Holiday rentals in Orangeburg

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Top-rated holiday rentals in Orangeburg

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.
Home in Highlands
4.93 out of 5 average rating, 134 reviews

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!

Top guest favourite
A modern living room features a gray sofa set against a wall adorned with a mountain landscape painting. A minimalist rug lies centrally on the floor, complemented by a white refrigerator positioned near an open doorway. Clean lines and neutral colors enhance the space.
Flat in White Plains
4.94 out of 5 average rating, 152 reviews

Clean, convenient, & close to train & downtown

Beautiful and clean one bedroom unit (with own bathroom, living room, fridge, and kitchenette-no stove) with easy off-street parking! Private entrance and easy walk to the White Plains Metro North Station! Great for those visiting NYC, working at nearby hospitals or companies, commuting into the city, or visiting family in Westchester! Living room sofa can become a futon to sleep on. We have toddlers, but we always try to keep any noise to a minimum, and they usually are in bed by 8 PM.

Guest favourite
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
4.97 out of 5 average rating, 63 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!

Superhost
A cozy living area features exposed brick walls and wooden flooring, furnished with a dark leather sofa adorned with red cushions. A glass coffee table sits in front, while a workspace with a desk and shelving units is visible, providing a functional yet inviting environment.
Flat in Nyack
4.88 out of 5 average rating, 67 reviews

The Main Event in Nyack!

"The Main Event" - Looking to stay in the heart of Nyack Village?This oversized loft space w/bedroom, extra large open apartment with kitchen,bathroom and living room with exposed brick walls,wide screen tv is awaiting! From windows you can see the Tappan Zee Bridge and Hudson River in the distance . Comfy lounge like living area on Main Street mixing it up with the locals, Farmer's Markets, Street Fairs and the lovely shops, eateries and culture abound. Public transportation. Private parking

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, 75 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...

Guest favourite
A sectional sofa with light-colored throw pillows is positioned beside a circular wooden coffee table. The table holds a decorative tray with a sunflower. A patterned area rug adds warmth to the seating area, complemented by a wall art piece featuring floral design.
Flat in Yonkers
4.95 out of 5 average rating, 104 reviews

The Harmony APARTMENT 30MINS TO NYC SLEEPS4.

FULLY EQUIPPED, NEWLY RENOVATED APARTMENT. LOCATED 3OMINS AWAY FROM THE CITY EITHER BY TRAIN OR CAR. FEEL RIGHT AT HOME WITH AMENITIES SUCH AS A FIRE PLACE, FULL KITCHEN WITH COOKING SUPPLIES , AND ALL BATHROOM AND BEDDING ESSENTIALS. WINDOWS IN ALL ROOMS AND BIKE TRAILS JUST STREPS AWAY, MAKE THIS A BRIGHT AND SERENE SPACE. Metro-North’s Harlem, Hudson and New Haven lines make for speedy service into Grand Central. Minutes away from both the Ridge Hill Mall and Saw Mill/Taconic parkways.

Guest favourite
A comfortable living room space features a dark blue sectional sofa with decorative pillows and an ottoman. A wooden coffee table with a decorative tray sits in front, and a stylish floor lamp provides soft lighting. A large wall art piece depicting a bridge is displayed.
Flat in Yonkers
4.94 out of 5 average rating, 263 reviews

Large, relaxing private 1 bedroom apartment.

Located on a quiet cul-de-sac, this self-catering 1 bedroom apartment with private driveway is located on the lower level of a private home and is perfect for anyone wishing to have a space to themselves. There is a roll-away single bed to accommodate a 3rd guest. We offer WiFi, Netflix and full cable TV access. Located near Executive Blvd and all the river towns. Plus, its only a short ride to all New York City has to offer. All reservation requests require verified Government ID.

Top guest favourite
A charming multi-level home is presented, featuring a stone facade complemented by classic dormer windows. The front yard has well-maintained landscaping and a walkway leading to the entrance. A spacious patio area is visible on the right, providing outdoor relaxation options.
Home in Hartsdale
5 out of 5 average rating, 30 reviews

Peaceful Palette: 35 mins to NYC

Nestled just 35 minutes from the heart of Manhattan, this cozy and chic 4 bed/3 bath home offers the perfect blend of comfort, style, and convenience. Whether you’re here to explore the city or relax in a serene, suburban retreat, our home is the ideal place to unwind. • 4 stylishly furnished bedrooms • Fully equipped kitchen • Comfortable, spacious basement lounge with pull out couch + kitchenette • Beautiful patio and balcony spaces • Extremely safe family centric neighborhood

Guest favourite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guest house in Pound Ridge
4.94 out of 5 average rating, 98 reviews

A Lovely Cottage in the Woods

Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

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
4.93 out of 5 average rating, 27 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!

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, 195 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!

Superhost
Guest suite in Dumont
4.82 out of 5 average rating, 289 reviews

Private ground level Studio Available.

This spacious and serene space has an attached garage. Street parking is allowed until October 15, 2025. You may also park in the attached garage as best you can. Up to you. Set the heat or AC, watch TV, nuke a meal, do some laundry, and there's a small office to gather your thoughts. There's high speed WI-FI and your own private entrance through your garage to come and go as you please.

Popular amenities for Orangeburg holiday rentals

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