
Vacation rentals in Round Top
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Top-rated vacation rentals in Round Top
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Popular amenities for Round Top vacation rentals
Other great vacation rentals in Round Top

Cozy Mountain Cabin Near Windham Slopes
Impressed by the attention to detail! Communication was seamless! The host was responsive and considerate, ensuring our stay was comfortable from start to finish The host stocked the kitchen with essentials. Highly recommend to anyone looking for a cozy and clean place to stay!

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
This place was perfect for our Mom’s Book Club Retreat. The living room was spacious enough for all 7 of us but still so cozy for chatting and reading (we were looking at tags to buy the same couches). The weather was terrible so we didn’t get to enjoy the outdoor spaces as much as we’d like but the hot tub and fire pit were great. The kitchen had everything we needed to cook all our meals . Communication and check in were a breeze. Would definitely recommend this place!

Perfect Windham & Hunter Ski House 2 Miles to Mntn
One of the best Airbnbs I've stayed at. The house is amazing - spacious, cozy, ad each room had their own temperature control! Plenty of communal space and the kitchen was very functional. The hosts were so responsive and nice and even offered to mail a piece of clothing we had left at the house afterwards. Definitely would come back again and highly recommended.

Private Mountain Lodge, 10mins to Hunter & Windham
My family's second visit to this beautiful gem overlooking the mountains and frozen pond. Our hosts are highly communicative and helpful. The description is accurate. Considering our 2nd visit and rebooked for 3rd in 2026 - this speaks volumes -- more than meets our needs, well stocked. We're looking forward to visiting during the summer months to further appreciate the views. Grateful to them for sharing their home with us.

Lake house with arcade games
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.

A Place Called Home in The Catskill
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!

Luxury Spacious Private Home w/tub! Enjoy Spring
It’s a fantastic place to stay—a well-designed, private home with a great layout. Conveniently located near the mountain, it’s perfect for skiing while still offering a peaceful retreat.

Sauna equipped Belleayre Cozy Cabin
Perfect for a ski weekend. Sauna is great, and location cannot be beat.
Quick stats about vacation rentals in Round Top
Total rentals
50 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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 $120 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 10 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 cabin rentals in Round Top have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Round Top. Enjoy a tailored experience with all the comforts you desire.
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- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Minnewaska State Park Preserve
- Taconic State Park
- John Boyd Thacher State Park
- Zoom Flume
- Bousquet Mountain Ski Area
- Opus 40
- Howe Caverns
- Otis Ridge
- Bash Bish Falls State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Thaddeus Hait Farm
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Huck Finn’s Playland, Albany
- Plattekill Mountain
- Canterbury Farm
- Naumkeag
- Berkshire Botanical Garden
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