
Family-friendly holiday rentals in Ulster County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Ulster County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Top 5% - Private & Modern Farmhouse, BBQ, 2hrs NYC
Super private, pet-friendly 13 acre solar powered*, modern farmhouse 2 hours from NYC in Catskills. ✔ Large backyard w/ firepit ✔ Dogs allowed** ✔ 229Mbps wifi ✔ Screen-in porch w/ outdoor dining ✔ 65” Smart TV with Apple TV in living room ✔ 50” Smart TV with Apple TV in guest bed ✔ Bluetooth sound system ✔ Memory foam mattresses ✔ Back deck w/ BBQ grill ✔ Indoor fireplace ✔ Onsite parking 10 mins → Vernooy Falls 20 mins → Minnewaska State Park, Mohonk Preserve & Ashokan Rail Trail

Stylish and Cozy Mountain Retreat
Private entrance into a stylish, cozy upstairs studio in artist's mid-century home near The Ashokan Reservoir. The Catskills are the destination for hiking, art, skiing, swimming or checking out the local food scene and breweries - all within minutes. Guests have the second floor to the home with no shared spaces with host. Outdoor seating with grill, barn with bocci and other yard games. King size bed, day bed with plush bedding. Spacious new bathroom with tiled shower and skylight.

Catskill Cabin | Fire Pit | Screened Porch | Pets
Take a leisurely walk under the towering trees in the quiet wooded acre surrounding our cozy, alpine-inspired cabin with contemporary bohemian touches. Sleep in upstairs under deep-set skylights, observe wildlife out our large picture windows, or curl up by the fire on the rustic screened porch. Daydream on our hammock or dine alfresco taking advantage of our barbeque. On a clear night, it is easy to stargaze up through the tall trees, perhaps while toasting marshmallows fireside.

The Metsämökki - A Finnish Cabin in the Woods
The Metsämökki is a small Finnish cabin in the foothills of the Catskill Mountains. Originally a sauna that was shipped here from Finland. We renovated it to a tiny house that offers complete privacy. Enjoy the babbling brook while sitting on the deck and taking in the surrounding nature. We're not offering high-tech or glamour but this cabin is a beautiful retreat from the busy city. **Check out our new midweek discounted rates and enjoy a little extra time for a great price!!

Dreamy Catskills mountain getaway w/ yoga studio
This stunning house has been renovated and offers total privacy and serenity - sitting on 5 acres at the end of a quiet road. The Mountain Terrace has an indoor wood stove, a deck with a beautiful view, a fire-pit, 3 bedrooms and 2 bathrooms and a double high ceiling in the main living space. There is a washer/dryer, a dishwasher an artist cabin and a private yoga studio. An easy 15 min drive to Livingston Manor for great restaurants, shopping and activities. Pet friendly.

The Treecastle at the Roundhouse Homestead
The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Modern creekside cabin in the Catskills
Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Willow Treehouse - secluded, unique, romantic
The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Catskills Farmstay: Pool, Sauna, Animals, Mt Views
Make the most of winter’s final weeks and take a break upstate. Escape the city bustle for a cozy, restorative stay at Napping Horse Farm! The Bird's Nest is a light-filled retreat nestled on 30 secluded acres at the foot of Overlook Mountain. Perfect for couples, solo travelers, and small families seeking wellness, stillness, and a memorable experience with rescue farm animals. Nature, comfort, and deep calm just 2 hours from NYC.

ENTER HOME - Minimalistic style warm & inviting
ENTER our HOME with an inviting comfortable setting filled with natural light and clean lines inspired by Nordic Design. Full new kitchen with all Bosch appliances including washer and dryer. Our home is designed to embrace the beautiful nature around you and to bring peace and comfort to your stay. ENTER HOME is great for individuals, couples, or families with kids. AC in both bedrooms only

Black A-Frame: Catskills Cabin
Escape to Black Pines A-Frame, a fully renovated 1961 cabin nestled in the Catskill Mountains in Kerhonkson, NY. Named one of the “Coolest A-Frames in NY” by the New York Post, this charming retreat blends rustic character with modern comforts. Set on two private acres, it offers stunning wooded views and a warm, inviting atmosphere.
Popular amenities for Ulster County family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain View Hideaway

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

midcentury mod * POOL * walk out trail 2 mohonk

Country Tiny Home w/ King Bed & Hot Tub 18 Acres

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Hot tub with stunning views, 5 min to Woodstock

Stream Come True | Hot Tub, Ski, Hike, Relax
Family- and pet-friendly home rentals

Dave's Milk Barn

New Paltz Guest Cabin Nestled In The Woods

Modern Catskills Cabin

Unique BellEayre River retreat

The Stone House

Catskill Mtn Streamside Getaway - With EV Charger

Woodstock Mountain Cottage w/ Pool /Swim

Bluebell - Kos Retreats @ Frogs Hollow Farm
Family-friendly home rentals with a pool

Hike & Sauna! Modern Mountain Escape

The Little Shelter at Gunks EcoLodge

Peaceful and Private Boutique Apartment *Pool*

Design Scandi Retreat, Heated Pool, Dogs Welcome

MODERN FARMHOUSE in the WOODS

Catskills Cabin Retreat w/Heated Saltwater Pool

New Paltz dog friendly retreat w/ salt water pool

Summer Paradise - Pool, Fire-pit, Nursery!
Destinations to explore
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- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Plattekill Mountain
- Windham Mountain
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Taconic State Park
- Hunter Mountain Resort
- Mount Peter Ski Area
- Kent Falls State Park
- Bear Mountain State Park
- Wawayanda State Park
- Walkway Over the Hudson State Historic Park
- Storm King Art Center
- Millbrook Vineyards & Winery
- Poets' Walk Park
- Hudson Chatham Winery
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