Family-friendly holiday rentals in Woodbury

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

Indoor spaces · Kitchen · Parking

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 spaces · Family · Sleep quality

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Family · Kitchen · Getting around

Serene Private Home • Light-Filled • Hot Tub •Deck

Spacious 3,600 sq ft home designed for comfort and ease in upstate New York 🌿 Light-filled rooms, open flow, and a hot tub + deck create a calm, elevated stay ✨ An open layout with multiple living areas makes it easy to gather while still having space to relax and unwind & enjoy throughout. The space functions as a self-contained part of a larger property, offering privacy and independence without feeling segmented. A comfortable base near farms, villages, dining, and outdoor activities.

Kitchen · Family · Pool

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–4 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

Family · Indoor spaces · Parking

Gorgeous Suite w/ Private Entrance & Farm Friends

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Family · Indoor spaces · Air conditioning

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

Indoor spaces · Family · Nearby

Secluded mountain top horse property near W. Point

"Green acres is the place to be, farm living is the life for me!" This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 mins from West Pt. situated on a mountain top. This private little space is a nature lovers paradise. Come, watch the horses from the front deck, enjoy fresh eggs in the morning, relax by the outdoor fire pit, star gaze & hike/explore forest trails right out the front door.

Family · Kitchen · Hospitality

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

Indoor spaces · Kitchen · Air conditioning

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 15 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.

Indoor spaces · Kitchen · Bathroom

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225

Family · Kitchen · Check-in

Spacious, bright 5 bedroom house near West Point

Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Indoor spaces · Kitchen · Accuracy