Discover Your Ideal Hillside, Colorado Vacation Rentals for a Memorable Getaway
Discover Your Perfect Hillside Vacation Homes
Best Vacation Homes in Hillside
- Pet Friendly
- Balcony/Terrace
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- Wheelchair Accessible
- Parking
- Pet Friendly
- Balcony/Terrace
- Pet Friendly
- Security/Safety
- Child Friendly
Hillside Luxury Rentals
- Parking
- Pool
- TV
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- TV
- Parking
- Pet Friendly
- TV
- Parking
- TV
- Balcony/Terrace
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- TV
- Balcony/Terrace
Hillside Pet Friendly Vacation Rentals
- Pet Friendly
- Security/Safety
- Child Friendly
- Parking
- Pet Friendly
- Accessibility
- Air Conditioner
- Parking
- Pet Friendly
- Pet Friendly
- Security/Safety
- Bedding/Linens
- Parking
- Pet Friendly
- Accessibility
- Parking
- Pet Friendly
- TV
- Parking
- Pet Friendly
- TV
- Air Conditioner
- Parking
- Pet Friendly
Hillside Large Vacation Homes
- Parking
- TV
- Security/Safety
- Air Conditioner
- Parking
- View
- Parking
- Pet Friendly
- TV
- Air Conditioner
- TV
- Balcony/Terrace
- Child Friendly
Why Choose Rent By Owner for your Hillside Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Hillside
When should you plan your Vacation Rentals stay?
Choosing the ideal time to vacation here ensures you experience the region's natural beauty and outdoor activities at their best, making your stay in Hillside, Colorado, USA, truly memorable.
Peak Season Highlights
Summer (June to August)
During the warmest months, you can enjoy the region's outdoor activities and scenic views at their best, making it a popular time for visitors seeking outdoor adventures.
Winter (December to February)
This is when the area transforms into a winter wonderland, attracting travelers looking for snow sports and cozy getaways amidst picturesque snowy landscapes.
Off-Season Highlights
Spring (March to May)
Late spring offers a quieter atmosphere as the region begins to bloom, ideal for those seeking more peaceful surroundings with fewer tourists.
Fall (September to November)
Autumn showcases vibrant foliage and cooler weather, providing a serene ambiance perfect for exploring the area's natural beauty without the crowds.
Weekly Weather Forecast for Hillside
How to Book Your Hillside Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Hillside
Common Vacation Rentals Amenities
What amenities can you expect?
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 spacious outdoor seating areas, perfect for relaxing and taking in the scenic views of the surrounding mountains.
- Take advantage of private patios or decks to dine al fresco amidst fresh mountain air.
- Make use of outdoor grills or barbecues to host cookouts while enjoying the natural beauty of the region.
- Experience the convenience of dedicated outdoor parking spaces, ensuring easy access during your stay.
- Benefit from landscaped gardens or yards that provide a peaceful environment for outdoor activities.
- Utilize nearby hiking trails or nature walk access points directly from your rental property.
- Some properties feature fire pits or outdoor fireplaces for cozy evenings under the stars.
Top Attractions Around Hillside
What attractions are nearby?
Here, you can explore outdoor activities such as hiking, biking, and scenic nature walks that showcase the stunning landscapes of this destination’s surrounding region.

Family Activities
- Hiking Trails Exploration: Discover scenic trails perfect for family hikes that showcase the natural beauty of this Colorado region.
- Wildlife Viewing Tours: Enjoy guided tours where you can observe local wildlife in their native habitat, offering educational fun for all ages.
- Local Museum Visits: Engage with interactive exhibits and learn about the area's history and culture at nearby museums suited for family outings.
- Picnic in Scenic Parks: Relax and unwind with a family picnic in lush parks that provide playgrounds and open spaces to enjoy here.
Adult Activities
- Hiking in the nearby Colorado Rockies: You can explore scenic trails that offer breathtaking views and a chance to experience the region's rugged natural beauty.
- Visiting local art galleries and studios: Discover the vibrant arts scene here by browsing unique exhibitions that showcase regional talent and creativity.
- Enjoying outdoor dining experiences: Relish delicious cuisine at charming cafes and restaurants that provide a cozy atmosphere with beautiful surroundings.
- Relaxing at local wellness spas: Indulge in rejuvenating treatments and massages designed to help you unwind amidst the tranquil setting of this destination.
Hillside Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Seasonal Activities: Take advantage of the area's distinct seasons by booking outdoor adventures or local events in advance to enhance your stay.
- Explore Local Cuisine and Markets: Discover the region's culinary offerings and fresh produce by visiting nearby markets and dining establishments during your visit.
- Utilize Nearby Nature Trails: Maximize your outdoor experience by exploring the scenic trails and parks that showcase the natural beauty of this destination.
- Communicate with Hosts for Insider Tips: Reach out to your vacation rental hosts to receive personalized recommendations and hidden gems around here that can enrich your trip.
Transportation Options
- Personal Vehicle: Having your own car offers the most flexibility to explore this scenic region at your own pace and easily access all local attractions.
- Public Transit: The area's bus services provide an affordable and convenient way to travel between popular destinations in the region without the hassle of parking.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber or Lyft are readily available for quick, direct transportation throughout here and nearby neighborhoods.
- Bicycle Rentals: Exploring via bicycle provides a sustainable and healthy way to enjoy the natural beauty of this destination while getting some exercise.
Local Customs Options
- Local Mountain Traditions: You will notice a deep respect for the natural environment, especially surrounding mountain customs that emphasize outdoor activities and conservation efforts.
- Western Heritage Celebrations: Participating in regional festivals often involves traditional Western attire and festivities that honor the area's historic ranching roots.
- Indigenous Cultural Acknowledgments: Respect for Native American history is woven into community events, highlighting the region's rich indigenous heritage.
- Community Sharing of Local Cuisine: When dining out or preparing meals, expect a focus on locally sourced ingredients and traditional regional dishes that reflect this area's culinary customs.
Frequently Asked Questions About Hillside?
1. What are the top vacation rentals in Hillside?
There are a lot of options in Hillside. If you plan on staying in the Hillside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hillside:
- Modern Log Cabin in Colorado Wilderness
- A Little Piece Of Colorado Heaven
- Magical Cabin below the Sangre de Cristos
- Spacious Westcliffe Home: Hot Tub, StarLink, Views!
- Ravens Fun Bunkhouse with Fire Pit/Grill & Patio
- The "Quintessential" Cabin in the Woods.
- Ravens' Aspen Breeze 3rm Suite w/Fire Pit & Grill
- Spacious Home-Mountain & Valley Views - Dark Sky
- 4-Season Mountain Escape with Breathtaking View!
- Hunter's Special: Lodge with Six Bedrooms + Loft. ATV Access to Rainbow Trail.
2. Which vacation homes in Hillside are best for families?
If you are looking for a family-friendly vacation home in Hillside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hillside:
3. How many Rentbyowner vacation rentals are available in Hillside?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 95 in the Hillside 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 Hillside.