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 $85 CAD 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 and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of New Windsor vacation rentals include wifi 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 favourite
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, 157 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 favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 128 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Guest favourite
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, 104 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

Guest favourite
A stained glass window adorns the top of the image, displaying intricate patterns in soft colors. Below, a large window frames a serene view of the Hudson River, with a cargo ship gliding across the water. Mountains rise gently in the distance under a pastel sky.
Apartment in Newburgh
4.88 out of 5 average rating, 238 reviews

Riversong on Hudson - Private Full 2nd Floor

This 2nd floor sanctuary is not just a place to stay. Aside from the trains frequently passing nearby, Riversong is a pocket of peace, a window to breathtaking views, and a gateway to a historic city. In this light-filled abode, classic charm meets contemporary comfort. The living area, with a convenient, plush futon, offers space to relax or host an additional guest. Picture windows frame the outdoors, inviting you to gaze on the tranquil river and verdant tapestry of the landscape beyond.

Top guest favourite
A tiny house with large windows is nestled among the trees, offering a secluded retreat. A wooden deck with stairs leads to the entrance. An outdoor dining space with an umbrella and a propane grill is visible alongside a gravel area, complemented by a playful dog on the lawn.
Tiny homes in Wallkill
4.99 out of 5 average rating, 369 reviews

Get Away to "Hygge" Tiny House on 75 Private Acres

Escape to 75 acres of secluded, private land and lounge in this "hyggelig" tiny house. The house has everything you need, from heat and A/c, strong wifi, TV with streaming (sign in to Netflix, HBO, etc), full working kitchen (gas stove, oven, microwave), shower and bathroom. This tiny house has an incredible amount of light coming in from the very large windows throughout. Outdoor amenities include wood patio, propane bbq grill, dining table/chairs, fire pit. Lawn games available on request.

Top guest favourite
A rustic bench is positioned along a wooden fence, offering a vantage point of rolling hills adorned with autumn foliage. The scene captures a bright, open sky dotted with fluffy clouds, enhancing the natural beauty of the surrounding landscape.
Apartment in Marlboro Township
4.97 out of 5 average rating, 448 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Guest favourite
Apartment in Newburgh
4.89 out of 5 average rating, 267 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top guest favourite
A wooden porch leads to a vibrant purple door, framed by light-colored trim. Potted red flowers add color to the entrance, while natural light filters through the nearby trees, highlighting the rustic charm of the space.
Apartment in Cornwall-on-Hudson
4.98 out of 5 average rating, 243 reviews

Charming Efficiency

Newly refurbished efficiency apartment. Full kitchen, new appliances. Comfy space with queen bed and shower in bathroom. Short stroll to coffee bar & all of Cornwall! 3 miles to West Point. Ten minute drive to Storm King, Dia in Beacon, restaurants on the Hudson River. LOTS of hiking options, wine trails and exploring the Hudson Valley. Woodbury Commons is 10 miles for those who prefer shopping! Happy to help with dinner reservations & help to make your stay memorable! Pet friendly.

Guest favourite
Barn in Mountainville
4.95 out of 5 average rating, 160 reviews

Renovated Red 1890’s Hudson Valley Barn

Renovated barn in Mountainville, NY at the base of the Schunnemunk hiking trails. 1 mile from Storm King Art Center. 3 miles to Cornwall. 10 minutes from Woodbury Common Premium Outlet. 15 minutes to West Point. Private stairs & balcony leads to 500 square foot second-story space. You get the entire upstairs to yourself. The NYS Thruway does run between the house and the mountain. There is highway noise. TV has a ROKU. The WiFi signal is weak due to the metal siding on the barn.

Guest favourite
A charming two-story house is featured with a light yellow facade and white trim. A welcoming front porch with a bench overlooks the neatly landscaped yard, filled with greenery and flower beds. The inviting entrance is flanked by large windows and decorative shutters.
Home in Newburgh
4.88 out of 5 average rating, 144 reviews

Lady Montgomery

Enjoy our trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all that the Hudson Valley has to offer. Enjoy shopping, farms, hiking or dining. Equipped with an outdoor patio in season, fireplace, fire pit and 2 bikes. Everyone will enjoy their time in this comfortable artsy home!

Guest favourite
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, 156 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.

Guest favourite
A small dining area is positioned beneath a modern pendant light, featuring a round table surrounded by two tan chairs and a wooden chair. Sunlight filters through sheer curtains at the oversized windows, highlighting the warm wooden floor.
Apartment in Newburgh
4.93 out of 5 average rating, 222 reviews

Ela - a 1 Bed Escape, Washer/Dryer in Unit

Kick back and relax in this calm, stylish space. Located on the second floor of a historic Newburgh building, this apartment features scenic views from oversized windows, in-unit laundry, LED TV & Fios WiFi, and designer furnishings. Queen bed with Casper mattress. Two flights of stairs required. The neighborhood is quiet, with tree lined streets and historic mansions nearby, just 2 blocks always from the Hudson River waterfront.

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 house rentals in New Windsor have wifi?

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

  • Do apartment rentals in New Windsor have free parking?

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

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