Family-friendly holiday rentals in Round Top

4.99 out of 5 average rating, 112 reviews

Home in East Durham

Pawfect Family Retreat w/fenced-in yard & Dog Park

Welcome to the Pawfect Family Retreat- our dog-focused cottage in East Durham, NY! This cozy 2BR, 1BA home with a loft (3rd BR /sleeping area) is made for tail wags and happy hearts. Enjoy a fully fenced backyard with a private dog park, pup-friendly amenities, and cozy spaces for the whole family. Just minutes to Zoom Flume. Close to Windham(13 mi) & Hunter Mountain(18 mi), hiking, farms, breweries, and antique shops, town of Catskill & Hudson-your year-round getaway for unforgettable memories.

FamilyIndoor spacesCheck-in

5.0 out of 5 average rating, 148 reviews

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.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Indoor spacesKitchenComfort

Superhost

A cabin nestled among tall trees is gently illuminated at dusk. Soft light streams through the open sliding door, revealing a cozy sleeping area with a person resting on a bed. The surrounding forest is lush with greenery, enhancing the serene atmosphere.

Cabin in Saugerties

4.86 out of 5 average rating, 348 reviews

40-Foot Container Cabin in the Catskills

*Click our logo to see the NEW DOUBLE container Cabin 1: a 2 bed/2 bath luxury retreat! Cabin 2 is our RECENTLY renovated 40-foot container cabin - with a full bathroom, A/C, and wood-fired hot tub - set on a waterfall and 20 acres of wilderness. Warm in winter and cool in the summer, enjoy the deck, fire ring, grill, and hammock. The cabin is two hours north of NYC, with a refrigerator, Wifi, propane, furnace, and wood stove. Woodstock, Kingston, the Hudson River and hiking trails 15 min away.

Indoor spacesFamilyAccess

Superhost

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

4.93 out of 5 average rating, 277 reviews

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.

FamilyIndoor spacesBreakfast

4.96 out of 5 average rating, 115 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 spacesLayout

4.97 out of 5 average rating, 166 reviews

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.

Cabin in Saugerties

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.

KitchenIndoor spacesOutdoor spaces

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.

FamilyIndoor spacesDecor

4.94 out of 5 average rating, 344 reviews

A modern A-frame cabin is illuminated under the evening sky, featuring large glass doors that open to a spacious deck with outdoor seating. The surrounding wooded area is visible, adding to the tranquil setting of the nature retreat.

Cabin in Freehold

Tiny Home A-Frame with Hot Tub & Creek

Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our brand new home has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to WFH.

Indoor spacesKitchenLong stay

4.98 out of 5 average rating, 210 reviews

A single-story cottage is set amidst lush greenery, featuring a welcoming porch and large windows. A stone pathway leads to the entrance, surrounded by well-maintained grass and shaded by surrounding trees.

Guest house in Cairo

Tomte Cottage in the Catskills!

Stay in the heart of the Catskills! 2 Bedroom Cottage with private entrance. One bedroom has a queen bed the other a twin/full bunk bed, suited for up to 5 guests! Cottage has full kitchen and bath w/shower. Wi-Fi and a 50 inch smart tv. Located 18 minutes to Windham and 30 to Hunter for skiing or snowboarding. Whether you are looking for a quiet weekend retreat or family weekend skiing trip, hiking or just exploring, this is the place for you! Self check in for your convenience.

KitchenIndoor spacesSleep quality

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.

Flat 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.

FamilyIndoor spacesWifi

4.99 out of 5 average rating, 174 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.

KitchenFamilyOutdoor spaces

4.91 out of 5 average rating, 254 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.

Indoor spacesFamilyHiking

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

4.99 out of 5 average rating, 143 reviews

Home in East Jewett

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

Indoor spacesKitchenCheck-in

The exterior of the house is surrounded by mature trees, with a spacious deck featuring lounge chairs and a hammocks for relaxation. A grill is visible, suggesting options for outdoor cooking and entertaining.

4.95 out of 5 average rating, 253 reviews

Catskill Mountain House 🌄

KitchenFamilyWalkability

4.99 out of 5 average rating, 102 reviews

A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.

Home in Accord

Accord River House

Indoor spacesKitchenCheck-in

A wooden house is set against a wooded backdrop, featuring a dark facade with large windows. An outdoor fire pit is surrounded by seating arrangements on either side. The grassy area offers a natural and open invitation to enjoy the surrounding landscape.

4.96 out of 5 average rating, 124 reviews

Modern High-end 2BR2BATH in the woods of Catskills

KitchenIndoor spacesSleep quality

4.95 out of 5 average rating, 507 reviews

An aerial view captures the chalet, surrounded by a lush, open green lawn. Trees line the property, providing a natural border. The distant mountains and hills are visible, with a gentle gradient of colors as sunset approaches, suggesting a serene rural setting.

Cabin in Windham

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)

KitchenIndoor spacesBiking

4.96 out of 5 average rating, 222 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

Indoor spacesFamilyAccuracy

4.95 out of 5 average rating, 109 reviews

A vibrant yellow hammock is positioned among trees in a lush green yard. The scene captures a person reading, with a portion of a spacious wrap-around deck visible in the background, along with outdoor seating arranged nearby.

Cabin in Tannersville

Hot Tub~Fire Pit~Hiking~BBQ~Catskills~Kaaterskills

KitchenFamilyAmenities

Superhost

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

4.82 out of 5 average rating, 109 reviews

Modchalet with hot tub and EV-charger

FamilyKitchenValue

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 140 reviews

Cottage in West Camp

Hudson Valley Cottage

Indoor spacesKitchenView

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.

4.97 out of 5 average rating, 225 reviews

Cheerful Catskill Village Cottage

FamilyIndoor spacesComfort

4.99 out of 5 average rating, 547 reviews

A modern bungalow is illuminated at dusk, featuring large glass doors that reveal a warm interior. A spacious deck area is adorned with string lights and includes comfortable seating options, inviting relaxation amid the surrounding trees.

Bungalow in Cairo

Modern Riverfront, Swim & Fish, 20 min to Hudson

FamilyIndoor spacesAccuracy

4.91 out of 5 average rating, 189 reviews

The treehouse is elevated among lush green trees, showcasing a blend of wood and natural surroundings. A spacious deck extends from the structure, while a nearby wooden railing provides safety. The entrance features a single door with a window above, enhancing natural light.

Treehouse in Palenville

Cozy Treehouse in Catskill Mountains.

Indoor spacesFamilyPets

4.93 out of 5 average rating, 867 reviews

Cabin in Woodstock

Byrdcliffe Artist Studio (27.1-1-70)

KitchenIndoor spacesLayout

4.97 out of 5 average rating, 149 reviews

Cottage in Elka Park

The North Nook-Mtn Views, 5 min to downtown,hiking

FamilyKitchenWifi

4.92 out of 5 average rating, 158 reviews

The living area features a light-colored sofa and a woven area rug, creating an inviting atmosphere. A plaid armchair sits alongside a sleek coffee table, and a large artwork depicting natural scenery adorns one wall. A ceiling fan contributes to the airy ambiance.

Cottage in Catskill

Redwood Lodge - Cottage w/ Sauna & Fireplace

Indoor spacesKitchenGrill

4.99 out of 5 average rating, 379 reviews

A modern tiny house is framed by lush greenery, featuring a wooden exterior and large windows that invite natural light. A spacious deck with a full-size dining table is visible, surrounded by a well-maintained landscape of plants and grass.

Tiny home in Saugerties

Modern Catskills Cabin

Indoor spacesFamilyBack garden

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 375 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

FamilyIndoor spacesBiking

4.97 out of 5 average rating, 143 reviews

A sparkling heated pool is framed by natural surroundings, with a stand-alone guest house visible in the background. Lush trees create a serene atmosphere, enhancing the privacy of the outdoor space. Nearby, seating areas and open grass provide inviting spots for relaxation.

Cottage in Bearsville

Contemporary Guesthouse with Heated Pool

Indoor spacesFamilyBathroom

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

Indoor spacesFamilyBack garden

4.99 out of 5 average rating, 373 reviews

The interior space showcases exposed timber beams and a warm wood palette. A comfortable seating area is highlighted by a vibrant patchwork rug, while a staircase leads to the upper level. Shelving units display books, and a television is mounted on the wall.

Cottage in Woodstock

Grapevine Cottage

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 124 reviews

Chalet in Elka Park

Thorne Hollow - Mountain Getaway with Pool+HotTub

KitchenFamilyHiking

4.93 out of 5 average rating, 120 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

Summer Paradise - Pool, Fire-pit, Nursery!

KitchenIndoor spacesWifi

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.

4.98 out of 5 average rating, 100 reviews

Catskill Village Ski Hike Lake Pet Main St Pool

KitchenFamilyCheck-in