
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.

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.

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.

1930's Cottage charm fireplace, close to skiing
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.

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!

Hideaway Windham/Hunter Fireplace, Snow & Skiing
Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

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.

🏔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.

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!

Riverfront, Fireplace, 20 min to Hudson & Windham
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.

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.

b/w Hudson&Hunter, a Catskill Unit Made for Snugs
Welcome to the Catskills and rest up in this calm, small, and stylish space! We recently rebuilt the entire interior of an old brick building and imagined the first floor (*** the entrance is at the back of our house***) as a guest unit for our friends & family during visits. When we do not have friends & family visiting, we are offering this space to you! We are architects by training and have placed our aesthetic energy in making this unit modern but also cozy.

Modern A-Frame Cabin with Loft, Firepit and Grill
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.
Popular amenities for Round Top holiday rentals
Other great holiday rentals in Round Top

Lovely Centennial Cottage Apartment

Moritz -Modern Cabin, Stunning Slope Views

Enchanting Cabin with fireplace views and trails

Cabin Retreat w/ Firepit & Indoor Jacuzzi Tub

Modern Cabin in the woods

Winter Special: Pond Views, Backyard Dining+BBQ.

Cozy Cabin in the Catskills - #1

Red Door Cabin, cozy winter escape
When is the best time to visit Round Top?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 236 | € 243 | € 236 | € 222 | € 212 | € 242 | € 242 | € 246 | € 242 | € 208 | € 242 | € 275 |
| 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 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 cabin rentals in Round Top?
Experience the best of Round Top with our cabin 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 house rentals in Round Top have free parking?
Absolutely! We offer over 20 house 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 € 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!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Minnewaska State Park Preserve
- Windham Mountain
- Catamount Mountain Ski Resort
- John Boyd Thacher State Park
- Howe Caverns
- Bash Bish Falls State Park
- Kent Falls State Park
- Hunter Mountain Resort
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Zoom Flume
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Benmarl Winery
- Millbrook Vineyards & Winery




