Family-friendly vacation rentals in Round Top

4.99 out of 5 average rating, 213 reviews

Timberwall Ranger Station | Your Upstate Base Camp

The Timberwall Ranger Station is the perfect home base for your peaceful upstate escape. Located minutes from Woodstock, Saugerties, and Kingston, this breathtaking hand-built cabin is close to all the Catskills and Hudson River Valley have to offer. The cabin is a restful place year-round: for enjoying spring birdsong at breakfast; swaying away an afternoon in a breezy summer hammock; starry skies and luscious wines around an autumn campfire; a cozy winter morning amidst freshly fallen snow.

KitchenFamilyAir conditioning

4.93 out of 5 average rating, 277 reviews

A warm living area is featured, showcasing wooden walls and a vaulted ceiling. Comfortable seating is arranged around a coffee table with an assortment of plants. Large windows reveal a snowy landscape, while shelves display books and decorative items.

Cabin in Maplecrest

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

KitchenIndoor spacesHospitality

An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.

4.97 out of 5 average rating, 167 reviews

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

FamilyIndoor spacesAir conditioning

4.96 out of 5 average rating, 117 reviews

A red cottage emerges amid a vibrant landscape of autumn foliage. The path lined with fallen leaves leads to the home, surrounded by tall trees showcasing bright yellows and oranges. Sunlight filters through the branches, illuminating the serene setting.

Cabin in Purling

Catskills Mountain Cottage - Near Hunter & Windham

The Mountain Cottage is a cozy, thoughtfully-designed home in the heart of the Great Northern Catskills, perched on a scenic hill surrounded by an acre of tall, whimsical trees. Only 2.5 hours from NYC, 20 minutes to Windham Mountain, and 25 minutes to Hunter Mountain. It is centrally located to renowned hiking trails, mountain biking, skiing, the Kaaterskill Falls, antique shopping, local apple picking, and excellent coffee, breweries, and vineyards to be enjoyed throughout the four seasons!

KitchenIndoor spacesDecor

4.96 out of 5 average rating, 218 reviews

The exterior of a chalet-style home is surrounded by lush greenery, with a stone fireplace prominently featured on the facade. The wide deck includes seating for relaxation, showcasing an inviting atmosphere. A gravel driveway leads up to the entrance, emphasizing the home's accessibility.

Chalet in Round Top

Welcome to the Shangri-La Chalet!

A Chalet-style home in the Catskills, ideal to SKI, HIKE, WORK REMOTELY; PLAY or simply get away. Lots of GAMEROOM activities; a large airy "GREAT ROOM" for gatherings by the FIREPLACE then wander to private bedrooms. OUTDOOR wrap-around split-level DECKS (nearly 3,000 sq. ft!) with all the accoutrements for outdoor GRILLING & DINING AL FRESCO and a dip in the HOT TUB! WIFI is 200 DOWNLOAD /10 UPLOAD On-site AMPLE PARKING Longer stays welcomed & discounted! NOT SUITABLE FOR MINORS.

FamilyKitchenTV

4.96 out of 5 average rating, 127 reviews

The living area features a spacious sofa, accented with patterned throw pillows, placed in front of a wooden coffee table. Sunlight enters through multiple windows, illuminating the room's warm wood floors and green walls. A dining area with natural wood chairs is visible in the background.

Apartment in Round Top

🏔O'Clarke Mountain House - The Catskills

Enjoy a slice of hosts (Bridgitte and Kevin's) ideal Catskill Mountain vacation rental. This 2bd 2ba apartment has an outstanding kitchen, bathrooms, cozy living room, and a perfect dining table to enjoy all your meals. This is our first home, and we will be your neighbors living on the other side of the duplex, we will respect your privacy and let you enjoy your well-earned time away from home. We hope to introduce you to our favorite shops, hikes, and restaurants nearby.

Indoor spacesFamilyLocation

4.99 out of 5 average rating, 176 reviews

A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.

Cabin in Round Top

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

KitchenIndoor spacesPets

4.91 out of 5 average rating, 255 reviews

An open-plan kitchen and dining area features a modern design with green cabinetry and natural wood accents. A wooden dining table is surrounded by four chairs, and large windows allow natural light to fill the space. A ladder leads to a loft area.

Cabin in Catskill

A-Frame w/ Big Yard | 15 min to Hudson, NY

Experience the beauty of the great outdoors while also enjoying modern comforts in this newly renovated A-frame cabin style home. This peaceful location away from the hustle and bustle is still easily accessible without a car and only a 15 minute taxi drive from the nearest station (Hudson Train Station) The elegantly finished interiors continue to be upgraded by the owners who love combining modern touches with the stunning natural surroundings of the area.

FamilyIndoor spacesPets

4.94 out of 5 average rating, 359 reviews

The exterior of a cozy cabin is shown, featuring a wooden deck with a railing and two outdoor chairs alongside a small table. Soft lighting from wall-mounted fixtures complements the greenery surrounding the cabin. Large glass doors invite natural light, enhancing the welcoming ambiance.

Tiny home in Saugerties

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! Ac cools beautifully in summer! The Haven at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

FamilyIndoor spacesAmenities

4.99 out of 5 average rating, 193 reviews

An aerial view captures the serene expanse of the Hudson River, with gently rolling hills and trees framing the water's edge. The property is positioned near the shore, showcasing a mix of gravel and grassy areas leading to the river, inviting a sense of tranquility.

Cabin in Catskill

Riverside Retreat on the Hudson - Modern Cottage

Welcome to the Riverside Retreat on the Hudson, a modern renovated cottage located directly on the Hudson River! Enjoy the beautiful panoramic views from the comfort of the house or in the Adirondack chairs on the patio. Secluded and serene, yet minutes away from downtown Catskill (5 minutes) and Hudson (15 minutes). Hunter and Windham are 30 minutes away for hiking and skiing! We are so excited to share this very special place with you!

FamilyIndoor spacesCheckout

5 out of 5 average rating, 100 reviews

A spacious living area features a large green sectional sofa, complemented by decorative cushions. A flat-screen TV is mounted above a stone fireplace. Large windows provide natural light and views of the surrounding forest, while a coffee table is positioned in front of the seating arrangement.

Cabin in Cairo

The Catskill Equestrian Cabin

Decompress in this beautiful, calm, serene new cabin build nestled in the mountains on a peaceful, private five acre lot, bordering an equestrian center. Walk less than two minutes to see the horses during your stay. The cabin is less than 15 minutes to Windham mountain for winter skiing and under 20 minutes to the popular town of Catskill. This cabin has all the amenities you need for a wonderful stay. We hope to host you soon!

KitchenFamilyTV

4.98 out of 5 average rating, 193 reviews

A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.

Home in Saugerties

The Stone House

The Stone House is a historic house built in 1811 beside the Kaaterskill Creek and surrounded by farmers fields and a beautiful Dutch barn. It's 2 hours from the city at the foot of the Catskill Mountains and a perfect base for exploring the Catskills and the Hudson Valley or for spending quiet weekend in the country.

KitchenIndoor spacesTV

Popular amenities for Round Top family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.82 out of 5 average rating, 109 reviews

A light-filled living room features a plush, curved sectional sofa accompanied by a cozy throw. Natural wood tables and chairs are arranged around a sleek Italian pallet stove, while large windows offer views of the surrounding forest.

Chalet in East Jewett

Modchalet with hot tub and EV-charger

KitchenIndoor spacesGetting around

5 out of 5 average rating, 100 reviews

A dining table is set on a spacious back deck, surrounded by comfortable chairs. The backdrop features vibrant trees and a serene lake, with mountains visible in the distance under a clear blue sky. Natural light enhances the inviting outdoor space.

Cabin in Palenville

Catskills Lake House! Hot Tub, Fire Pit, Game Rm

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 177 reviews

Home in Greenville

Greenville Getaway|Paws & Pines:Dog Park & Hot Tub

FamilyIndoor spacesDecor

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

4.99 out of 5 average rating, 153 reviews

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

KitchenFamilyBathroom

5 out of 5 average rating, 115 reviews

A spacious living area is framed by rustic wooden pillars, featuring a large tan sofa and two green armchairs. A wooden coffee table rests on a light rug, with natural light streaming through a wide window adorned with sheer curtains.

Farm stay in Germantown

Nordic modern getaway on an Alpaca Farm

FamilyKitchenHiking

4.99 out of 5 average rating, 144 reviews

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

KitchenIndoor spacesRiver

4.96 out of 5 average rating, 225 reviews

A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.

Home in Hunter

Modern House with Mountain View @Getawind

KitchenFamilyLocation

4.83 out of 5 average rating, 354 reviews

Container Cabin in the Catskills (Field)

FamilyIndoor spacesComfort

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 103 reviews

A modern living space is highlighted by large windows allowing ample natural light. A cozy sofa is positioned next to a round dining table, with colorful accents and greenery present. Exposed wooden beams add warmth to the open layout, creating a welcoming atmosphere.

Cabin in Hunter

Moritz -Modern Cabin, Stunning Hunter Mtn Views

FamilyIndoor spacesSkiing

4.98 out of 5 average rating, 329 reviews

The blue cottage is framed by colorful autumn foliage, highlighting shades of red, yellow, and orange. The porch features several chairs and a small table. A grassy area leads up to the cottage, situated on a slight elevation, creating a welcoming outdoor space.

Cabin in Tannersville

Cabin by the woods, Hunter Mountain & Kaaterskills

FamilyKitchenCleanliness

4.94 out of 5 average rating, 142 reviews

Cottage in West Camp

Hudson Valley Cottage

FamilyIndoor spacesAccuracy

4.96 out of 5 average rating, 394 reviews

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

Scandinavian Cottage/Mountain Views/Fire pit

Indoor spacesKitchenBathroom

4.98 out of 5 average rating, 100 reviews

A peaceful backyard is featured, showcasing two green swings suspended from a sturdy frame. The grassy lawn is bordered by a wooden fence, and a relaxing seating area with a lounge chair is visible in the background, surrounded by greenery and trees.

Home in Catskill

Catskill Village Ski Hike Lake Pet Main St Pool

Indoor spacesKitchenCheck-in

4.92 out of 5 average rating, 144 reviews

An inviting outdoor space features a wooden dining table surrounded by natural wicker chairs. Soft lighting illuminates the area, highlighting a cozy seating arrangement with cushions. Dense woods create a serene backdrop, enhancing the peaceful atmosphere as the evening sky darkens.

Cabin in East Jewett

The Garden House - Private, Secluded, & Mt Views!

Indoor spacesKitchenSleep quality

4.97 out of 5 average rating, 226 reviews

A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.

Home in Catskill

Cheerful Catskill Village Cottage

KitchenIndoor spacesComfort

4.98 out of 5 average rating, 191 reviews

A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.

Home in Cornwallville

Private Waterfall Retreat on 10 acres

FamilyIndoor spacesCheckout

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 219 reviews

A large kidney-shaped pool reflects the clear blue sky, bordered by a spacious patio area. The two-story brick home with teal doors and large windows is visible in the background, surrounded by lush greenery and a fence for added privacy.

Chalet in Catskill

Daydream Mountain Art-Chateau | Hot Tub & Pool

KitchenIndoor spacesPets

4.94 out of 5 average rating, 398 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

FamilyKitchenGrill

4.98 out of 5 average rating, 124 reviews

Chalet in Elka Park

Thorne Hollow - Mountain Getaway with Pool+HotTub

KitchenFamilyLocation

4.89 out of 5 average rating, 376 reviews

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

Home in Ghent

Modern Barn on 12 acres w Sauna, FirePit+swimming

Indoor spacesFamilyHiking

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

Indoor spacesKitchenHiking

4.95 out of 5 average rating, 247 reviews

A seasonal saltwater pool is surrounded by a wooden deck and lounge chairs, offering a scenic view of the lush hillside. An umbrella provides shade, and a basketball hoop is positioned at one end of the pool, enhancing outdoor leisure options.

Cabin in Shandaken

Catskills Retreat | Heated Pool & Hot Tub

Indoor spacesKitchenBathroom

5 out of 5 average rating, 172 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

FamilyIndoor spacesShared spaces