Kid-friendly vacation rentals in Philipstown

4.87 out of 5 average rating, 184 reviews

A wooden deck is shown featuring a large umbrella providing shade over a seating area. A patterned rug lies on the floor, accompanied by a potted plant. Two lounge chairs and a small table create a comfortable outdoor space, surrounded by lush greenery.

Cabin in Saugerties

Private Woodstock Getaway w Hot Tub

Relax in this cozy retreat on a private road. Snuggle up by the fire, play some records, relax on the sunny deck, or jump in the hot tub. Cook dinner in the fully stocked kitchen or grill on the deck and enjoy your meal in the screened in porch. The master bedroom has a king-size bed and quality linens, as do the other two bedrooms, one with a queen and one with 2 twins beds. Relax downstairs in the family room, watch a movie, or cozy up by the wood burning stove. Short drive to the town of Woodstock ! Close to skiing, hiking & swim holes! $50 extra for dogs. No cats. Use hot tub at your own risk. The whole home is yours except the garage remains closed. Always available if any issues arise, but not on the property. The house is set back on a private road. It's a genuine retreat, but still only a short drive from the shops and restaurants of Woodstock and Saugerties. Local hikes abound, and venture a little further to find swimming holes and skiing. If you have a small child, I suggest bringing a gate as there are stairs to the basement.

Cottage in Greenwood Lake

A bright living area features a comfortable sectional sofa and a cozy armchair arranged around a central coffee table. Large windows allow natural light to fill the space, complemented by soft furnishings and a neutral color palette. A ceiling fan provides a gentle breeze.

4.84 out of 5 average rating, 206 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Just a little more than an hour away from NYC and a 4-min drive to the lake, this pet-friendly private retreat offers a hot tub, family room, spacious yard with fire pit, and a deck with a grill and comfy seating. The renovated interior has all the comforts of home including a full kitchen & streaming capabilities. Incredible perks include complimentary lake access at nearby beach, family board games, children's books, toys & a mini game table for ping-pong, air hockey, football & billiards!

4.99 out of 5 average rating, 151 reviews

The cabin features a rustic cedar shake exterior with a distinctive red front door. A spacious deck surrounds the entrance, providing a welcoming space. Vibrant autumn foliage frames the cabin, enhancing its natural setting within the forest.

Cabin in Kerhonkson

Lovely Cabin w/Piano No Car Needed Best Hiking

When you truly want to get away from it all, come experience the wilderness of the Catskills. We're nestled next to 30k acres of the Sundown Wild Forest inside the 300k acres Catskill Park, 2 hrs from NYC. Enjoy any of the 3 fireplaces located in and around the cabin after your choice of 8 hiking trails you can take from our doorstep including the cascading pools of the secluded Vernooy Kill Falls. Ecology History tour available RT private transportation from New Paltz Trailways Bus available.

5 out of 5 average rating, 121 reviews

Two wooden docks extend into the calm waters of Greenwood Lake, framed by lush trees and houses on the opposite shore. A partially cloudy sky with blue patches creates a serene atmosphere, complementing the peaceful lakefront setting.

Home in Greenwood Lake

Summer is calling! Lakefront/Hot-tub/1 hour to NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Cottage in Mongaup Valley

A hot tub is surrounded by lush greenery and illuminated by string lights, creating a serene outdoor setting. A stone path leads to the hot tub, with red chairs visible nearby, all nestled within a wooded area.

4.98 out of 5 average rating, 229 reviews

Hot Tub, Playground, 3 Acres, and Much More!

Relax with the whole family at this peaceful cottage in the trees 5 minutes from Bethel Woods - check out their upcoming events! Recently renovated cottage with hot tub, an electric fireplace, washer and dryer, dishwasher, and smart TVs. Family-friendly features include a baby gate, potty training seat, high chair, toddler-safe bunk beds, and toys Outdoor features include 2 fire pits, trampoline, jungle gym, basketball hoop, walking path, stream w/ waterfall, and 3 acres of woods to explore

4.95 out of 5 average rating, 111 reviews

An enclosed porch features two metal-framed chairs with cushions, positioned near a small table. A decorative rug with vibrant floral patterns covers the floor. A potted plant and a lantern add to the decor, with sunlight streaming through the windows overlooking the water.

Home in Lake Katrine

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

4.93 out of 5 average rating, 133 reviews

A newly renovated Victorian home showcases a striking blue exterior with white trim and a charming turret. A spacious porch, surrounded by railings, invites guests to relax outside. The property is set on a well-maintained lawn adjacent to a paved walkway.

Home in Kingston

Hightop House: Modern, Uptown, Centrally Located

Hightop House is a newly renovated Victorian home in midtown Kingston. Ideal for a WFH getaway (inhouse and coworking partnership), groups, and families. Enjoy easy access to Kingston and surrounding areas. 3 bedrooms, 2.5 baths. Large open kitchen, contemporary furnishings, brand new appliances. Walk to UPAC / Stockade District, Keegan Ales. <10 min drive to the Rondout district, Hutton Brickyards. 10min to Ashokan Rail Trail, Onteora Lake. 20min drive to Saugerties, Woodstock, Rosendale.

4.85 out of 5 average rating, 106 reviews

A well-equipped kitchen features modern appliances, including a refrigerator and oven, within bright white cabinetry. A wooden dining table with chairs sits in the foreground, while hardwood flooring enhances the spaciousness. Natural light illuminates the room from a nearby window.

Apartment in Beacon

Lovely 2 bed, 2 full bath. & private yard getaway

Bring the whole family to this super clean place with lots of room for fun. Private Yard ! kitchen/ dining room, living room, main bedroom w/king size bed & private bathroom, kid’s bedroom w/queen size bed & full bathroom across the room. This beautiful Airbnb has prime location. Across the street you will find the beautiful Madam Brett park w/waterfall and walking trail. Close to main street, train station, MT. Beacon also 8 min drive to Bannerman Castle and Dia Beacon Museum.

4.95 out of 5 average rating, 358 reviews

A serene saltwater pool is framed by lush greenery, providing a tranquil escape. Comfortable lounge chairs are positioned around the patio, inviting relaxation. The setting is peaceful, surrounded by trees that enhance the private atmosphere.

Home in Kerhonkson

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

4.9 out of 5 average rating, 131 reviews

A spacious living area features wooden walls and beams, providing a rustic ambiance. Comfortable seating arrangements include a large sectional sofa and cozy armchairs. A central coffee table sits on a decorative rug, and a wood-burning stove is positioned near a flat-screen TV.

Home in Middletown

Riverfront! Swim, Fish, Hot Tub & Game Barn.

Fish, Tube, Hot tub and Game room! All in one property! This exquisite riverfront home has 3 bedrooms and a sleeping loft. This magical property is 7 acres on the River. Bellayre beach 15 mins and Windham mountain biking 30 mins. Hike, s’mores by the fire, hang out in the 3 season game barn equipped with a pool table and darts, have a drink in the riverside hot tub. 5 mins to retro bowling and restaurants. NO FIRST TIME RENTERS ID VERIFIED/REVIEWED RENTERS ONLY.

4.99 out of 5 average rating, 190 reviews

The entrance features a series of stone steps leading to a double door with glass panels. The surrounding area is adorned with blooming plants and greenery, with decorative iron railings providing a welcoming atmosphere.

Apartment in Hoboken

“Fantastic” apartment in “beautiful” townhouse

This is a sunny, spacious and private, top floor-through apartment in an owner-occupied Victorian townhouse. There is a large master bedroom, a bunk room, living and dining rooms. You also will enjoy the well-equipped kitchen and renovated bathroom with skylight. This apartment is in a prime uptown Hoboken location close to transportation to Manhattan and local restaurants, coffee houses and shopping. Perfect for families, professionals, Stevens visitors and couples.