Best Vacation Homes in South Side
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South Side Luxury Rentals
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South Side Pet Friendly Vacation Rentals
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South Side Large Vacation Homes
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Why Choose Rent By Owner for your South Side Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for South Side Vacation Rentals
Where are the best neighborhoods to stay in South Side?
Discover the vibrant neighborhoods of South Side in Billings, Montana, where your choice of accommodation can enhance your entire stay. This area offers a convenient location with easy access to local amenities and scenic views, making it an ideal place for travelers seeking comfort and convenience. Whether you're exploring the city’s cultural scene or simply relaxing in a cozy setting, choosing a carefully selected property in South Side ensures a seamless and enjoyable experience during your visit to Billings. With its welcoming atmosphere and prime location, South Side provides a perfect base for your Montana adventures.
North Park
Situated in the northern part of the region, North Park offers a peaceful setting where you can enjoy a quiet retreat while remaining close to key amenities. This area provides convenient access to local attractions and is ideal for travelers seeking a comfortable and accessible stay.
View 255+ Rentals in North ParkCentral - Terry
Located centrally within the city, Central - Terry is perfect for exploring the area's vibrant neighborhoods and cultural spots. Here, you’ll find a mix of amenities and easy connectivity, making it a smart choice for those wanting to experience the local vibe during their visit.
View 60+ Rentals in Central - TerryBest Times to Visit South Side
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you experience the region’s unique charm at its best, whether you're seeking outdoor adventures or relaxing stays in comfortable vacation rentals.
Peak Season Highlights
Summer (June to August)
During summer months, the area experiences warm weather perfect for exploring the region and enjoying outdoor activities. This is when demand for vacation rentals peaks, so early booking is recommended.
Fall (September to November)
Autumn offers mild temperatures and vibrant fall foliage, attracting visitors seeking scenic views and outdoor adventures. Vacation rentals tend to fill quickly during this colorful season.
Off-Season Highlights
Winter (December to February)
The quiet winter months bring cooler temperatures and fewer crowds, making it an ideal time to find more affordable vacation rental options and enjoy a peaceful stay here.
Spring (March to May)
As the region transitions into warmer weather, spring offers mild conditions and fewer travelers, providing a great opportunity to explore the area with less competition for rental properties.
Weekly Weather Forecast for South Side
How to Book Your South Side Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in South Side
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 outdoor grilling with private BBQ facilities available on the property.
- Relax in a spacious backyard or garden area perfect for outdoor gatherings and activities.
- Benefit from access to nearby parks or green spaces ideal for walking, jogging, or picnics.
- Make use of outdoor seating areas to unwind and soak up the local scenery.
- Take advantage of a patio or deck for outdoor dining during pleasant evenings.
- Utilize convenient off-street parking options for exploring the surrounding region effortlessly.
- Experience scenic views from the property’s outdoor vantage points, suitable for photography or quiet reflection.
Top Attractions Around South Side
What attractions are nearby?
In this vibrant area, you can enjoy nearby hiking trails, explore local parks, or indulge in recreational activities that showcase the natural beauty of Montana.
Family Activities
- ZooMontana: Spend a fun-filled day exploring this family-friendly zoo, home to native Montana animals and engaging exhibits that bring the region’s wildlife to life.
- Pictograph Cave State Park: Discover ancient rock paintings and enjoy easy hiking trails in this historic site that offers educational opportunities for all ages.
- Billings Depot: Experience the charm of this historic train depot with its seasonal events, art displays, and scenic surroundings perfect for family outings.
- The Rimrocks: Take in breathtaking views of the area from the iconic sandstone formations while enjoying outdoor activities suitable for every member of your family.
Adult Activities
- Billings Brewery Tours: Discover locally brewed beers on guided tours that highlight the region’s vibrant craft beer scene right here in the South Side area.
- Riverfront Park Activities: Enjoy a variety of outdoor pursuits along the scenic riverfront, including walking, biking, and relaxing by the water in this central part of the city.
- Local Art Galleries: Immerse yourself in regional culture by visiting galleries showcasing Montana artists, perfect for those seeking creative inspiration during your stay.
- Downtown Dining Experiences: Savor diverse culinary options at popular restaurants within the district, offering authentic flavors unique to this destination.
Other Places to Stay in South Side, MT
South Side Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Sample the regional cuisine by visiting nearby restaurants to enhance your stay in South Side, Billings, Montana.
- Plan outdoor activities: Take advantage of the area's beautiful natural surroundings with outdoor adventures that showcase Montana's scenic landscape.
- Utilize local transportation: Use public transit or rental options to easily navigate here and access all the destinations in the region without hassle.
- Discover hidden gems: Seek out lesser-known spots around South Side to get a more authentic experience and make your trip truly memorable.
Transportation Options
- Billings Transit System: Local buses provide reliable transportation around the area, making it easy to explore without a car.
- Rental Cars: Several rental agencies near your vacation rental in South Side, Billings, offer convenient options for exploring the region at your own pace.
- Taxi and Rideshare Services: Taxis and rideshare companies like Uber and Lyft operate here, ensuring quick and hassle-free travel within the region.
- Bicycle Rentals: Cycling is a popular way to enjoy this destination, with bike rentals available to help you traverse the local streets and scenic areas comfortably.
Local Customs Options
- Respect for Local Art and Heritage: You will find that embracing the area's artistic expressions honors the local culture in South Side, Billings, Montana.
- Community Events Participation: Engaging in neighborhood gatherings and festivals offers a genuine experience of the region's traditions here.
- Outdoor Etiquette: Observing proper outdoor manners, especially during recreational activities, helps maintain harmony in this part of Montana.
- Respect for Personal Space: Being considerate of neighbors and respecting private property reflects the courteous spirit prevalent throughout the area.
Frequently Asked Questions About South Side?
1. What are the top vacation rentals in South Side?
There are a lot of options in South Side. If you plan on staying in the South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Side:
- Renovated home in vintage neighborhood, close to airport, hospitals, & downtown.
- Luxury living, or a business sutie, 5 minutes MSU-B, and the Medical Corridor.
- Centrally located for event attending, shopping & visiting family!
- Rooftop Patio Downtown
- Tranquil 5 bedroom home with large deck and yard
- Pets & Kids Love this Montana Dream Home!
- Quaint sunny cottage that rests in the historical neighborhood of Billings
- Bo's Old West Landing w/Hot Tub and Sunrise Views
- Historic Home in Prime Location!
- Big Sky Retreat
2. How many vacation rentals have private pools in South Side?
There are 6 vacation rentals with private pools near South Side. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in South Side are best for families?
If you are looking for a family-friendly vacation home in South Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Side:
4. How many Rentbyowner vacation rentals are available in South Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 370 in the South Side 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 South Side.
