
Holiday rentals 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.

Athens, NY House - 1 Bedroom "Want to Get Away"?
Athens, NY Entire House - 1 bedroom Quiet Country setting Spring 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,snowboarding and kayaking.

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.

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.

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!

Mystical Moon Retreat near Woodstock, NY
Situated on the crystalline Plattekill Creek, this secluded paradise is located 6 miles from Woodstock, NY. It is nestled in enchanted woods, steps away from a private swimming hole. Lounge on the porch by the babbling creek, sip hot cocoa under the stars. The Moon Shala is a magical separate small unheated building, a perfect sanctuary for anyone looking to unwind and relax in the warmer months. A 4-wheel drive vehicle is a must in the colder months. One pet is welcome for an additional fee.

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.

D & D’s Place
The home is located in "CATSKILL PARK", only five mile away from the #1 most visited state park in New York, "NORTH SOUTH LAKE" where you can camp, picnic, hike, swim, sail, canoe, kayak or just experience the beautiful view of the "CATSKILL MOUNTAINS". The apartment is very spacious, secluded and safe with plenty of room for children to play. We have enjoyed this area most of our life's and have raised our kids up here, so I am sure you will too! We have 2 lovable pups that live on site.

Idyllic Mountain view Catskills home near Windham
Nestled in the mountain, this beautiful three bedroom home has character galore, from the covered front porch to the birch log handrails leading to the loft. The views are bucolic; out the back is the Catskill Mountain range, and out the front is the Helderbergs. This is a very desirable location, only 15 minutes from Ski Windham. There are cathedral ceilings in the living room and dining room, and exposed beams in the large kitchen. The skylights and large windows bring the outside in.

The Kaaterskill Cottage - views of Hunter Mtn!
Enjoy the serene environment of the Catskills from our recently renovated 1910 cottage. Our home offers privacy, comfort, and convenience in a prime location for anyone looking to explore. We are located less than a half mile to Kaaterskill Falls, and nearby to great hiking and skiing destinations. Our space has been set up with love and attention to detail, comfortably sleeps 6 adults and is family friendly. We welcome you to our cozy cottage in the mountains - make yourself at home!

🏔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.

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

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
Other great holiday rentals in Round Top

Enchanting Cabin with fireplace views and trails

Cabin on 2.5 Acres w/ Firepit & Indoor Jacuzzi Tub

Chic Stream-side Chalet • Mountain View • Catskill

The Pine Tree Chalet | Perfect Airbnb in Catskills

Rhinebeck Lakefront Private Retreat

Special: Pond Views, Backyard Dining+BBQ.

Cozy Cabin in the Catskills - #1

Woodland Spring Retreat at the Red Door Cabin
When is the best time to visit Round Top?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 237 | € 244 | € 237 | € 222 | € 213 | € 242 | € 242 | € 246 | € 243 | € 237 | € 246 | € 270 |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
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 € 112 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
50 of Round Top holiday rentals include wifi 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!
Destinations to explore
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- June Farms
- Naumkeag
- Benmarl Winery
- Berkshire Botanical Garden
- Millbrook Vineyards & Winery




