Vacation rentals in New Windsor

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Quick stats about vacation rentals in New Windsor

  • Total vacation rentals

    Explore 40 vacation rentals in New Windsor

  • Nightly prices starting at

    New Windsor vacation rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 2,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of New Windsor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across New Windsor rentals

  • 4.8 Average rating

    New Windsor stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in New Windsor

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

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Top guest favorite
A bright bedroom features a spacious bed with crisp linens and a patterned rug. Two windows allow natural light to fill the room, complemented by neutral wall tones. A bedside table holds decorative items, and a potted plant adds a touch of greenery.
Apartment in Cornwall-on-Hudson
4.94 out of 5 average rating, 162 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

Top guest favorite
Apartment in Newburgh
4.96 out of 5 average rating, 27 reviews

Artist's Loft with Hudson River Views

A cozy spot to rest after a hike or while exploring the area. Your private retreat occupies its own unit on the top floor of our home, with full bathroom and kitchenette. You'll use a shared entrance and pass through shared space while coming and going. Once inside your unit, it's entirely self-contained and private. The open layout features a wall of windows framing spectacular views of the Hudson River. Wake up to sunrise over the river, and unwind to the sunset reflecting on the Beacon Hills.

Guest favorite
An aerial view captures a sprawling landscape at sunset. Lush green trees frame open fields, while a river snakes through the background. The sky is filled with warm hues of orange and yellow, creating a tranquil atmosphere over the countryside.
Farm stay in Salisbury Mills
4.87 out of 5 average rating, 109 reviews

Rustic Ranch w/ Fire Pit, Trails & Grazing Horses

Escape the city and wake to the sound of grazing horses. Nestled on a 50-acre equestrian property, the Carriage House blends cozy charm with eclectic design and wide-open skies. Sip morning coffee with views of the Moodna Viaduct, then hike our private trails or explore Storm King Art Center. Unwind by the fire pit, or book a hands-on horse experience with our gentle herd. Nearby: wineries, hiking, farm markets,& MetroNorth (NYC in ~90 mins) Ideal for couples, small families, or solo retreat

Top guest favorite
Home in New Windsor
5.0 out of 5 average rating, 105 reviews

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

Guest favorite
The exterior of a historic Gothic Victorian house displays a charming white façade with detailed gables and a covered front porch. Lush green lawns and trees surround the property, while a shaded outdoor seating area under a red umbrella adds to the inviting ambiance.
Home in Cornwall-on-Hudson
4.93 out of 5 average rating, 191 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

Top guest favorite
Home in Newburgh
5.0 out of 5 average rating, 22 reviews

River Views & Hot Tub | Riverview on Washington

A quiet escape above the Hudson River, Riverview on Washington is designed for slower mornings and unhurried evenings. The heated sunroom fills with soft eastern light, while spa-style baths and a private hot tub invite you to fully unwind. Walk to Liberty Street’s restaurants, galleries, and waterfront, then return to a calm, elevated home base that holds the steady pace you came here for. Close to town, but still a true retreat. Sleeps 4 across two bedrooms and two full baths.

Top guest favorite
A spacious living area is highlighted by a corner sectional sofa and a round marble coffee table. Soft, natural light filters through sheer white curtains, illuminating the warm wood floors. A dining space with a round table and modern chairs is visible in the background.
Apartment in Cornwall-on-Hudson
4.86 out of 5 average rating, 131 reviews

2-Bedroom in COH, near Newburgh & West Point

Two-bedroom apartment located right in the village of Cornwall-on-Hudson. Right next to the fantastic Italian Restaurante Peppitini and right across the street from the historic bandstand, if you're here on a Tuesday night in the summer, you'll likely be able to have a drink and catch a concert from the porch! Conveniently located close to West Point, Storm King Art Center, Newburgh, great hiking, and even Hudson River kayaking! The two bedrooms are roomy and each has a queen bed.

Guest favorite
A bedroom features a spacious bed with neutral-toned bedding and decorative pillows. A small bedside table holds a clock, while a light fixture hangs above. The room is brightened by natural light streaming through a window with blinds, contrasting with the warm wooden floor and white walls.
Apartment in Newburgh
4.92 out of 5 average rating, 524 reviews

Riverview Rowhouse, a vintage modern home

Stylishly renovated 1890 Rowhouse in Newburgh's up-and-coming Washington Heights District. Enjoy your morning coffee with views of the Hudson River and Mountains. Just 75 minutes from NYC, this home is a short drive to the Newburgh Waterfront and Liberty Street's hip new shops and restaurants such as Ms. Fairfax, The Flour Shop, Liberty Street Bistro, Mama Roux, The Newburgh Brewery, and more. Close proximity to the Beacon Ferry and a short drive to the Beacon train station.

Top guest favorite
Guest suite in New Windsor
4.93 out of 5 average rating, 40 reviews

A Cozy-Luxe Getaway | Scenic & Serene

The Nook is a thoughtfully designed upstate retreat, tucked in the heart of the Hudson Valley. It combines elevated design and natural simplicity: with tall ceilings, warm textures, and views of the distant mountains. The Nook is an intimate escape designed for rest, connection, and inspiration — the perfect getaway from the everyday hustle. It’s only 90-minutes from NYC and a short drive from the Hudson Valley’s best waterfronts, trails, wineries and dining experiences.

Top guest favorite
A serene lakeside view is captured at dusk, showcasing vibrant hues of orange and purple in the sky above a calm water surface. Silhouettes of trees and lanterns frame the scene, offering a peaceful ambiance as the last light fades.
Cottage in Newburgh
4.88 out of 5 average rating, 259 reviews

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

Guest favorite
A two-story house is situated on a quiet residential street, featuring a white exterior with a contrasting brick foundation. The entrance is framed by multiple windows, allowing natural light to illuminate the interior. A well-maintained yard with greenery surrounds the property.
Home in Cornwall-on-Hudson
4.86 out of 5 average rating, 161 reviews

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC

Clean 2-story house on a residential street/safe area Free on-off street parking Eat-in kitchen Dining room Living room-fold out ottoman Free washer-dryer in utility room 2 Internet TVs, WIFI Work area Large backyard, art supplies, games, books Fire pit Community Pool closed again. Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping No river or mountain view directly from house. Airbnb threw that in.

Top guest favorite
A charming blue house features a welcoming front porch with steps leading up to the entrance. White shutters adorn the windows, and flower boxes add color. A flag is displayed in front, with a well-maintained lawn and greenery surrounding the property.
Home in Cornwall-on-Hudson
4.96 out of 5 average rating, 141 reviews

Charming Hudson Valley Home: Minutes to West Point

Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

Popular amenities for New Windsor vacation rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in New Windsor?

    New Windsor has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in New Windsor?

    Experience the best of New Windsor with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in New Windsor?

    Four-legged friends are welcome in New Windsor. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in New Windsor?

    Yes! Work meets play with ease at over 20 vacation rentals in New Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in New Windsor have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in New Windsor have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in New Windsor have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in New Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in New Windsor have free parking?

    Absolutely! We offer over 10 house rentals with free parking in New Windsor. Enjoy a tailored experience with all the comforts you desire.