) 4 bedrooms + 3.5 bathrooms Open-plan kitchen & dining – perfect for gathering Free driveway and street parking Washer & dryer Located a short walk from McLean Avenue’s lively restaurants and bars. Getting to NYC is simple: Quick Uber ride to the subway or Metro-North 30 minutes to Midtown Manhattan

Family · Value · Comfort

Backyard Gazebo in Quiet NYC Suburban Stay

Welcome to our private split-level home with a fenced-in backyard! Enjoy this entire single-family home and never walk more than 8 steps between levels! This is a year-round perfect spot - enjoy the outdoor patio and indoor electric fireplace during your short term or midterm stay. We are located in Westchester County, just outside NYC. The house is 1.5 mi from 3 Metro-North stops and a 30-minute ride to Manhattan. Send us a message and we will let you know how far it is to your event.

Value · Family · Condition

Beautiful Hudson River Bungalow in Dobbs Ferry

Serene, modern apartment in a beautifully renovated historic home on Main Street in the heart of Dobbs Ferry. Located just minutes from the train to Manhattan and surrounded by the beauty of the Hudson Valley, this private second-floor apartment offers a separate entrance and complete privacy. The scenic Old Croton Aqueduct Trail runs directly behind the property, perfect for walking, running, and biking. Easy self check-in. Ideal for business travelers, couples, and extended stays.

Family · Location · Heating

2026 World Cup! Beautiful Colonial Near MetLife

• Only 6 miles and 10 minutes to MetLife Stadium — 2026 FIFA World Cup venue! • Ten miles from the heart of NYC • Six miles to American Dream Mall • 45 minutes to Hudson Valley, Angry Orchard, and City Winery • 45 minutes to the Poconos, the NJ Shore, and Woodbury Commons • 90 minutes to the Hamptons • Endless dining options within walking distance • Whole Foods, ShopRite, Aldi, and Target all within one mile • Every major retailer within five miles

Family · Location · Walkability

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225

Family · Value · Accuracy

Spacious, bright 5 bedroom house near West Point

Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Location · Value · Getting around