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Best Vacation Homes in First On The Hill

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First On The Hill Pet Friendly Vacation Rentals

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9.8 (269 Reviews)
Apartment
Wall Street Suites
  • Air Conditioner
  • Parking
  • Pet Friendly
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10.0 (1 Review)
House
Huckleberry Cottage
  • Parking
  • Pet Friendly
  • Security/Safety
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First On The Hill Large Vacation Homes

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Why Choose Rent By Owner for your First On The Hill Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for First On The Hill Vacation Rentals

Where are the best neighborhoods to stay in First On The Hill?

When choosing where to stay in Bend, Oregon, First On The Hill offers a charming neighborhood experience that combines convenience with scenic beauty. This area provides easy access to the natural surroundings and local amenities, making it an ideal location for exploring all that Bend has to offer. As you search for vacation rentals, you'll find that staying in First On The Hill allows you to enjoy a peaceful atmosphere while remaining close to the vibrant outdoor activities and cultural attractions of the city. Booking your accommodation here ensures a comfortable and reliable base for your Bend adventure.

Boyd Acres

Located within easy reach of the region's outdoor activities, Boyd Acres offers a convenient base for exploring Bend and its surrounding natural beauty. Staying here provides quick access to local amenities and a comfortable retreat after days spent enjoying the area's scenic landscapes.

View 38+ Rentals in Boyd Acres

Best Times to Visit First On The Hill

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you make the most of your experience in this region, where seasonal weather patterns and local events can significantly enhance your stay in First On The Hill, Bend, Oregon.

Peak Season Highlights

summer
Summer (June to August)

This is the most popular time to visit the area, as the warm weather and long days attract outdoor enthusiasts and adventure seekers. Expect higher demand for vacation rentals during this peak season.

Average Temperature Daytime: 75-85°F - Nighttime: 45-55°F
autumn
Fall (September to November)

The region offers stunning autumn foliage and crisp air, making it an ideal time for scenic exploration. Vacation rental prices tend to be at their highest during these months due to increased visitor interest.

Average Temperature Daytime: 60-70°F - Nighttime: 35-45°F

Off-Season Highlights

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Winter (December to February)

During winter, fewer visitors come to enjoy the calm and quieter atmosphere of here, often resulting in lower rental rates. Ideal for those seeking a peaceful retreat in a snowy landscape.

Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F
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Spring (March to May)

As the region awakens from winter, spring offers fewer crowds and more affordable vacation rentals. The season provides a refreshing start with blooming scenery and mild temperatures.

Average Temperature Daytime: 50-65°F - Nighttime: 30-40°F

Weekly Weather Forecast for First On The Hill

How to Book Your First On The Hill 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 First On The Hill

More Top-Rated Vacation Rentals in First On The Hill Area

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 a private outdoor patio or deck perfect for relaxing and soaking up the sunshine.
  • Take advantage of a spacious yard ideal for outdoor activities or family gatherings.
  • Make use of comfortable outdoor furniture to dine alfresco amid scenic views of the region.
  • Benefit from easy access to nearby hiking and biking trails that showcase the area's natural beauty.
  • Utilize amenities such as a barbecue grill for outdoor cooking experiences.
  • Relax by an outdoor fire pit under clear night skies, perfect for evenings in the region's crisp air.
  • Discover outdoor storage options for your gear and adventure equipment during your stay here.

Top Attractions Around First On The Hill

What attractions are nearby?

Explore the area's abundant outdoor activities and scenic attractions just moments from your accommodation, making it easy to enjoy everything that this vibrant destination has to offer.

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Family Activities

  • Deschutes River Recreation: Enjoy family-friendly activities like fishing, kayaking, and paddleboarding along this scenic river that flows through the area.
  • Pine Mountain Observatory: Take a daytime visit to explore the stars and planets with the family at this local observatory offering engaging educational programs.
  • Bend's Old Mill District: Discover a variety of shops, kid-friendly dining options, and outdoor spaces perfect for a leisurely family stroll.
  • The Highlands Neighborhood Park: Spend quality time outdoors at this nearby park featuring playgrounds, picnic areas, and open spaces ideal for family fun.
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Adult Activities

  • Bend Ale Trail Tours: Embark on a guided or self-guided experience along the area's renowned breweries, savoring craft beers while enjoying the scenic views of this vibrant destination.
  • Deschutes River Activities: Engage in kayaking, paddleboarding, or tubing on the river to enjoy the natural beauty and outdoor adventure opportunities that this region offers.
  • Downtown Bend Dining Experiences: Explore the local culinary scene by visiting a variety of restaurants and cafes that showcase the region's fresh, locally sourced ingredients.
  • Golf at Remarkable Courses: Play a round at championship golf courses nestled in the area, offering stunning mountain vistas and a relaxing environment for enthusiasts of all skill levels.

First On The Hill Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Outdoors: Take advantage of the abundant natural beauty surrounding the area by planning outdoor activities like hiking or biking to fully enjoy the scenic landscape.
  • Utilize Local Resources: Connect with community centers or visitor information centers to discover hidden gems and insider tips for a more authentic experience.
  • Plan Ahead: Book your preferred vacation rentals early, especially during peak seasons, to secure the best properties and uninterrupted access to this destination’s highlights.
  • Respect the Environment: Practice eco-friendly habits during your stay to help preserve the region’s pristine outdoors for future visitors to cherish.

Transportation Options

  • Local Bus Services: Convenient local transit options connect you to key points around the area, making it easy to explore without a car.
  • Bike Rentals: Embrace the region’s outdoor spirit by renting a bicycle for a flexible and eco-friendly way to navigate this destination's scenic streets.
  • Taxi and Rideshare Services: Reliable taxi and rideshare options are readily available for quick, door-to-door transportation throughout the neighborhood.
  • Private Car Rentals: Renting a car offers the flexibility to explore beyond the immediate vicinity at your own pace, perfect for discovering all that here has to offer.

Local Customs Options

  • Respect for Nature: Locals in this region deeply value outdoor preservation, so you'll find a strong emphasis on environmental respect when exploring here.
  • Community Gatherings: Participating in local events and festivals is a common way visitors engage with the area's friendly and welcoming community.
  • Hospitality Customs: Warm welcomes and courteous interactions are standard, reflecting the region’s tradition of friendly hospitality toward guests.
  • Outdoor Etiquette: When enjoying the scenic landscapes, it's customary to follow trail and park guidelines to help maintain the natural beauty here.

Frequently Asked Questions About First On The Hill?

1. What are the top vacation rentals in First On The Hill?

There are a lot of options in First On The Hill. If you plan on staying in the First On The Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in First On The Hill:

2. How many vacation rentals have private pools in First On The Hill?

There are 12 vacation rentals with private pools near First On The Hill. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in First On The Hill are best for families?

If you are looking for a family-friendly vacation home in First On The Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in First On The Hill:

4. How many Rentbyowner vacation rentals are available in First On The Hill?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 898 in the First On The Hill 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 First On The Hill. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the owner and specific listing. To understand the exact terms, please refer to the individual rental listing or contact the host directly before booking.

6. Are there any amenities or services included with my booking?

Amenities are detailed within each property listing. For information about additional services or special features, review the listing description or reach out to the host for clarification.

7. How do I secure my reservation and what are the payment options?

Reservations are secured through the booking platform, which accepts various payment methods. Specific details regarding deposits or full payments can be found in the booking confirmation or by contacting the property owner.

8. What is the check-in and check-out process for this destination?

Check-in and check-out procedures are outlined in the property listing. Contact the host ahead of your arrival to receive specific instructions or if you have any special requests.

9. Are there any restrictions or rules I should be aware of before booking?

Each property may have its own house rules or restrictions. Be sure to read the listing details carefully, and if you have questions, communicate directly with the host to ensure a smooth stay.

First On The Hill Top Rated Vacation Rentals

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