Holiday houses in Round Top

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Top-rated holiday rentals in Round Top

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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
5 out of 5 average rating, 113 reviews

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!

Top Guest favourite
A spacious retreat is seen from above, featuring a large deck with seating and modern design elements. Surrounding foliage displays vibrant autumn colors, while a gravel pathway leads to the house. The serene landscape emphasizes the property's natural setting.
Home in Round Top
4.97 out of 5 average rating, 220 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

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
4.94 out of 5 average rating, 268 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.

Top Guest favourite
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
4.98 out of 5 average rating, 299 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Guest favourite
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
4.96 out of 5 average rating, 109 reviews

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!

Guest favourite
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
4.96 out of 5 average rating, 216 reviews

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.

Top Guest favourite
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
4.94 out of 5 average rating, 316 reviews

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.

Top Guest favourite
A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.
Home in Cementon
4.95 out of 5 average rating, 234 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Top Guest favourite
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
4.97 out of 5 average rating, 135 reviews

Luxury A-Frame Cabin in the Woods with Sauna

Modern, glass‑fronted A‑frame perched in the Catskills, offering sweeping mountain vistas. Relax in the private cedar barrel sauna & refreshing outdoor shower, gather round the smokeless propane fire-table, or fire up the propane grill for al‑fresco dinners. A stylish bedroom with woodland views, luxe linens, fast Wi‑Fi, and a cozy electric fireplace blend comfort with design. Minutes to trailheads, waterfalls & farmers markets - ideal for couples seeking a serene and restorative escape.

Guest favourite
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
4.97 out of 5 average rating, 119 reviews

🏔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.

Top Guest favourite
A cozy seating area features a large, woven hanging chair with a white cushion and a bright green accent pillow. A textured pouf and a small side table complement the space, which is surrounded by large windows offering views of the mountains and natural light.
Apartment in Freehold
5 out of 5 average rating, 344 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

Top Guest favourite
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
4.99 out of 5 average rating, 522 reviews

Modern Riverfront, Swim & Fish, 20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Popular amenities for Round Top holiday rentals

When is the best time to visit Round Top?

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Avg. price$479 NZD$493 NZD$479 NZD$449 NZD$430 NZD$489 NZD$489 NZD$498 NZD$491 NZD$479 NZD$496 NZD$545 NZD
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Frequently Asked Questions

  • Are there family-friendly house rentals in Round Top?

    Round Top has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Round Top?

    Experience the best of Round Top with our cabin rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly house rentals in Round Top?

    Four-legged friends are welcome in Round Top. Choose from more than 10 house rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Round Top?

    Yes! Work meets play with ease at over 20 house rentals in Round Top featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Round Top have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Round Top. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Round Top have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Round Top. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Round Top have wifi?

    Absolutely! We offer over 10 cabin rentals with wifi in Round Top. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Round Top have free parking?

    Absolutely! We offer over 10 cabin rentals with free parking in Round Top. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Round Top

  • Total holiday rentals

    Explore 50 holiday rentals in Round Top

  • Nightly prices starting at

    Round Top holiday rentals start at $226 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Round Top holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Round Top rentals

  • 4.9 Average rating

    Round Top stays are highly rated by guests—averaging 4.9 out of 5!

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