Why Choose Rent By Owner for your Old Bend Ski Chalets?
What makes our Ski Chalets special?
Popular Areas for Old Bend Ski Chalets
Where are the best neighborhoods to stay in Old Bend?
In Old Bend, you can enjoy a charming neighborhood that offers convenient access to outdoor activities and cozy accommodations perfect for your stay. Staying in this area places you close to the natural beauty and recreational opportunities that make Bend a sought-after destination for outdoor enthusiasts. Whether you're seeking tranquility or adventure, booking your ski chalets here ensures a comfortable and memorable experience in Oregon's premier mountain town.
Orchard District
Situated close to the heart of the region, this neighborhood offers convenient access to outdoor activities and scenic views, making it an ideal choice for those seeking a peaceful retreat with easy proximity to ski chalets.
View 81+ Rentals in Orchard DistrictSouthern Crossing
Known for its quiet streets and friendly atmosphere, Southern Crossing provides a perfect setting for exploring the area's natural beauty while enjoying comfortable stays in nearby ski accommodations designed for relaxing mountain getaways.
View 111+ Rentals in Southern CrossingLarkspur
This charming neighborhood blends convenience with tranquility, offering easy access to the region's outdoor adventures and a selection of inviting ski chalets that cater to visitors seeking both adventure and comfort.
View 69+ Rentals in LarkspurBest Times to Visit Old Bend
When should you plan your Ski Chalets stay?
To make the most of your stay in this destination, consider visiting during the winter months when snow transforms the landscape into a perfect setting for enjoying cozy ski chalets and outdoor activities, ensuring you experience the region at its most scenic and vibrant.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination becomes a popular spot for skiing enthusiasts seeking reliable and well-located ski chalets in the area. Expect ideal snow conditions and vibrant après-ski activities.
Spring Break (March to April)
Spring marks the peak season for those looking to enjoy late-season snow sport adventures in this region. The ski chalets here are perfect for travelers wanting to experience quality snow and longer daylight hours.
Off-Season Highlights
Late Spring (May to June)
As the region transitions into warmer weather, demand for ski chalets declines, making it an excellent time for quieter stays and exploring outdoor scenery without the crowds.
Fall (September to November)
Before the winter rush begins, this is a peaceful period when you can find good deals on accommodations and enjoy the area's scenic beauty and crisp air.
Weekly Weather Forecast for Old Bend
How to Book Your Old Bend Ski Chalets
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Old Bend
Common Ski Chalets 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
- Private outdoor decks or patios to enjoy the fresh mountain air.
- Accessible fire pits for cozy evenings after a day on the slopes.
- Well-maintained hot tubs with scenic views of the surrounding landscape.
- Comfortable outdoor lounging furniture perfect for relaxing after outdoor adventures.
- Driveways or parking areas designed for ease of access during winter months.
- Secure storage spaces for ski equipment and outdoor gear.
- Beautiful landscaped yards that enhance your outdoor experience in this destination.
Top Attractions Around Old Bend
What attractions are nearby?
While staying in this charming area, you can enjoy a variety of outdoor activities such as snowboarding, cross-country skiing, and snowshoeing at nearby winter sports facilities, or explore scenic hiking trails and mountain biking routes during the warmer months, offering year-round adventure opportunities just moments from your cozy ski chalet.
Family Activities
- Deschutes River Trail Embark on a family-friendly hike or paddle along the scenic Deschutes River, offering beautiful views and outdoor fun for all ages.
- High Desert Museum Discover engaging exhibits and live demonstrations that showcase the area’s rich wildlife and cultural history, perfect for curious minds.
- Bend Factory Stores Enjoy a relaxed shopping experience at this outlet mall, ideal for families seeking great deals and local finds in the region.
- Pine Nursery Park Spend quality time outdoors at this expansive park featuring playgrounds, walking paths, and picnic areas amidst natural beauty.
Adult Activities
- Guided Mountain Biking Tours: Experience the thrill of exploring the scenic trails in this area on a guided mountain biking tour designed for adults seeking adventure and breathtaking views.
- Indulge in local wine tasting events that highlight regional vineyards, offering a relaxing way to enjoy the area's vibrant culinary scene.
- Spa and Wellness Centers: Unwind at luxurious spas that provide rejuvenating treatments, perfect for a peaceful retreat after outdoor activities in this destination.
- Craft Beer Sampling: Discover the region’s craft beer culture by visiting local breweries known for their innovative brews and welcoming atmospheres.
Other Places to Stay in Old Bend, OR
Old Bend Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead and Book Early: Secure your preferred ski chalets in the area well in advance to ensure availability during peak seasons and special events.
- Explore Local Winter Activities: Take advantage of nearby outdoor pursuits such as snowboarding, cross-country skiing, or scenic winter walks to make your stay more memorable.
- Enjoy Scenic Drives and Views: Discover the breathtaking landscapes surrounding here by exploring the region’s scenic routes, especially during sunrise or sunset for optimal photo opportunities.
- Utilize Local Resources: Connect with local visitor centers or rental providers for insider tips on the best local dining, shopping, and hidden gems in this destination.
Transportation Options
- Personal Vehicles: Renting a car provides the flexibility to explore the scenic region and access your preferred ski chalets with ease.
- Shuttle Services: Local shuttle options connect visitors from nearby airports and key points throughout the area, making transportation convenient without the need for a personal vehicle.
- Public Transit: The regional bus systems offer affordable and reliable transportation between popular destinations and accommodations here.
- Taxis and Rideshare Services: Taxis and apps like Uber or Lyft provide on-demand transportation for quick trips within the neighborhood or to nearby ski resorts.
Local Customs Options
- Native American Heritage Understanding and respecting the area's rich Native American history is essential when visiting here, where local tribes have long traditions rooted in the land.
- Community Events Participating in seasonal festivals and gatherings is a common way to embrace the region’s friendly spirit and celebrate local customs.
- Outdoor Etiquette When exploring the natural landscapes surrounding here, it’s important to follow practices that preserve the environment, such as Leave No Trace principles.
- Local Art and Craftsmanship Appreciating the area’s unique art scene and handcrafted goods offers a window into its cultural identity and artistic heritage.
Frequently Asked Questions About Old Bend Rental Ski Chalets
1. What are the top Ski Chalets in Old Bend?
There are a lot of options in Old Bend. If you plan on staying in the Old Bend area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Old Bend:
- Bernhard Justice- Salt Hot Tub, 100+ Wifi, Gas Firepl, EV plug, Walkable!
- Green Gables-2 Fireplaces,Salt Hot tub, 100+mbps Wifi, AC, Bikes, Big Yard,Walk!
- Bluebird Day - Crater Retreat
- Located on Bend's most sought after historic district street, provides the perfe
- Fir Millhouse - Lovely historic cottage in downtown Bend
- Historic Drake Cottage 30 Day Rental. Across from Drake Park, Mirror Pond, downtown Bend. Furnished.
- North Sister - Bungalow Charm, Fireplace, Queen bed, Parking
- Adorable 3 bedroom 1/2 mile to Downtown & Old Mill
- The Hastings House - Walker's Paradise W/Hot Tub
- Sweet Spot- Oasis in Walkable Old Bend, Salt Hot Tub, AC, 100+mbps Wifi, 30 nts
2. How many Ski Chalets are available in Old Bend?
Currently, the total number of properties listed by RBO in 2026 is over 140 in the Old Bend area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Old Bend.


























