Best Vacation Homes in Round Top
Cabin
9.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
750 ft²
Fireplace/Heating
Pet Friendly
Kitchen
Parking
AU $379/Night
7 Nights - AU $2,656
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
2002.09 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
Internet
AU $738/Night
7 Nights - AU $5,163
Hotel
9.0(100 Reviews)
1 Bath
Pool
Balcony/Terrace
Breakfast- Parking
AU $313/Night
7 Nights - AU $2,193
House
10.0(32 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $378/Night
7 Nights - AU $2,649
Resort
9.0(45 Reviews)
2 Baths
9 Guests
236.81 ft²
Private Pool
Skiing- Fireplace/Heating
- Pool
AU $182/Night
7 Nights - AU $1,275
House
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $694/Night
7 Nights - AU $4,860
House
10.0(8 Reviews)
5 Bedrooms
3 Baths
14 Guests
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $1,408/Night
7 Nights - AU $9,859
House
10.0(8 Reviews)
5 Bedrooms
3 Baths
15 Guests
3500 ft²
- Private Pool
Hot Tub- Fireplace/Heating
- Pool
AU $964/Night
7 Nights - AU $6,745
Round Top Luxury Rentals
Villa
9.0(6 Reviews)
6 Bedrooms
7 Baths
15 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
AU $1,375/Night
7 Nights - AU $9,623
House
5 Bedrooms
3 Baths
14 Guests
64.58 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
View
AU $1,230/Night
7 Nights - AU $8,609
House
10.0(3 Reviews)
5 Bedrooms
3 Baths
10 Guests
4200 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $880/Night
7 Nights - AU $6,158
House
9.8(26 Reviews)
3 Bedrooms
3 Baths
11 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $803/Night
7 Nights - AU $5,622
House
3 Bedrooms
2 Baths
8 Guests
1550 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
AU $663/Night
7 Nights - AU $4,640
House
10.0(2 Reviews)
3 Bedrooms
1 Bath
10 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $655/Night
7 Nights - AU $4,587
Cabin
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $623/Night
7 Nights - AU $4,358
House
10.0(4 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
AU $576/Night
7 Nights - AU $4,032
Round Top Pet Friendly Vacation Rentals
House
8.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
AU $488/Night
7 Nights - AU $3,418
House
8.3(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
753.47 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
AU $437/Night
7 Nights - AU $3,058
Cabin
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
Air Conditioner- Internet
AU $350/Night
7 Nights - AU $2,452
Other
9.7(3 Reviews)
1 Bedroom
1 Bath
6 Guests
495.14 ft²
- Pet Friendly
- Parking
Child Friendly
AU $217/Night
7 Nights - AU $1,520
House
9.4(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Spa
- Breakfast
- Pet Friendly
- Air Conditioner
AU $296/Night
7 Nights - AU $2,068
Villa
8.0(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $462/Night
7 Nights - AU $3,237
House
2 Bedrooms
2 Baths
6 Guests
1800 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
AU $307/Night
7 Nights - AU $2,150
RV Rental
5.0(2 Reviews)
1 Bedroom
1 Bath
6 Guests
500 ft²
- Pet Friendly
- Child Friendly
AU $193/Night
7 Nights - AU $1,354
Round Top Large Vacation Homes
Other
10.0(1 Review)
5 Bedrooms
2 Baths
10 Guests
3300 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
AU $1,037/Night
7 Nights - AU $7,258
Villa
3 Bedrooms
2 Baths
8 Guests
1496.18 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
AU $420/Night
7 Nights - AU $2,943
House
3 Bedrooms
2 Baths
10 Guests
1550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $1,226/Night
7 Nights - AU $8,582
House
4.8(19 Reviews)
6 Bedrooms
4 Baths
10 Guests
3700 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $1,062/Night
7 Nights - AU $7,436
Bed & Breakfast
7.3(28 Reviews)
6 Bedrooms
1 Bath
16 Guests
- Hot Tub
- Breakfast
- Pet Friendly
- Parking
AU $216/Night
7 Nights - AU $1,511
Why Choose Rent By Owner for your Round Top Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Round Top
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you enjoy the region's unique charm and serene atmosphere, making your stay in this destination truly memorable.
Peak Season Highlights
Summer (June to August)
During the summer months, the region experiences warm weather perfect for outdoor activities and exploring local scenery.
Average Temperature Daytime: around 80°F to 85°F - Nighttime: around 60°F to 65°F
Fall (September to October)
Autumn is a popular time when the area showcases vibrant foliage, attracting visitors seeking scenic drives and outdoor events.
Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 50°F to 55°F
Off-Season Highlights
Spring (April to May)
Spring offers milder temperatures and blooming landscapes, making it an ideal time for quieter visits and nature walks.
Average Temperature Daytime: around 60°F to 70°F - Nighttime: around 40°F to 50°F
Winter (December to February)
In winter, the area tends to be less crowded, providing a peaceful retreat with chances for cozy getaways amid cooler temperatures.
Average Temperature Daytime: around 30°F to 40°F - Nighttime: around 20°F to 25°F
Weekly Weather Forecast for Round Top
How to Book Your Round Top Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Round Top
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor grilling with a fully-equipped barbecue area to make the most of your stay here.
- Relax in a spacious backyard or garden, perfect for outdoor leisure and family gatherings.
- Take advantage of nearby walking trails or nature paths that showcase the natural beauty of this region.
- Make use of an outdoor fire pit to unwind under the stars after a day exploring the area.
- Benefit from access to scenic patios or decks that provide stunning views of the surrounding landscape.
- Experience the convenience of available parking for outdoor recreational gear such as bikes or kayaks.
- Some properties may include private pools or hot tubs to enhance your outdoor relaxation in this destination.
Top Attractions Around Round Top
What attractions are nearby?
In this charming destination, you can explore a variety of outdoor activities and local attractions that showcase the natural beauty and cultural heritage of the area, making your stay truly memorable.
Family Activities
- Explore the Hudson River: Enjoy a family-friendly day of kayaking or paddleboarding along the scenic waters, perfect for creating memorable outdoor adventures here.
- Visit local farms and orchards: Engage in seasonal fruit picking and learn about regional agriculture at the area's charming farms, ideal for a fun family outing.
- Discover nearby hiking trails: Venture into the surrounding natural landscapes on well-maintained trails suitable for all ages, offering breathtaking views and fresh air.
- Attend community festivals and events: Immerse your family in local culture through seasonal festivals that showcase regional arts, music, and cuisine in the area.
Adult Activities
- Hiking and Nature Walks: Explore scenic trails that showcase the natural beauty of this region, ideal for enjoying an active day amidst lush landscapes.
- Local Art Galleries and Studios: Discover the vibrant arts scene here by visiting unique galleries and studios that highlight regional artists' creativity.
- Farmers’ Markets and Food Tours: Delight in authentic flavors by sampling fresh produce and local delicacies at nearby farmers' markets or food tours in the area.
- Historic Sightseeing: Immerse yourself in the area's history by exploring charming historic sites and landmarks that tell the story of this destination.
Other Places to Stay in Round Top, NY
Blackhead Mountain Country Club
Round Top Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Keep an eye on the area’s event calendar to align your stay with local festivals or markets, enhancing your experience here.
- Choose the Perfect Accommodation: Select a well-rated vacation rental in this destination that offers convenient access to the region's charming attractions and natural beauty.
- Explore Off-the-Beaten-Path Spots: Venture beyond the typical highlights to discover hidden gems nestled around here, making your visit truly unique.
- Pack Thoughtfully: Bring essentials suitable for this destination’s climate and activities, ensuring you’re comfortable whether exploring outdoors or relaxing indoors.
Transportation Options
- Driving Your Own Vehicle: Navigating by car offers the flexibility to explore nearby attractions and enjoy the scenic countryside of this region at your own pace.
- Regional Bus Service: Public bus routes connect here to larger cities, providing an economical way to travel without the hassle of parking or navigating busy streets.
- Local Taxi and Ride-Sharing Services: Convenient for quick trips within the area or to nearby transportation hubs, ensuring you stay mobile during your stay.
- Nearby Airport Access: The closest airports provide options for flying in from major cities, with ground transportation available for seamless transfers to your vacation rental here.
Local Customs Options
- Local Craftsmanship: You’ll notice a strong appreciation for handmade and locally crafted goods that reflect the region’s unique artistic heritage.
- Traditional Food Customs: Dining in this area often involves enjoying farm-to-table dishes rooted in historic recipes and seasonal ingredients.
- Festivals and Celebrations: Participating in community festivals offers insight into the region’s vibrant cultural traditions and lively social gatherings.
- Respect for Nature: There is a deep-seated reverence for the natural environment, which influences outdoor activities and conservation-minded practices here.
Frequently Asked Questions About Round Top?
1. What are the top vacation rentals in Round Top?
There are a lot of options in Round Top. If you plan on staying in the Round Top area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Round Top:
- Round Top: scenic , serene, beautiful.roomy
- Stylish Catskills Retreat: Year-Round Adventure!
- Catskills Escape! Hot Tub, Massage Chairs & Games
- Quiet Mountain View Art House - Up on a hill - Round Top!
- Cottage w/hot tub 15min to Windham & Catskill
- Mountain retreat in heart of the Catskills
- Welcome to the Shangri-La Chalet in The Catskills! Longterm rentals welcomed
- Stylish Catskills Retreat: Year-Round Adventure!
- The Pine Tree Chalet: Perfect Getaway in Catskills
- Private Catskills Getaway with Gorgeous Mountain View’s
2. Which vacation homes in Round Top are best for families?
If you are looking for a family-friendly vacation home in Round Top, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Round Top:
3. How many Rentbyowner vacation rentals are available in Round Top?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 36 in the Round Top area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Round Top.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property, so it is important to review the specific listing details or contact the owner directly to understand the terms and any applicable fees before booking.
5. How do I best communicate with the property owner during my stay?
Most hosts provide contact information within the listing. You can reach out through the messaging platform on the booking site to ask questions or coordinate your arrival and check-in details.
6. Are there any additional fees I should be aware of when booking here?
Additional charges such as cleaning fees, service fees, or taxes are typically listed in the property's details. It’s advisable to read the full listing or ask the owner directly for clarity.
7. What amenities are usually included in vacation rentals in this region?
Amenities can vary but often include essentials like Wi-Fi, heating or cooling, kitchen facilities, and parking. Check each listing for a detailed list of what’s included in your selected property.
8. Is there a minimum stay requirement for booking here?
Minimum stay requirements depend on the property's policies. Review the specific rental's rules or contact the owner directly if you have questions about stay duration.
Round Top Top Rated Vacation Rentals
AU $260/Night
7 Nights - AU $1,822
