Family-friendly vacation rentals in New Windsor

Apartment in Cornwall-on-Hudson

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.

4.93 out of 5 average rating, 122 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.

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.

4.87 out of 5 average rating, 211 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.

4.99 out of 5 average rating, 314 reviews

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 home in Wallkill

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.

Superhost

A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.

Loft in Cornwall

4.84 out of 5 average rating, 575 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

A spacious studio apartment showcases a wooden kitchen bar with stools, adjacent to an open area. A set of gym rings hangs centrally, adding a unique feature. Natural light fills the space, highlighting lush green plants and an organized laundry area with stacked appliances.

4.84 out of 5 average rating, 322 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Guest suite in New Windsor

The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.

4.96 out of 5 average rating, 241 reviews

Sunny Studio Peaceful Private Affordable + Goodies

Features -Two super comfy queen sized beds. -Heated Jacuzzi bathtub -Coffee/Tea Bar/Snacks -Home Baked Goodies on arrival -Safe. Secure. Private driveway. Parking at door. - Dedicated work desk. Wifi -Single traveler discount - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -35 min Bethel -Must be 25 years or older. No parties or gatherings. -2 guest maximum (inquire) -No 3rd party bookings -Overnight stay - not a hang out.

Home in Cornwall-on-Hudson

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.

4.92 out of 5 average rating, 171 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.

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.

4.93 out of 5 average rating, 471 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.

Home in Cornwall-on-Hudson

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.

4.87 out of 5 average rating, 135 reviews

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

This is a 2-story house-quiet residential street-safe town. Clean, eat-in kitchen, dining room, 2 twins, one queen, fold out bed in Living Room, shower/tub, washer/dryer, dedicated work area, Internet TV and ROKU 2nd floor, art supplies, large backyard, sml bbq, fire pit, games, kid-friendly. Free on/off-street parking. Close to Storm King, the Hudson, Woodbury Mall, West Point, hiking, restaurants, bars, malls. Town pool easy walking distance. No river or mountain view.

A modern kitchen area is depicted, featuring stainless steel appliances and granite countertops. An in-unit washer and dryer is positioned next to the refrigerator. Natural light enters through nearby windows, while a lofted sleeping area is visible above, separated by a sleek railing.

4.92 out of 5 average rating, 113 reviews

Airy Artsy Loft

Kick back and relax in this very spacious artist’s loft. There is one enclosed bedroom, one open loft space that serves as a second bedroom, and one full bath. This apartment features smart TV & High speed Fios WiFi, an in-unit laundry, and designer furnishings. Can accommodate 2-4 guests with one King bed and one Queen sized bed. Both are hybrid memory foam mattresses with natural cotton bedding for ultimate comfort and tranquility. One flights of stairs is required.

4.93 out of 5 average rating, 595 reviews

A staircase is depicted, featuring dark wooden steps and a polished handrail. Natural light enters through a nearby window, illuminating the neutral-colored walls. The staircase leads upward, accentuating the vintage charm of the home.

Guest suite in Newburgh

Glenbrook Country Villa

1856 high gothic revival brick country villa designed by architect Frederick C. Withers (Jefferson Market Library) in the hamlet of Balmville. Within the house is a cozy one bedroom second floor suite through a private side entrance and up a flight of stairs. Freshly updated with a mix of antique and contemporary furnishings against a backdrop of safe but stylish Farrow & Ball paint colors. Relax, enjoy complementary coffee and tea -- just make yourself at home.