Holiday houses in Round Top

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Top-rated holiday rentals in Round Top

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The charming cabin features a spacious front porch with wooden rocking chairs and decorative string lights. A well-maintained yard surrounds the structure, with green grass and flowering plants. The cabin's wood exterior blends harmoniously with the natural landscape of trees and open sky.
Cabin in Catskill
4.88 out of 5 average rating, 110 reviews

Cozy Cabin w/ 10 Min Walk to Downtown Catskill

Take a deep breath and relax after a long hike through the Catskill Mountains, a swim in local mountain streams or a skiing trip upstate. Leave your worries behind and take in nature and local scenery as you get quality rest in this cabin. This cabin is central to everything including hiking, skiing, whitewater rafting and more in the heart of Catskill Mountains. You'll be within 30 minutes of the central point of many Catskill's attractions including Hunter Mountain, Kaaterskill Falls & more.

Top Guest favourite
The farmhouse exterior features a spacious porch with steps leading down to a grassy area. The surrounding landscape includes trees, providing a natural setting. Large windows allow for plenty of natural light, enhancing the home's open feel.
Home in Saugerties
4.92 out of 5 average rating, 277 reviews

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!

Top Guest favourite
A well-lit bedroom features a spacious bed adorned with patterned pillows and a textured throw. A simple stool stands beside the bed. Bookshelves filled with collectibles and a decorative arrangement are visible. Multiple windows allow natural light to fill the room, enhancing its cozy atmosphere.
Apartment in Catskill
4.98 out of 5 average rating, 417 reviews

Main St. Steps to everything. Comfort & Design.

Relax in your own spacious and private light-filled retreat. Enjoy our cozy and unique space filled with art, vintage and antique finds, collectibles, ceramics, and books. Escape or stay connected with excellent hi-speed internet. Fully stocked kitchen for all your needs. Dedicated off-street parking. Steps to all Catskill has to offer in Restaurants, Breweries, Shops and Culture. Minutes to 3 beautiful preserves, the Hudson and Catskill Creek. 15 minutes to Hudson. 30 min. to Kaaterskill Falls.

Top Guest favourite
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
4.97 out of 5 average rating, 185 reviews

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

Top Guest favourite
A living area features a comfortable sectional sofa adorned with cushions and a low wooden coffee table. Natural light fills the space through two windows, while a floor lamp provides additional illumination. The interior is accented by warm, earthy tones and wooden flooring.
Apartment in Stone Ridge
4.92 out of 5 average rating, 559 reviews

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Top Guest favourite
A pass-through window features a wooden countertop, displaying decorative items and a candle. A vibrant blue refrigerator and various kitchen appliances are visible in the background. The space is brightened by natural light, creating a cheerful ambiance.
Cottage in Catskill
4.96 out of 5 average rating, 308 reviews

1930's Cottage charm cozy air cond. near hiking

1 bedroom 1930's guest cottage with a living room. Near many hiking trails. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.

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, 104 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!

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, 109 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.

Top Guest favourite
A charming cottage is set in a snowy landscape, surrounded by tall trees and quiet woods. Warm light glows from the windows, contrasting with the white snow covering the ground. A wooden staircase leads to the entrance, enhancing the inviting winter scene.
Home in Catskill
4.99 out of 5 average rating, 207 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

Athens, NY Entire House - 1 bedroom Quiet Country setting Winter time is a great time to escape to upstate NY. Guests have called it "a very cozy cottage in the woods". It is set back off the road and a great place to get away and unwind. 10 minutes from Exit 21 on the NYS Thruway and is an easy drive to several towns on the Hudson River. They are known for their restaurants, local shops and quaint downtowns. Area features outdoor activities: hiking trails, skiing and kayaking.

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, 115 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, 330 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 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
4.98 out of 5 average rating, 120 reviews

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.

Popular amenities for Round Top holiday rentals

When is the best time to visit Round Top?

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Avg. price$410 AUD$422 AUD$410 AUD$385 AUD$369 AUD$419 AUD$419 AUD$427 AUD$421 AUD$361 AUD$421 AUD$477 AUD
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Frequently Asked Questions

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

    Four-legged friends are welcome in Round Top. Choose from more than 30 vacation rentals for guests traveling with pets.

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

    Experience the best of Round Top with our house rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

    Yes! Work meets play with ease at over 30 vacation rentals in Round Top featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Round Top have wifi?

    Absolutely! We offer over 20 house 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.

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

    Round Top has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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 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.

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 $194 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,290 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 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, Wi-Fi 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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