Holiday rentals in Orangetown

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Top-rated holiday rentals in Orangetown

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

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Superhost
Home in Ossining
4.85 out of 5 average rating, 161 reviews

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.

Top guest favourite
Flat in Tarrytown
4.99 out of 5 average rating, 91 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 light and airy kitchenette features a spacious countertop and ample natural light from a large window. Cabinets are neatly organized along one wall, showcasing a wine rack and various kitchen essentials. A decorative plant adds a touch of greenery to the inviting space.
Flat in Nyack
4.89 out of 5 average rating, 85 reviews

Home Away From Home

The best of both worlds just 32 miles north of New York City: a cozy studio apartment steps away from bustling downtown Nyack. The studio features a comfortable queen-sized bed, a kitchenette, and a modern bathroom with a shower. Enjoy bars, restaurants, antique shops, specialty stores, and boutiques all within less than a five minute walk. The Hudson River and Nyack Beach State Park are also just a short distance away, making it easy to enjoy all the outdoor activities the area has to offer.

Top guest favourite
Home in Piermont
4.97 out of 5 average rating, 122 reviews

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.

Guest favourite
A spacious deck is shown overlooking the Hudson River, featuring a decorative rug and a small table with chairs. An umbrella provides shade, and lush greenery is visible in the background, enhancing the serene riverfront view.
Home in Nyack
4.87 out of 5 average rating, 156 reviews

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.

Top guest favourite
Cabin in Sterling Forest
4.96 out of 5 average rating, 478 reviews

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Guest favourite
Cottage in Sterling Forest
4.98 out of 5 average rating, 382 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

Top guest favourite
A shaded gazebo features a comfortable eight-seat patio lounge set arranged around a fire table. The surrounding area is well-maintained grass, providing a spacious setting for outdoor relaxation.
Home in Mount Vernon
4.97 out of 5 average rating, 119 reviews

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.

Top guest favourite
A serene outdoor space is depicted, featuring several adirondack chairs and a small fire pit surrounded by green grass. The setting sun casts a warm glow over the landscape, with views of the Hudson River and a two-story house in the background.
Flat in Ossining
4.96 out of 5 average rating, 534 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.

Guest favourite
A tree-lined street is depicted, leading towards the Hudson River, visible in the distance. Residential buildings line both sides, with vehicles parked along the curb. Greenery enhances the scene, contributing to a serene atmosphere, while the rolling hills rise beyond the river.
Flat in Hastings-on-Hudson
4.85 out of 5 average rating, 334 reviews

Entire 2 Bedroom apt, Hastings-On-Hudson near NYC

This brand new two-bedroom apartment is perfect for experiencing the beauty of the Hudson Valley while being a 5-10 min walk away from the Metro North station (45 min ride to Grand Central). It is very close to the heart of downtown that is filled with locally well-known restaurants, coffee shops, and a farmers market. This apartment includes a spacious backyard, perfect to enjoy breakfast with your family or group of friends with a view of the Hudson River.

Superhost
Guest suite in Dumont
4.82 out of 5 average rating, 324 reviews

Private ground level Studio Available.

This spacious and serene space has an attached garage. Street parking and overnight street parking is allowed until October 15, 2026. 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.

Top guest favourite
Cottage in Sterling Forest
5 out of 5 average rating, 36 reviews

"Wake Up to Nature | Lake View + Beach Access"

Welcome to The Cozy Cove, where rustic charm meets modern comfort. Just one hour from NYC. In the summertime, you're perfectly situated to enjoy swimming, kayaking, paddleboarding, boating, fishing, and hiking nearby trails. And you're just a short 5-minute walk to the private beach and lakefront community access.

Popular amenities for Orangetown holiday rentals

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