Family-friendly holiday rentals in Round Top

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

Welcome to The Lakeside Lodge. Your lake house escape in the Catskill mountains. Hidden near the end of a private road are 2 acres of peaceful serenity surrounded by trees, wildlife & a swimmable lake. Our cabin is a wonderful retreat for friends & families to gather, play, relax & recharge among the beauty of nature. Highlights include a hot tub for 7, full kitchen, game room, 2 fireplaces & full bar. Near skiing, hiking, biking, farms & villages, but you may not want to leave the house. ;-)

Beautiful farmhouse with Mountain View- HITS- AC

Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

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!

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.

Daydream Mountain Art-Chateau | Hot Tub & Pool

Perched on a hill, with a rare Catskill Mountain view, our home is a special nature escape. Designed for relaxing, creativity, and fun. It's perfect for hiking, swimming, skiing, and exploring. A short drive to Catskill Town, Hudson, Woodstock, and other beautiful towns. Stocked with instruments, toys, books, games, a ping-pong table, and basketball. Great for families and friends. Enjoy the 50 ft. pool during the Summer or soak in the hot tub all year-round, you're in for a magical stay!

🏔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.

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.

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.

Greenville Getaway|Paws & Pines: Dog Park & HotTub

Welcome to Greenville Getaway | Paws & Pines- where dogs might have more fun than their humans! 🐾🌲 With a fully fenced yard + private dog park, your pup can run, sniff & zoom off-leash while you relax. Discover the Ball Library 🎾, agility fun & Happy Tails Boutique 🐶🛍️, while humans enjoy the hot tub + arcade game room. Tucked in the Catskills and made for dogs at heart, because here, your dog isn’t joining your vacation… you’re joining theirs!

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!

Lux Modern Cabin at Hunter Mountain

Modern private retreat in the heart of the Catskills with expansive views of Hunter Mountain that delivers an ultra-lux getaway experience. Casa Nevana is a brand-new construction. Enjoy each season of the Catskills in comfort and style. Immerse yourself in nature and slow living while experiencing luxurious accommodations and impeccable design. Follow us on IG @CasaNevana to see more of the home, local hot spots and more!

Schoolhouse in the Catskills

✨ Renovation Note (2025): We’re thrilled to share that the Schoolhouse has just completed a major renovation! Our home is now 4 bedrooms and 4 bathrooms (formerly 2 and 2), with a brand-new attic play space for kids and a dishwasher in the kitchen. Washer and dryer are now accessible in the renovated basement. *FOR SKIERS: 20 minutes to Hunter, 25 minutes to Wyndham!