Holiday rentals in Orangeburg

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Top-rated holiday rentals in Orangeburg

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Superhost
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
4.93 out of 5 average rating, 67 reviews

Waterfront Luxury in Town

Renovated, waterfront home minutes walking to all of downtown Piermont! Wonderful indoor & outdoor living. Tons of restaurants, bars & cafes walking & quick 15 minute drive to NYC train - the best of both! Huge master with King bed & 2 guest queen bedrooms. Loft space with 2 double beds, office and bonus hangout space. Open floor plan main living room, dining room & kitchen, over looking the Hudson River. Massive private outdoor space - 2 decks, patio & yard running right up to the water!

Top guest favourite
A stylish living area features a light-colored sofa with patterned cushions. Decorative wall plates and art are displayed above a sleek TV console. Two comfortable chairs, adorned with soft throws, invite relaxation, while a geometric area rug enhances the room's aesthetic.
Flat in Tarrytown
4.99 out of 5 average rating, 78 reviews

2 BRs, Easy Walking in Tarrytown and Sleepy Hollow

This special place, newly renovated and lovingly decorated, has a private entrance, off-street parking, and a washer/dryer. Close to everything the Sleepy Hollow/Tarrytown area offers - a short walk to both downtowns, the Metro North train to NYC, Hudson River parks, the Jazz Forum, the Tarrytown Music Hall, a Saturday farmers market. A mile walk to the incomparable Rockefeller Park Preserve, 1.5 miles to Kykuit, 2 miles to Lyndhurst. The list of attractions and destinations goes on and on...

Top guest favourite
Flat in Tomkins Cove
5 out of 5 average rating, 34 reviews

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Top guest favourite
A small flock of chickens is seen in a lush, green outdoor space surrounded by fencing. The chickens, displaying a variety of colors and patterns, roam on the ground among tall grass and scattered foliage. A branch is positioned in the background.
Guest house in Hastings-on-Hudson
4.91 out of 5 average rating, 899 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, never perfect private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (Rustic), yet tastefully curated with eclectic art and furnishings that can change depending on “finds.” Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking.

Guest favourite
A cozy seating area features a light blue sofa adorned with assorted cushions. Two round woven poufs serve as additional seating. A patterned area rug lies beneath, while a round dining table is visible in the background alongside a mirror and greenery.
Flat in Nyack
4.91 out of 5 average rating, 34 reviews

Bright Retreat in Nyack

Charming, Sunlit Apartment in the Heart of Nyack Nestled in the vibrant and scenic town of Nyack, this cozy yet bright apartment offers an inviting and tranquil retreat. Perfect for anyone seeking a peaceful, well-lit atmosphere, the apartment combines modern comfort with a cozy, intimate feel. Just steps from Nyack’s charming cafes, boutiques, and the stunning Hudson River views, this apartment is a perfect balance of cozy living and vibrant surroundings!

Top guest favourite
A modern studio apartment features a spacious bed with a low wooden frame and cozy bedding. A sofa bed is positioned nearby, surrounded by pillows. Natural light fills the room through two windows, with soft curtains framing the view. A decorative rug enhances the inviting atmosphere.
Guest suite in Tarrytown
4.93 out of 5 average rating, 265 reviews

Stylish Tarrytown Studio | Walk to Train & Main St

Modern designer studio 1 block from Main St, 8-min walk to Metro-North (35 mins to NYC). Private entrance, fast Wi-Fi, full kitchen, Queen bed + King sofa bed. Small front yard for a breath of fresh air. Walk to restaurants, cafes, and Hudson River parks. Ideal for couples, solo travelers, and remote workers. Explore charming Tarrytown, Sleepy Hollow, Rockefeller trails, and the Hudson Valley. A stylish, comfortable base for your next getaway!

Top guest favourite
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, 199 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 favourite
A cozy sleeping area features a spacious bed with a white quilted spread. Two bedside lamps provide soft lighting, and three windows allow natural light to brighten the room. The walls are painted in a calming light blue, complementing the carpet's subtle patterns.
Guest suite in Sleepy Hollow
4.97 out of 5 average rating, 63 reviews

Sleepy Hollow Private Apartment Airbnb

Beautiful studio apartment in Historic village of Sleepy Hollow. Walking distance to EF school & train to NYC (35 min ride). Hiking in next door Rockefeller Preserve & plenty of local restaurants. Great place for exploring the area made famous by writer Washington Irving. Includes smart TV & cable, computer workspace and kitchenette. 1 bed (queen size).

Top guest favourite
A light-filled living room features a comfortable sofa adorned with several cushions, providing a casual seating area. Two windows with patterned curtains invite natural light, while a decorative piece sits atop a classic cabinet in the background, adding character to the space.
Home in Dobbs Ferry
4.94 out of 5 average rating, 181 reviews

Beautiful Hudson River Bungalow in Dobbs Ferry

Serene and modern home. Newly renovated historic home on Main Street in the heart of the Village of Dobbs Ferry. Convenient to Manhattan and the Hudson Valley, the Old Croton Aqueduct trail is directly behind the home. This private apartment is on the second floor of a house with a separate entrance, offering complete privacy. Easy check-in with code.

Guest favourite
A bright living space is presented, featuring a dark sofa with patterned cushions and a round coffee table. A cozy armchair in warm tones is set nearby, with a potted plant in the corner. Natural light enters through a window, accentuating the soft area rug.
Flat in White Plains
5 out of 5 average rating, 14 reviews

Downtown Renovated Apartment with Parking

Renovated 3rd floor 1 bed/1bath apartment in dtown White Plains, walking distance to the train and City Center. One designated parking space. The apartment is on the 3rd floor, with a private entrance, kitchen and living room. The unit has access to laundry in the basement, which is shared with others. Please note that we have strict quiet hours!

Guest favourite
A studio apartment features a spacious bed covered with a navy bedspread, positioned against a colorful wall hanging. A cozy couch with a pink accent pillow sits nearby on a patterned area rug. Soft lighting contributes to a warm ambiance.
Flat in Piermont
5 out of 5 average rating, 9 reviews

A Gem in Piermont.

A private gem tucked away with wooded views and in the center of everything. Walk to the charming village or out to the end of the pier or to Tallman State Park. You enter this cozy studio apartment around the back and up the stairs over the garage. There is a balcony overlooking the hillside. Kick back and relax in this calm, stylish space.

Guest favourite
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
4.97 out of 5 average rating, 61 reviews

Idyllic & Chic in Piermont, 20 min from GW Bridge

Idyllic and charming home located in the Village of Piermont, a river town along the Hudson Valley, just 20 minutes from the George Washington bridge. Our home is right in town, set back from the main st yet steps away from the Bunbury coffee shop, restaurants, stores and a 5 min walk to the Hudson River and Tallman Park.

Popular amenities for Orangeburg holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Rockland County
  5. Orangeburg