Discover Your Ideal Gateway Retreat with Top-Rated Vacation Rentals in Madras, Oregon
Discover Your Perfect Gateway Vacation Homes
Best Vacation Homes in Gateway
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Gateway Luxury Rentals
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Gateway Pet Friendly Vacation Rentals
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Gateway Large Vacation Homes
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Why Choose Rent By Owner for your Gateway Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Gateway
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can enhance your experience, as the region offers different attractions and weather conditions throughout the year, making it essential to consider seasonal factors when booking your vacation rentals here.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather, making it ideal for outdoor activities and exploring the scenic region. It's a lively time to enjoy your stay in this area with longer daylight hours.
Fall (September to November)
Early fall offers mild temperatures and stunning seasonal changes, attracting visitors who want to experience the vibrant fall foliage and pleasant weather in the region.
Off-Season Highlights
Winter (December to February)
The winter season sees cooler temperatures and quieter surroundings, making it a perfect time for travelers seeking peaceful getaways away from peak crowds.
Spring (March to May)
Spring brings gradually warming weather and blooming landscapes, offering a more tranquil experience as nature begins to awaken in this part of Oregon.
Weekly Weather Forecast for Gateway
How to Book Your Gateway Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Gateway
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
- Access to spacious outdoor decks or patios to enjoy the fresh air and scenic views.
- Private or shared barbecue grills ideal for outdoor cooking during your stay.
- A well-maintained backyard or garden space perfect for relaxing or outdoor activities.
- Outdoor fire pits or fire rings to gather around in the cooler evenings.
- Dedicated parking areas that make exploring the area convenient without worrying about urban parking restrictions.
- Proximity to hiking trails, biking paths, or other adventure opportunities in the surrounding region.
- Potential access to outdoor recreational amenities such as tennis courts, swimming pools, or playgrounds, depending on the property.
Top Attractions Around Gateway
What attractions are nearby?
In this area, you can enjoy a variety of outdoor activities such as exploring scenic trails, fishing, and boating at nearby lakes, providing the perfect backdrop for your adventurous and relaxing pursuits during your stay.

Family Activities
- Deschutes River Activities: Enjoy family-friendly water adventures such as fishing, kayaking, or paddleboarding along the scenic Deschutes River that runs through the area.
- La Pine State Park: Explore this nearby park with its easy walking trails, picnicking spots, and opportunities for wildlife watching suitable for visitors of all ages.
- Gateway City Daze Festival: Attend this local community event featuring live entertainment, arts and crafts, and family activities that celebrate the region’s vibrant culture.
- The High Desert Museum: Discover interactive exhibits and outdoor displays that showcase the region's natural history and indigenous culture, perfect for educational family outings.
Adult Activities
- Exploring the High Desert Museum: Discover engaging exhibits and native wildlife that highlight the unique landscape of the region.
- Enjoying Outdoor Recreation at Fish Lake: Engage in fishing, kayaking, or simply relaxing by the water at this popular local spot.
- Hiking in the Cascade Mountains: Experience scenic trails and panoramic views within the nearby mountain ranges, perfect for outdoor enthusiasts.
- Visiting Local Art Galleries and Craft Shops: Immerse yourself in the area's vibrant arts scene through unique galleries and craft stores showcasing regional talent.
Gateway Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the area's natural landscape by planning outdoor adventures like hiking or fishing, which showcase the region's scenic beauty and enhance your stay.
- Discover Nearby Attractions: Use your vacation rental as a base to visit nearby points of interest, ensuring you experience the best that Madras and its surroundings have to offer.
- Check Weather Conditions in Advance: Stay informed about the local climate to pack appropriately and make the most of your outdoor plans during your visit.
- Engage with the Local Community: Embrace the area's culture by participating in local events or visiting community spots, enriching your travel experience in this destination.
Transportation Options
- Madras Municipal Airport: This small regional airport provides convenient domestic flights, making it easy for you to reach the area quickly.
- Rental Car Services: Numerous car rental agencies operate here, giving you the flexibility to explore the region at your own pace from your vacation rental.
- Taxi and Ride-Sharing Services: Local taxis and ride-sharing options are readily available to get you around nearby attractions or to and from the airport efficiently.
- Public Transit: Bus services connect Gateway to surrounding towns and cities, offering an affordable transportation option during your stay.
Local Customs Options
- Western Oregon Hospitality: Locals take pride in welcoming visitors with friendly gestures that reflect the region’s warm and inclusive spirit.
- Native American Heritage: Respect for the area's indigenous cultures is demonstrated through community events and local storytelling traditions, offering insight into the region's rich history.
- Outdoor Community Values: Engaging in conservation efforts and outdoor activities like fishing and hiking showcases the area’s commitment to preserving its natural beauty.
- Local Craftsmanship: Supporting artisans and craft vendors highlights the region’s appreciation for handmade goods and traditional skills within the community.
Frequently Asked Questions About Gateway?
1. What are the top vacation rentals in Gateway?
There are a lot of options in Gateway. If you plan on staying in the Gateway area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Gateway:
- Stunning Hillside Retreat w/ Panoramic Views, Pet Friendly, Pool Table, Huge Deck, 1 Mile 2 Downtown
- Madras Oak House ● Entire Home w/Unopposed Mountain View ● Fireplace ● BBQ
- Madras Oak House
- Lake Simtustus Resort Juniper Hill Tiny Home #11 - Hot Tub
- NEW! Eagles Landing B04 Tiny Home - Hot Tub
- Lake Simtustus Resort Juniper Hill Tiny Home #10 - Hot Tub
- Lake Simtustus Resort Crown Point Tiny Home #12 - Hot Tub
- The Bunk House at Cross Keys
- Bunk House
- The Inn at Cross Keys Station
2. Which vacation homes in Gateway are best for families?
If you are looking for a family-friendly vacation home in Gateway, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Gateway:
3. How many Rentbyowner vacation rentals are available in Gateway?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 37 in the Gateway 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 Gateway.
4. What is the cancellation policy for vacation rentals in Gateway, Madras, Oregon?
5. How do I confirm my reservation and what payment methods are accepted?
6. Are there any house rules I should be aware of before booking?
7. What amenities are generally available in vacation rentals here?
8. Is there a minimum stay requirement for bookings in this region?
Gateway Top Rated Vacation Rentals
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