Family-friendly vacation rentals in Woodbury

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Top-rated family-friendly rentals in Woodbury

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
4.93 out of 5 average rating, 128 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
An open living area features a modern kitchen with dark cabinetry, a central island, and stainless steel appliances. A cozy seating arrangement includes a leather sofa, a wooden coffee table, and a stylish rug. Large windows allow natural light to fill the space, connecting to the outdoors.
Home in Warwick
5 out of 5 average rating, 104 reviews

Fall Warwick Escape! Farms, Apple Pick, Ren Faire!

Fall is the BEST time to visit Warwick! You'll love this cozy & relaxing newly constructed home in the heart of Warwick's beautiful & historic Bellvale Hamlet. Enjoy the warm decor, great style, all new furniture, plenty of games & game table for pool or ping pong! Less than 10 minutes to Greenwood Lake, hiking, wineries, breweries, restaurants, Warwick Main Street, Bellvale Creamery & more! Nearby Pennings Orchard & Cidery, Legoland, Mountain Creek Resort & Spa. ~1 hr from NYC Permit # 33758

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 Mountainville
4.84 out of 5 average rating, 589 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.

Guest favorite
The cottage is surrounded by lush green grass and mature trees, offering a serene outdoor setting. A well-maintained pathway leads to the inviting entrance, while the structure features light-colored siding and large windows, creating a seamless connection with nature.
Cottage in Goshen
4.92 out of 5 average rating, 287 reviews

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Superhost
A bright bedroom features two spacious beds covered with white linens and soft blankets. Large windows and skylights fill the room with natural light, showcasing views of greenery outside. Blue curtains frame the windows, and a wicker basket with towels is positioned on a side table.
Home in Monroe
4.85 out of 5 average rating, 181 reviews

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.

Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

Guest favorite
A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.
Guest suite in Chester
4.96 out of 5 average rating, 345 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Guest favorite
A modern red barn structure is presented with a spacious balcony and a staircase leading to the second story. The building is surrounded by a grassy area, and the sky is bright with clouds. Large windows allow natural light to enter the space.
Barn in Mountainville
4.96 out of 5 average rating, 129 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.

Top guest favorite
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.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 187 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.

Guest favorite
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.
Apartment in Chester
4.99 out of 5 average rating, 136 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Top guest favorite
The exterior of a two-story home is presented, featuring a welcoming front porch with two chairs. A distinctive copper-colored roof complements the white siding and black shutters, while tall windows create a bright atmosphere. A stone pathway leads to the front entrance amidst landscaped grass.
Apartment in Chester
4.96 out of 5 average rating, 403 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Guest favorite
A cozy studio space includes a queen bed with a light-colored coverlet. A kitchenette features essential appliances, complemented by a dining area with wooden table and black chairs. A flat-screen TV is mounted on the wall, and natural light brightens the room.
Guest suite in Mountainville
4.94 out of 5 average rating, 127 reviews

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited.

Top guest favorite
A comfortable suite is featured, showcasing a spacious bed with crisp bedding and two decorative pillows. A compact sofa is positioned adjacent to a lift-top coffee table, with a kitchenette visible in the background, including a microwave and mini-fridge.
Guest suite in Haverstraw
4.94 out of 5 average rating, 384 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Popular amenities for Woodbury family-friendly rentals

Quick stats about vacation rentals that are family-friendly in Woodbury

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    820 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace