Family-friendly vacation rentals in New Windsor

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in New Windsor

  • Total vacation rentals

    Explore 10 vacation rentals in New Windsor

  • Nightly prices starting at

    New Windsor vacation rentals start at G$16,739 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,620 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 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 family-friendly rentals in New Windsor

Guests agree: these family-friendly homes 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, 159 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.

FamilyKitchenAir conditioning

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, 107 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

Indoor spacesKitchenQuiet

Top guest favorite
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
4.99 out of 5 average rating, 373 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.

Indoor spacesFamilyDecor

Top guest favorite
Home in New Windsor
5.0 out of 5 average rating, 103 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!

KitchenFamilyBackyard

Guest favorite
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Apartment in Newburgh
4.85 out of 5 average rating, 368 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!

FamilyIndoor spacesSolo travel

Top guest favorite
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
4.97 out of 5 average rating, 452 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.

FamilyKitchenAccess

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, 129 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.

FamilyIndoor spacesParks

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, 520 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.

Indoor spacesFamilyCheckout

Top guest favorite
A charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.
Cabin in Fishkill Village
4.97 out of 5 average rating, 147 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain, next to massive forest preserve. 90 min from NYC but feels like you're way upstate. 130+ 5-star reviews! Cozy deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + twin-size mattress day bed on the porch. Fast WiFi. Fire pit and stacks of cut wood. Plus waterfall area with meditation pier (but waterfall only active Apr-Jun) 5 miles from Beacon restaurants & Cold Spring hiking trails.

Indoor spacesFamilyCheckout

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, 158 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.

KitchenFamilyAmenities

Guest favorite
Barn in Mountainville
4.95 out of 5 average rating, 164 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. Strong WIFI.

Indoor spacesKitchenAmenities

Guest favorite
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, 225 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.

KitchenFamilyCondition

Popular amenities for New Windsor family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
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.
Apartment in Philipstown
4.9 out of 5 average rating, 276 reviews

Foxglove Farm

KitchenIndoor spacesPool

Top guest favorite
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.
Guesthouse in Beacon
4.95 out of 5 average rating, 418 reviews

Cozy Mountainside Suite - Minutes from Beacon

KitchenFamilyRiver

Top guest favorite
A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.
Home in Accord
4.99 out of 5 average rating, 104 reviews

Accord River House

FamilyKitchenView

Top guest favorite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties
4.99 out of 5 average rating, 153 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Indoor spacesFamilyWifi

Superhost
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
4.87 out of 5 average rating, 149 reviews

Modern Upstate Gem Surrounded by Trees and Hot Tub

HospitalityLocationCleanlinessDecorKitchenIndoor spacesComfortHot tubAccuracyBathroomNearbyFamilyGetting aroundSleep qualityQuietTVBackyardAmenitiesConditionOutdoor spacesHikingPetsGrillCheck-inViewLayoutParksCheckoutValueHeatingWalkabilityWifiLaundrySolo travelAccessAir conditioning

Top guest favorite
The open living space features a large wooden table at its center, surrounded by chairs. Floor-to-ceiling windows flood the area with natural light, offering views of the outdoors. Recessed lighting and plants accentuate the high ceilings and triangular architecture.
Home in Beacon
4.97 out of 5 average rating, 466 reviews

River & Mtn Views - Jacuzzi - near Metro North

ViewHospitalityHot tubLocationWalkabilityDecorIndoor spacesCleanlinessGetting aroundKitchenComfortNearbyAmenitiesFamilyBathroomCheck-inAccuracyRiverSleep qualityCheckoutGrillOutdoor spacesHikingQuietParksBikingLayoutConditionValueAir conditioningWifiParkingNoiseAccessTVBackyardHeatingLong stayBreakfastSolo travel

Guest favorite
An open-concept living room features exposed brick walls and wooden beams. A sectional sofa and two modern chairs provide seating around a central coffee table. Bright light filters through sheer curtains on the windows, enhancing the cozy atmosphere.
Home in Beacon
4.84 out of 5 average rating, 294 reviews

Cozy chic Beacon retreat near Main St w hot tub

LocationWalkabilityComfortCleanlinessHospitalitySleep qualityIndoor spacesDecorKitchenNearbyFamilyBathroomHot tubAmenitiesConditionAccuracyCheck-inHikingQuietGetting aroundBackyardGrillTVPetsParkingValueOutdoor spacesCheckoutAir conditioningLaundryNoiseAccessLayoutWifiParksHeatingShared spaces

Superhost
A private hot tub sits on a cement pad, surrounded by greenery and trees. In the background, lounge chairs are arranged in a clearing, adding to the serene outdoor setting.
Home in Newburgh
4.92 out of 5 average rating, 106 reviews

Charming Getaway 16mi to West Point!

HospitalityComfortCleanlinessLocationHot tubAccuracyNearbyNoiseCheck-inFamilyIndoor spacesPetsQuietSleep qualityKitchenBathroomCheckoutDecorHikingBackyardValueAmenitiesOutdoor spacesHeatingGetting aroundConditionAir conditioningLaundryWalkability

Family-friendly home rentals with a pool

Guest favorite
Farm stay in Saugerties
4.97 out of 5 average rating, 241 reviews

Catskills Farmstay: Pool, Sauna, Animals, Mt Views

HospitalityLocationFamilyComfortOutdoor spacesCleanlinessViewIndoor spacesPoolNearbySleep qualityPetsDecorAmenitiesHikingAccuracyKitchenGetting aroundRiverQuietTVBathroomGrillLaundryWifiWalkabilitySolo travelConditionValueAir conditioningLayoutCheckoutCheck-inLong stayBikingSkiingHeatingHot tubNoise

Top guest favorite
A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.
Home in Cold Spring
4.95 out of 5 average rating, 177 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

HospitalityLocationFamilyIndoor spacesPoolComfortOutdoor spacesKitchenBathroomAmenitiesCleanlinessDecorNearbySleep qualityViewAccuracyHeatingGetting aroundGrillHikingLayoutBackyardConditionQuietCheck-inTVCheckoutLaundryAccessLong stayAir conditioningRiverValueWifiWalkabilityHot tubNoiseShared spaces

Top guest favorite
Home in New Paltz
4.98 out of 5 average rating, 545 reviews

midcentury mod hot tub*walk out trail R2R/Mohonk

HospitalityLocationCleanlinessKitchenPoolComfortIndoor spacesOutdoor spacesPetsFamilyDecorViewAmenitiesNearbyHikingBackyardSleep qualityAccuracyBathroomWalkabilityQuietGetting aroundLayoutBikingConditionAccessCheck-inTVGrillCheckoutBreakfastHot tubValueAir conditioningParksLaundryLong stayWifiHeatingRiverBeachParkingSolo travelNoise

Guest favorite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester
4.97 out of 5 average rating, 175 reviews

Private Country Getaway

HospitalityFamilyLocationCleanlinessComfortPoolIndoor spacesOutdoor spacesViewSleep qualityNearbyAccuracyCheck-inDecorBathroomKitchenBackyardGrillValueAmenitiesGetting aroundConditionLayoutAir conditioningQuietWifiHikingWalkabilityAccessSkiingTVHeatingParkingBreakfastHot tubNoiseCheckout

Top guest favorite
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, 693 reviews

Country Getaway - Close to Hiking & Storm King

HospitalityCleanlinessLocationComfortIndoor spacesAccuracyNearbyQuietSleep qualityHikingValueBathroomCheck-inKitchenGetting aroundAmenitiesHeatingOutdoor spacesDecorAccessTVGrillConditionViewCheckoutAir conditioningFamilyPoolWifiNoiseSolo travelParkingParksLong stayLayoutWalkabilityLaundryBackyardBikingSkiingShared spaces

Top guest favorite
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
4.95 out of 5 average rating, 132 reviews

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

HospitalityCleanlinessComfortIndoor spacesFamilyPoolLocationOutdoor spacesAccuracyDecorKitchenQuietNearbyGetting aroundSleep qualityBackyardConditionAmenitiesTVCheck-inBathroomGrillPetsCheckoutLayoutAir conditioningHikingParkingViewAccessValueHeating

Guest favorite
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz
4.88 out of 5 average rating, 233 reviews

Scenic River View Escape | New Paltz

HospitalityLocationCleanlinessComfortIndoor spacesFamilySleep qualityHot tubViewAccuracyKitchenDecorBathroomNearbyRiverOutdoor spacesAmenitiesConditionHikingQuietCheck-inAir conditioningValueCheckoutTVParkingAccessGetting aroundBackyardGrillLayoutWalkabilityParksWifiLaundryLong stayBiking

Top guest favorite
The image shows a well-kept swimming pool surrounded by a fenced area and lush greenery. Brightly colored flowers in a hanging planter add a touch of color to the foreground. Poolside lounge chairs are arranged on a textured surface, inviting relaxation.
Apartment in Wappingers Falls
5.0 out of 5 average rating, 249 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

HospitalityCleanlinessComfortLocationAmenitiesPoolKitchenSleep qualityNearbyBathroomDecorAccuracyQuietIndoor spacesBreakfastHikingOutdoor spacesGetting aroundCheck-inLaundryLong stayCheckoutValueViewAccessGrillWifiBackyardTVParksLayoutHeatingParkingFamilyWalkabilityRiverConditionAir conditioning