Family-friendly vacation rentals in Woodridge

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 · Accuracy

Pocono Castle: Dungeon Escape Room & Private Pond

Sleep in a Fairy Tale at Pocono Castle! Live the dream in this 2,300 sq. ft storybook retreat, where you’ll sleep like royalty in a real fairy tale castle. Unwind in luxury with a bubbling hot tub, a cedar sauna, and endless magical touches. Dress up as Kings, Queens, or Knights and explore the grounds, featuring a private one-acre pond & maybe you’ll catch a Golden Fish! With enchanting bedrooms, outdoor adventures, and unforgettable charm, this is the OMG getaway you’ve been waiting for!

Indoor spaces · Family · Amenities

Stunning Passive Solar Cabin on 135 acres & pond

Just the perfect cabin. This newly built, passive solar house has a wood-burning stove, incredible views and is drenched with light. The house is intimate yet connected to the outside, with total seclusion and every imaginable modern convenience! It’s an architect-designed marvel of concrete, glass and reclaimed wood that sits on 135 acres of field and forest with a lovely swimming pond and miles of hiking trails. The cabin sleeps up to 6 people in two bedrooms and a spacious sleeping loft.

Kitchen · Family · Grill

Serene Home in the Catskills Woods

Welcome to your countryside escape! Perched in the heart of scenic Sullivan County, Davos on the Hill is your serene home away from home—the ultimate retreat for hiking, rest, and recharging. We’ve curated a space that balances minimalist design with total comfort. Whether you’re whipping up a gourmet meal, ordering a local pizza for movie night, or gathering for board games by the fireplace, you’ll find everything you need right here. Slow down, breathe deep, and make some memories.

Family · Indoor spaces · Layout

Dutchhillcottage, gem in the southern Catskills.

Just 85 miles from NYC! Rustic chic design cottage waiting for you and your friends or family to enjoy. Private, comfy & cozy country getaway with amazing views situated on 10 acres of rolling hills in the southern Catskills, perched on a peak at the forests edge with expansive views all the way down to the Never Sink river with beautiful suntset views from our huge deck. Plenty of ameneties. Petdog friendly. Just 2 miles down the road from newly updated Holiday Mountain Ski Resort!

Family · Kitchen · Parking

Dreamy A-Frame Cabin Hot-Tub | Games Room | Firept

Welcome to our 3 bedroom, 1.5 bathroom A-frame mountain escape with room to spread out and unwind. • Hot tub, fire pit, overhanging deck, and outdoor dining patio • Cinema-style movie room, pool table, darts, board games, and record player • Fully kitted gym with water rower, free weights, kettlebells, and more • Catskills foothills base, with short access to lakes, waterfalls and breathtaking hikes Book your stay and enjoy the cabin’s mix of play, rest, and forest views.

Kitchen · Family · Access

“Green Meadow Cottage”, updated 1850’s farmhouse.

Relax with friends or family in this cozy updated 19th century farmhouse cottage set on 5 acres surrounded by pasture and forest. This is truly a rural setting to enjoy the serenity of nature. Centrally located, a leisurely country drive will take you to quaint towns, spectacular hiking, fine dining and more. Visit our many breweries and distilleries or just take a drive and explore. Bring your bikes and ride the gently rolling wooded roads… or not. It’s your vacation.

Indoor spaces · Kitchen · Bathroom

Forest Spa Retreat on Cascading Brook • 90 Min NYC

Tucked into an evergreen forest, The Water House is a private spa retreat set above a cascading brook—where flowing water shapes your stay. Spend slow mornings on the deck, unwind in the hot tub, and gather by the fire pit under the stars. Find a quiet moment beside the Japanese-inspired pond. Inside, soft textures and vintage style create a warm, calming atmosphere designed to reconnect you with nature while offering the restful comfort of a boutique retreat.

Indoor spaces · Kitchen · Skiing

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Welcome to Minnewaska Cabin. A Catskills mountain cabin on a private forested lot, with a hot tub, a wood stove and king bed. The house is very new (completed Dec 2023) and located about 2 hours from NYC, close to many local attractions, like hiking trails, skiing and water sports. 20 mins from Minnewaska State park 35 mins from Legoland Goshen 20 mins from Resorts World Catskills casino 5 Mins from North East Off Road Adventures

Family · Indoor spaces · Check-in

Charming Farmhouse Getaway

Welcome to our beautifully renovated 4-bedroom, 2-bathroom and 1 mezzanine floor office space, originally farmstead, nestled on an expansive 18-acre property, with a tranquil brook flowing through its grounds. This enchanting retreat offers the perfect blend of rustic charm and modern comforts, providing an idyllic escape from the hustle and bustle of everyday life.

Indoor spaces · Kitchen · Sleep quality

Lidar West

Lidar West is a unique mountain home located in the woods by one of New York City's major reservoirs. The main house is a 1400 sqft 2 bed, 2 bath, ideal for families with kids, and there's a sleeping cabin with an additional queen bed, electric heater, and wood burning stove called Hemmelig Rom, which I built myself using oak milled on the property.

Indoor spaces · Kitchen · Comfort

Escape to a 3-Bedroom Cabin in Lower Catskills

Welcome to the Bear Lodge! Located in the Lower Catskills, the cabin is a short 90 minutes from NYC, and is centrally located to all kinds of outdoor activities. There are easy walking trails through the woods within walking distance, as well as Rails-to-Trails paths, the Neversink River, and dozens of lakes nearby.

Kitchen · Family · Value