Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Ashland, Oregon
Ashland, Oregon, offers a diverse range of Airbnb accommodations that cater to various preferences and budgets. Visitors can choose from charming cottages and rustic cabins nestled in the scenic surroundings, perfect for those seeking a tranquil retreat. For a more urban experience, there are modern apartments and stylish lofts located near downtown, providing easy access to Ashland's vibrant arts scene, including the renowned Oregon Shakespeare Festival. Additionally, guests can find unique stays such as eco-friendly homes and historic houses that reflect the town's rich heritage. Whether travelers are looking for a cozy room in a shared home or an entire property for a family getaway, Ashland's Airbnb options provide a comfortable and personalized lodging experience.
In Ashland, Oregon, short-term rentals, including those listed on platforms like Airbnb, are subject to specific regulations. Property owners must obtain a Conditional Use Permit to operate a short-term rental, which is only allowed in certain zones, primarily in the city's historic district. The property must be the owner's primary residence, and the rental is limited to a maximum of two bedrooms. Additionally, the city imposes a Transient Occupancy Tax (TOT) on short-term rentals, which is currently set at 10% of the rental income. This tax is collected by the property owner and remitted to the city. Compliance with these regulations is essential to legally operate a short-term rental in Ashland.
Managing an Airbnb in Ashland, Oregon, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to meet guest expectations, which includes regular cleaning, restocking essentials, and addressing any maintenance issues promptly. Given Ashland's popularity due to attractions like the Oregon Shakespeare Festival, effective marketing and competitive pricing strategies are crucial to attract guests year-round. Communication with guests is vital, from providing clear check-in instructions to being responsive to inquiries and feedback. Additionally, understanding and complying with local regulations and taxes related to short-term rentals is essential to avoid legal issues. Lastly, leveraging guest reviews to improve the property and service can enhance the overall guest experience and boost occupancy rates.
Ashland, Oregon, is renowned for its vibrant arts scene and natural beauty, making it a popular destination for visitors. The best areas to stay in an Airbnb include the downtown area, which offers easy access to the Oregon Shakespeare Festival, boutique shops, and a variety of dining options. Staying near Lithia Park is also ideal, as it provides a serene environment with beautiful trails and gardens, perfect for nature lovers. The Railroad District is another great option, known for its historic charm and proximity to local breweries and cafes. Each of these areas offers a unique experience, ensuring a memorable stay in Ashland.
Ashland, Oregon, is a promising market for Airbnb investments, primarily due to its vibrant cultural scene and natural beauty. Known for the Oregon Shakespeare Festival, Ashland attracts a steady stream of tourists and theater enthusiasts, ensuring a consistent demand for short-term rentals. The city's picturesque setting, nestled in the foothills of the Siskiyou and Cascade Ranges, also draws outdoor enthusiasts year-round, further boosting occupancy rates. Additionally, Ashland's charming downtown, with its boutique shops, art galleries, and farm-to-table dining, enhances its appeal as a travel destination. Investors can capitalize on these attractions by offering unique and comfortable accommodations that cater to both cultural tourists and nature lovers, making Ashland a lucrative market for Airbnb ventures.
As of the latest data, Ashland, Oregon, has seen a steady performance in its Airbnb market, with average monthly revenues for hosts typically ranging between $2,000 and $3,500. This range can vary significantly depending on factors such as location, property size, amenities offered, and seasonal demand, particularly given Ashland's popularity as a cultural and outdoor destination. The city's vibrant arts scene, highlighted by the renowned Oregon Shakespeare Festival, along with its proximity to natural attractions, contributes to a consistent flow of visitors, thereby supporting a healthy short-term rental market. Hosts who strategically price their listings and maintain high standards of hospitality often see higher occupancy rates and, consequently, increased revenue.
Ashland, Oregon, known for its vibrant arts scene and the renowned Oregon Shakespeare Festival, experiences a notable fluctuation in Airbnb occupancy rates due to its seasonal attractions. The peak season typically spans from late spring through early fall, coinciding with the festival's schedule, which draws a significant influx of visitors and results in higher occupancy rates during these months. Conversely, the winter months see a decline in tourist activity, leading to lower occupancy rates. However, Ashland's proximity to outdoor recreational areas, such as the nearby ski resorts and hiking trails, helps maintain a moderate level of interest throughout the year. Overall, the Airbnb market in Ashland is characterized by its strong seasonal demand, with occupancy rates peaking during the festival season and tapering off in the quieter winter months.
Why Choose Checkmate Rentals?
Other Property Managers | ||
---|---|---|
Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
What you get with Checkmate Rentals
Attract Guests

Listing on all top booking sites
Targeted digital marketing
High-definition photography
Custom copywriting
Manage Details

Dynamic rate-setting technology
Dedicated reservation agents
24/7 guest service
Consistent, professional cleaning
Stocking guest amenities
Payment processing
Take Care of You

Unlimited owner holds
No fixed contracts
Local staff in every market
Inspections and regular maintenance
Guest screening
Optional short-term rental insurance
Get in touch with us.
Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.
Direct Bookings
Earn more year after year as guests book their stay directly on our website.
Housekeeping
Make the perfect first impression with wall-to-wall cleanings before guests arrive.
Inspections
Know your property is guest-ready is top-to-bottom inspections after every booking.
Guest Damage Coverage
Save more when you let us cover accidental guest damage coverage up to $3k.
Smart Home Management
We manage your digital locks & noise monitoring tech in your home.
Fast Listings
Get your home fully listed and ready for guests in as little as 3 days.
Automated Touchpoints
Give guests a seamless experience with automated touchpoints from booking to checkout.
Owner Portal
Stay in the loop on your property with our easy-to-use owner portal that lets you check everything you need.
