Family-friendly holiday rentals in New Windsor

Flat 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, 138 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.

4.83 out of 5 average rating, 177 reviews

A spacious living area features a black leather sofa and an orange ottoman, complemented by a large potted palm. Bright light enters through the open door, enhancing the warm wood flooring and inviting atmosphere.

Flat in Newburgh

Historic Stunner w/WasherDryer, Balcony, 2 bedroom

Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!

4.99 out of 5 average rating, 333 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.

4.84 out of 5 average rating, 605 reviews

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 Mountainville

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.

4.97 out of 5 average rating, 331 reviews

A cozy room with a small kitchenette and a dining area featuring a round table and two chairs. Natural light fills the space through a glass door, which leads to the side yard. A minimalist wall art piece adds a touch of character to the room.

Guest suite in Beacon

Hiker's nest

This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

Guest suite in Marlboro Township

A spacious bedroom features a large queen bed with a contrasting striped blanket. Nightstands are positioned on either side, and a lamp provides soft lighting. Two windows with light-filtering curtains allow natural light to fill the room, complemented by a beige carpet.

4.96 out of 5 average rating, 507 reviews

Spacious & Private Hudson Valley Getaway

Welcome to Marlboro! This private space in our home features a private entrance, private bathroom with a nice standing shower, eating area (not a kitchen) with tea kettle and coffee machine, toaster, microwave and refrigerator with freezer. There is a table and chairs, love seat couch that transforms into a small cot, queen bed, walk in closet and 55 inch smart TV with a full motion TV stand. We are permitted to operate in the town of Marlboro and a yearly fire inspection is conducted.

4.85 out of 5 average rating, 117 reviews

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

Lady Montgomery

Enjoy this 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 like shopping, hiking or dining. Equipped with an outdoor patio, fireplace, fire pit and 2 bikes to help you explore. Everyone will enjoy their time in this comfortable artistic home!

4.92 out of 5 average rating, 484 reviews

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.

Flat in Newburgh

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.

Guest house in Cold Spring

A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.

4.99 out of 5 average rating, 196 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

4.88 out of 5 average rating, 234 reviews

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

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

4.89 out of 5 average rating, 385 reviews

The studio apartment is furnished with a Queen size bed dressed in neutral bedding, complemented by a cozy reclining chair. Brick walls and wooden accents create a warm environment. A small television is positioned for viewing, and a kitchenette area is visible in the corner.

Guest suite in Beacon

Cozy retreat, centrally located in Beacon NY

Private studio apartment for single person or couple (3rd guest can sleep on sofa). It is walking distance to Metro-North and Main St. Beacon. Private entrance on the right-side of the house. Queen bed with mini-fridge and microwave (no kitchen, no cleaning fee!). A quiet homebase to explore all the Hudson Valley has to offer. **Winter Advisory ** I will refund 100% if you chose to cancel your reservation due to a forecasted snow event within 24hrs of arrival

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.

4.95 out of 5 average rating, 258 reviews

The Loft at 12 Clara- Serene-Private-Welcoming

Features - Large space 12 ' ceilings with fans +AC - Exceptional quality in a homey atmosphere - 2 Super comfy queen sized beds. - Huge bathroom - Heated Jacuzzi bathtub - Seated shower - Coffees, teas, morning muffins - Private driveway. Parking at door. - Writing desk. - Wifi - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -Must be 25 years or older to book. No parties. - dbl occ

Popular amenities for New Windsor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.91 out of 5 average rating, 256 reviews

The log cabin is set amidst lush greenery and trees, featuring a sloped lawn that leads to the entrance. Solar panels adorn the roof, while diverse plant life and landscaping surround the home, creating a harmonious blend with nature.

Flat in Philipstown

Foxglove Farm

4.96 out of 5 average rating, 362 reviews

A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

4.98 out of 5 average rating, 133 reviews

A cozy bedroom features a metal four-poster bed with crisp white bedding and decorative pillows. A woven basket rests on a wooden bench at the foot of the bed. Soft lighting is provided by two bedside lamps, with calming blue walls that enhance the serene atmosphere.

Guest suite in Gardiner

Cozy Studio at Yoga Center + Hot Tub + Mtn Views

4.87 out of 5 average rating, 134 reviews

A bright living room features high ceilings and large windows, providing natural light and views of the surrounding trees. Stylish designer furniture, including two armchairs and a dark sofa, complements a geometric artwork on the wall. A textured area rug enhances the space.

Home in Wallkill

Modern Upstate Gem Surrounded by Trees | Hot Tub

4.83 out of 5 average rating, 110 reviews

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

Home in Newburgh

Entire Home (private pool), Event Friendly

4.99 out of 5 average rating, 169 reviews

The cabin is positioned in a wooded area, featuring a dark exterior and a sloped roof. A spacious patio area is visible, equipped with seating and a fire pit. A hot tub is placed nearby, illuminated by soft lighting along the pathways.

Cabin in Ellenville

Catskills Cabin, Hot Tub, Wood Stove, King Bed

4.95 out of 5 average rating, 410 reviews

The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.

Guest house in Beacon

Cozy Mountainside Suite - Minutes from Beacon

4.95 out of 5 average rating, 153 reviews

A serene cabin is nestled among trees, overlooking a private pond. The exterior features a mix of corrugated metal and wood, blending harmoniously with the natural surroundings. A spacious outdoor area includes a fire pit and seating, offering a tranquil retreat.

Cabin in Mountain Dale

Private lake cabin w/hot tub, views and fruit

Family- and pet-friendly home rentals

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.

4.93 out of 5 average rating, 178 reviews

Cozy Riverfront Victorian in the Hudson Valley

4.99 out of 5 average rating, 205 reviews

A well-appointed room features a queen-sized bed with crisp white linens and a patterned throw. Natural light filters through multiple windows, illuminating a vintage bar cart and a small black mini-fridge. A wooden dresser and a chair complement the inviting space.

Flat in Beacon

Stylish Private Studio 1 block from Main St Beacon

4.93 out of 5 average rating, 613 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

4.99 out of 5 average rating, 180 reviews

A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.

Home in Newburgh

Balmville Mid-Century Gem & Work From Home Retreat

4.96 out of 5 average rating, 269 reviews

A charming two-story house features warm wooden siding and multiple red window accents. A welcoming front porch is adorned with lights, complemented by a gently sloped pathway leading up to the entrance, surrounded by lush greenery and seasonal foliage.

Home in New Paltz

Eclectic one-bedroom house

4.78 out of 5 average rating, 648 reviews

The exterior of a historic stone farmhouse is shown, featuring a vine-covered wall and landscaped garden. Steps lead to the entrance, surrounded by greenery and floral elements, with large windows allowing natural light. The serene outdoor setting reflects the charm of the surrounding countryside.

Flat in High Falls

Art Room at Old Stone Farmhouse

4.88 out of 5 average rating, 410 reviews

A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.

Cabin in Rhinebeck

Sunset Bungalow-Mt views on 130acre forest & falls

4.91 out of 5 average rating, 785 reviews

A spacious bedroom is shown with a queen bed adorned in floral bedding. A cozy fireplace is built from natural stone, surrounded by decorative elements. A small breakfast table with black chairs is positioned near windows draped in bright yellow curtains, allowing natural light to fill the room.

Farm stay in New Paltz

The 1772 Lefevre Stonehouse Suite

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 107 reviews

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4.98 out of 5 average rating, 142 reviews

A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.

Flat in Chester

Private Country Getaway

5 out of 5 average rating, 232 reviews

Flat in Wappingers Falls

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

Apartment in Vernon Township

A spacious living area features a cozy sofa adorned with a throw blanket, set against a stone fireplace. A flat-screen TV is mounted above the fireplace. Nearby, a small dining table with two chairs sits near large windows that offer views of the outdoors.

4.94 out of 5 average rating, 893 reviews

Appalachian Lodge Top Floor w/views

4.93 out of 5 average rating, 370 reviews

A spacious main area is highlighted by a large bed covered with a floral quilt. A comfortable sofa is positioned nearby, while a wooden café counter with four chairs overlooks natural light coming through the three windows. A coffee bar and kitchen appliances are integrated into the space.

Flat in New Paltz

Peaceful and Private Boutique Apartment *Pool*

Guest house in Stanfordville

A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.

4.93 out of 5 average rating, 188 reviews

Eco Cottage in the Woods

Guest house in Pound Ridge

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.

4.94 out of 5 average rating, 108 reviews

A Lovely Cottage in the Woods