Vacation rentals in Orangeburg

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!

Well-Appointed & Cozy Studio w/ Parking & Wash/Dry

This well-appointed basement suite is designed for comfort and ease. Stretch out on the plush queen-size bed, unwind with your favorite shows on the smart TV, or enjoy a game night with the board games provided. The open layout includes a well-stocked full kitchen for simple meals , a sparkling clean bathroom, and a washer & dryer for guests to use. Just few steps from local deli, grocery shops, and restaurants. The place is perfect for solo travelers or couples looking for a comfortable stay.

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!

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.

The Hollow Inn at Sleepy Hollow

The Hollow Inn, a charming retreat nestled in the heart of historic Sleepy Hollow—just 45 minutes from NYC and a 15-minute stroll from the Tarrytown train station. Whether you're planning a festive fall getaway with a large family or a peaceful couples’ retreat, this cozy spot is the perfect home base. October is truly magical here, Sleepy Hollow comes alive with Halloween festivities, haunted hayrides, lantern-lit cemetery tours, and more. Book your stay and experience the legend for yourself!

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.

Hudson River Suite - Dobbs Ferry

Bright, modern 1BR in the heart of Dobbs Ferry on a quiet street—just 6 mins walk from the train to NYC (30 mins to Grand Central). Open-concept layout with river views, high-speed WiFi & separate bedroom with a work desk. Walk to the best cafes, restaurants, bars, riverfronts, shops and trails. Easy street parking right out front. Ideal for remote workers, couples, families and creatives seeking a stylish, peaceful stay with easy access to the city. Sleeps up to 4. No outdoor access.

Sweet & Cozy Home | Free parking

Public transportation just minutes away—bus steps from the home and train very close. Sweet & Cozy Home only 30 minutes from Manhattan. Welcome to your home away from home in Yonkers, NY. This two-floor apartment is perfect for families or groups, offering three comfortable bedrooms, a fully equipped kitchen, a cozy living room with Smart TV, and a private porch for morning coffee or evening relaxation. Easy commute to Manhattan, Bronx Zoo, Yankee Stadium, and other NYC attractions.

Hudson River Views | Private Balcony+ 2 Gyms

Wake up to stunning Hudson River views from this thoughtfully designed 1 bedroom apartment with a private balcony. Just a 10 minute walk to Metro North with Grand Central only 25 to 30 minutes away. Enjoy two fitness centers, a resort style pool, rooftop lounges, fast WiFi, and a fully equipped kitchen. Perfect for business trips, weekend getaways, or exploring NYC without staying in Manhattan. Staying for the FIFA Club World Cup Final? MetLife Stadium is only 30 minutes away.

Large New 4BR• Sleeps 13• Grand Central 30 mins

New York Gate is a bright, spacious, newly renovated 4-bedroom home on the NYC/Westchester border in Mount Vernon. Ideal for families & groups seeking the space of a whole home with fast direct access to New York City & the Hudson Valley. Grand Central is just 27–30 minutes away via Metro North. The perfect base for NYC sightseeing, sporting events, concerts, college visits and exploring the surrounding region. Free driveway parking. 241st Subway (2 train)-10 mins walk

Relaxing Family Retreat

Come relax with your family in this peaceful home. It’s a beautiful split family ranch with the top floor completely private to guests. En suite master bedroom boasts both a soaking tub and a standing shower. Located a 5-minute drive from the Palisades Center, a 5-minute drive from Rockland Lake State Park, and a 10-minute drive from the bustling downtown Nyack, you will find something for everyone in the family to enjoy. Or enjoy the deck, barbecue, and pool at home.

Modern 5BR 3 Full Bath, Fits 10 guests near NYC

Welcome to your home away from home! This newly furnished retreat features a brand-new kitchen, beautifully renovated bathrooms, modern furnishings, and bright, inviting spaces throughout. Enjoy the huge outdoor patio and fully equipped outdoor kitchen, perfect for relaxing or entertaining. Conveniently located near New York City and just 20 minutes from MetLife Stadium, it’s the perfect getaway for families, friends, and travelers seeking comfort and style.