Family-friendly holiday rentals in Orange County

4.99 out of 5 average rating, 129 reviews

A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.

Cottage in Warwick

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

A spacious backyard features a heated pool surrounded by a stone patio, overlooking the scenic lake. Vibrant fall foliage adorns the landscape, and the serene water reflects the clear sky. A cozy home is visible, nestled against the lush greenery.

4.97 out of 5 average rating, 105 reviews

Luxury Villa w Lake View & Private Heated Pool

Greenwood Lake Outlook, top-rated luxury getaway - 1 hour from NYC. Newly renovated home, surrounded in serene nature with stunning lake views & many amenities. Kids & pets friendly. Close to ski resorts. Fun all seasons. A few guest review highlights: ✭✭✭✭✭ This was the best Airbnb we’d ever stayed in. ✭✭✭✭✭ Words can’t describe how beautiful the house and the views are. ✭✭✭✭✭ If I could give this place 10 stars, I would!!! ✭✭✭✭✭ This is a true vacation resort to enjoy to the fullest.

5.0 out of 5 average rating, 220 reviews

Panoramic Lakeviews & Lush Garden | Beach Access

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features hundreds of plants and a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. Guests get access to a private community beach. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, fireplace, smart TV, record player and board games.

4.99 out of 5 average rating, 201 reviews

A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.

Cottage in Monroe

Cozy Lake Cottage

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets in any temps from inside or out, or coffee in the tree hut! Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

4.96 out of 5 average rating, 488 reviews

A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.

Cabin in Greenwood Lake

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Cottage in Greenwood Lake

An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.

4.97 out of 5 average rating, 387 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245

4.94 out of 5 average rating, 391 reviews

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

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 1–6 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.

A six-person Jacuzzi hot tub is positioned on a patio, overlooking a serene lake surrounded by trees. The bubbling water reflects the greenery, creating a peaceful atmosphere for relaxation.

4.96 out of 5 average rating, 321 reviews

Stylish Lakeside Cottage with Hot Tub

Welcome to Greenwood Lakeside Cottage, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

4.92 out of 5 average rating, 378 reviews

A modern kitchen area is presented with open wooden shelves displaying dishes, glassware, and decorative items. Below, a gas stove and black refrigerator are complemented by a light fixture and a collection of utensils, offering a functional and organized space.

Cottage in Goshen

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.

4.97 out of 5 average rating, 173 reviews

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.

Flat in Chester

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.

4.95 out of 5 average rating, 443 reviews

Cabin in Wurtsboro

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.

The lakeside property features a well-manicured lawn leading to the water's edge, complemented by a dock and a single kayak. Lounge chairs are arranged near a shaded gazebo, with a stone pathway guiding guests towards the house, which is framed by lush greenery.