Family-friendly holiday rentals in Town of Mamakating

4.97 out of 5 average rating, 110 reviews

A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.

Chalet in Pine Bush

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

4.93 out of 5 average rating, 193 reviews

The interior of the bus features a cozy layout with a full bed and a twin bed, both with new linens. A rustic storage unit is present along one side, while soft overhead lighting and a small dining table enhance the warm ambiance. A compact electric fireplace adds comfort.

Bus in Pine Bush

School Bus Glamp w/HotTub~15min to Gunks/New Paltz

Experience a unique stay in a magic school bus on 10 acres! 15min to Gunks, New Paltz, Angry Orchard HQ, Minnewaska &more! Relax in the hot tub in the morning or sit under the stars at night. Two beds; twin & full w/bedding. Heater/AC, mini-fridge, Keurig w/coffee & mugs. Swing set & trampoline for kids. Private outdoor set up w/(year-round) hot tub, dining area, fresh water sink & fire pit await you. Wonderful bakery & outdoor store just down the road. Enjoy Gunks glamping with a relaxing spa!

4.95 out of 5 average rating, 378 reviews

A hot tub is positioned under softly glowing string lights along a snowy bank, inviting relaxation. Surrounding the tub are wooden chairs and a table, with the cascading brook flowing nearby. Snow-covered trees frame the serene winter scene.

Cabin in Wurtsboro

The Water House - Winter Spa on a Cascading Brook

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

4.96 out of 5 average rating, 266 reviews

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.

Cottage in Bethel

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

4.96 out of 5 average rating, 516 reviews

A view from the cabin reveals a queen mattress framed by sheer curtains. Outside, red chairs encircle a stone firepit, with expansive mountain views visible in the distance. Natural light floods the space, enhancing the connection to the outdoor environment.

Campsite in Accord

Canyon Edge off - grid Bungalow

The ideal perch to reflect, connect, and participate in nature's beauty. This unique structure blends pure nature with simple comfort. Sitting canyon side, you sleep beneath the canopy and wake to the mountains of the Hudson Valley. Welcome the spring buds of our forest oaks; Make summertime memories into the night by the fireside; Enjoy natures fall masterpiece of changing of the leave; Reflect on the year as the snowflakes fall Read listing fully, we’re available for any Q’s!

4.81 out of 5 average rating, 947 reviews

A cozy living room features a stone fireplace surrounded by plush seating. Wooden beams accent the ceiling, enhancing the rustic charm. Soft light glows from nearby rooms, creating a warm and inviting ambiance. Decor elements reflect nature-inspired design, adding character to the space.

Cottage in Kerhonkson

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Escape to a serene cottage nestled on the Shawangunk Ridge. Unwind by the fireplace, soak in the private infrared sauna (with direct patio access), or relax outside on the natural stone terrace with a firepit and forest views. Crafted with care—from a 100-year-old reclaimed wood dining table to a curated “meaningful library” and hidden messages—this space invites calm, curiosity, and connection. Near trails, lakes, and local adventure. Thoughtful, cozy, and quietly unforgettable.

4.92 out of 5 average rating, 353 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.

4.96 out of 5 average rating, 179 reviews

A welcoming studio space is furnished with a pink sofa, a wooden coffee table, and a dining area with a table and chairs. Light enters through a sliding glass door, revealing views of the wooded backyard. A small television is positioned near the seating area.

Flat in Tillson

Woodland Neighborhood Retreat

Relax in a cozy studio in the peaceful woods. Tasteful high-quality touches will have you feeling comfortable right away! This is an ideal space for up to 2 adults and up to 2 children. We live upstairs & offer self-check-in. A rare find in the Hudson Valley, our neighborhood is mostly flat, with walkable, quiet roads, and excellent bird-watching. It's an easy bike ride to connect to the vast state-wide rail trail system & all that the Mohonk Preserve has to offer.

4.94 out of 5 average rating, 108 reviews

The rustic log cabin is framed by vibrant greenery, with colorful flowers blooming in the foreground. A cozy red exterior is complemented by a steep brown roof. Outdoor seating is visible nearby, set amongst the natural landscape of trees and shrubs.

Cabin in Wurtsboro

Catskills log cabin w/waterfall, views & hot tub

Experience total privacy and relaxation in our magical log cabin on 10 acres of woods, 90-minutes from NYC! Our home sits atop a bedrock cliff, with gorgeous, untouched Shawangunk mountain views and the peaceful sounds of the river and 30-ft. waterfall running below. The cabin is wonderfully cozy yet spacious, rustic while having most modern amenities provided to you. Enjoy total seclusion close to so many things to see and do....best of both worlds!

4.82 out of 5 average rating, 153 reviews

The tiny house exterior is illuminated by string lights, creating a warm atmosphere at night. A set of wooden stairs leads to the front door, framed by two inviting chairs on the porch. Surrounding trees provide a natural backdrop, enhancing the secluded feel.

Tiny home in Rock Hill

Trails Head Tiny House

Private and off-grid tiny home near the Neversink Unique Area hiking trails. This tiny house is approximately a tenth of a mile from guest parking. A marked trail to the site with trail markers for easy direction. This tiny house has solar powered WIFI and lights. This is not an insulated structure and during the winter months there is no running water. The outhouse is located about 50 feet from the tiny house.

4.78 out of 5 average rating, 649 reviews

The exterior of a historic stone farmhouse is shown, featuring a vine-covered wall and landscaped garden. Steps lead to the entrance, surrounded by greenery and floral elements, with large windows allowing natural light. The serene outdoor setting reflects the charm of the surrounding countryside.

Flat in High Falls

Art Room at Old Stone Farmhouse

Downstairs Victorian style private suite with it's own entrance to large front hall, bedroom & bathroom in an old stone farmhouse filled with mid-20th-century artwork. Easy access to outdoors. The house is one of the original deeds in Clove Valley dating back to the 1700s. The home has lots of character on a sustainable farm adjacent to the Mohonk Preserve & 7 miles to Minnewaska State Park.

4.99 out of 5 average rating, 172 reviews

A modern cabin in a snowy landscape is framed by tall trees blanketed in white. The building features large glass doors on the front, and a cheerful snowman stands to the side, adding a playful touch to the winter scene.

Cabin in Ellenville

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 brand new (completed Dec 2023) and located about 2 hours from NYC, close to many local attractions 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

Popular amenities for Town of Mamakating family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 166 reviews

An outdoor hot tub is situated in a cozy yard surrounded by autumn leaves. Warm light spills from the windows of the cabin, casting a welcoming glow. Hanging string lights illuminate the path leading to the house, enhancing the tranquil evening atmosphere.

Cabin in Cuddebackville

Creekfront Cabin Sauna & Hot Tub Hikers Hollow

4.89 out of 5 average rating, 99 reviews

A cozy living area features wooden walls and a plush sectional sofa, complemented by a dark coffee table. A smart TV is visible on the wall, while a doorway leads to a bathroom. Natural light enhances the inviting atmosphere.

Home in Glen Spey

Cozy and Quiet Lakeview House

4.91 out of 5 average rating, 244 reviews

The A-frame cabin is set against a backdrop of lush greenery, featuring a spacious deck and an outdoor seating area. A circular arrangement of black chairs with a fire pit in the center is surrounded by gravel, inviting relaxation and gathering.

Cabin in Ellenville

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

5 out of 5 average rating, 205 reviews

The inviting exterior of a cozy cabin is surrounded by lush greenery, with warm lights illuminating the covered porch. A fire pit is featured at the forefront, surrounded by four Adirondack chairs, creating a welcoming space for evening gatherings.

Cottage in Kerhonkson

Ye Little Wood | Cozy Forest Cottage with Hot Tub

4.9 out of 5 average rating, 168 reviews

A red cabin with stone accents is surrounded by greenery, featuring a wooden porch with large windows. A gravel path leads to a patio area with a red umbrella, seating, and a grill in the fenced backyard, providing a welcoming outdoor space.

Cabin in Milford

Riverfront Cabin on the Delaware

4.88 out of 5 average rating, 298 reviews

A tiny cabin with a unique Japanese-inspired design is nestled among tall trees, accompanied by a gravel pathway and a small fire pit. The cabin's natural wood exterior blends with the forest surroundings, creating a serene atmosphere beside a flowing brook.

Cabin in Downsville

Tiny glamping cabin with mineral spring hot tub

Guest house in Forestburgh

A hot tub is visible in the foreground, with feet partially submerged in water. In the background, a vibrant sunset displays hues of purple and orange over a serene outdoor landscape, framed by trees and an outbuilding.

4.97 out of 5 average rating, 448 reviews

Guesthouse On old 1879 Farm. Hot tub, hiking.

4.94 out of 5 average rating, 187 reviews

A modern, single-story home is situated among tall trees, featuring a welcoming front porch with two blue chairs. A charcoal grill is positioned nearby on a gravel path, and ample greenery surrounds the property, creating a serene outdoor environment.

Home in Kerhonkson

Shawangunk House

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 152 reviews

A wide view of a grassy field is presented, bordered by trees and rolling hills in the distance. The sky appears clear and blue, creating a serene backdrop for outdoor activities. A small firepit made of stone is positioned on the lower left.

Campsite in Kerhonkson

tent camping $25/person/night -stunning mt views.

4.95 out of 5 average rating, 165 reviews

The cottage is set on a spacious lawn, surrounded by trees, showcasing a well-maintained exterior with a gray facade and a gravel walkway leading to the entrance. A chimney indicates the presence of a cozy fireplace inside.

Cottage in Ellenville

Shingle Gully Cottage

5 out of 5 average rating, 163 reviews

A cozy living area is highlighted by a corner fireplace and a flat-screen television. A sectional sofa with cushions and an armchair create a comfortable seating arrangement. A decorative shelving unit displays greenery and decorative items, while warm lighting adds a welcoming touch.

Bungalow in Hurleyville

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

4.91 out of 5 average rating, 108 reviews

A spacious loft area features a queen-size bed with decorative pillows and a comfortable futon sofa positioned against a wooden wall. Natural light enters through large windows, illuminating a colorful area rug that spans the floor. A fan is mounted on the ceiling.

Guest house in Wurtsboro

Hiker’s Haven, a Cozy Cabin above Bashakill Refuge

4.87 out of 5 average rating, 412 reviews

A gentle waterfall cascades over rocky terrain, surrounded by autumn foliage in varying shades. The water flows into a clear pool, with smooth stones lining the edges. Tall trees in the background create a lush, green canopy, while fallen leaves blanket the ground.

Cabin in Rhinebeck

Sunset Bungalow-Mt views on 130acre forest & falls

4.96 out of 5 average rating, 449 reviews

Feet are seen dangling over a gently flowing stream, with a snowy landscape surrounding the banks. The cabin is glimpsed in the background, its vibrant green color contrasting against the natural elements and the soft glow of early sunlight filtering through the trees.

Cabin in Vernon Valley

Serenity Cabin, the historic waterfall cabin!

5 out of 5 average rating, 101 reviews

The exterior of a blue farmhouse cottage is shown, featuring a metal roof and a welcoming front porch with two white chairs. Lush green grass surrounds the house, complemented by blooming hydrangeas and decorative potted plants. Trees and open land are visible in the background.

Cottage in Grahamsville

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

4.93 out of 5 average rating, 230 reviews

The interior of the tiny house features warm wooden walls and ceilings, complemented by a cozy kitchen area. A dining table with two chairs sits beside a large window, allowing natural light to fill the space. A staircase leads to a lofted sleeping area.

Tiny home in Woodridge

Outlier Inn Tiny House 1 on Farm Upstate Catskills

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 396 reviews

A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.

Cottage in Kingston

Kapitan’s Cottage Private Upstate Catskill Retreat

4.98 out of 5 average rating, 142 reviews

A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.

Flat in Chester

Private Country Getaway

4.95 out of 5 average rating, 414 reviews

The living area features a comfortable couch and armchair, with large windows providing natural light and views of the outdoors. A wooden dining table with four chairs is positioned near the windows, while a coffee table sits in front of the couch. Shelves hold various books and decorative items.

Guest suite in New Paltz

Airy & Private Escape on Mountain Rest Road *Pool*

4.94 out of 5 average rating, 221 reviews

Home in Narrowsburg

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

Apartment in Vernon Township

The living area is highlighted by a large picture window, offering panoramic views of the slopes. A cozy couch is positioned near a modern fireplace, while a wooden dining table and chairs complete the open concept space. A wall-mounted television enhances the inviting atmosphere.

4.92 out of 5 average rating, 378 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

4.82 out of 5 average rating, 200 reviews

The collage showcases different areas of the home and yard. An outdoor seating area with a pergola and hot tub invites relaxation, while a spacious pool lies in the background. The living area features a cozy setup with a Peloton bicycle, and the kitchen area includes a bar, enhancing social gatherings.

Cottage in Kerhonkson

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

4.86 out of 5 average rating, 105 reviews

A serene landscape capturing a peaceful lake surrounded by dense greenery. The calm water reflects the trees and sky, creating a tranquil scene. Soft ripples disturb the surface, while patches of grass and fallen branches line the water's edge.

Home in Woodridge

Family Fun Getaway w/Pool/Hot tub Canoe