Discover Your Perfect Ashland Vacation Homes

Ashland Luxury Rentals

See More Ashland Luxury Vacation Rentals
Find More Ashland Villas, Resorts, & Rentals on BedroomVillas

Ashland Pet Friendly Vacation Rentals

|
10.0 (2 Reviews)
Apartment
The Barn at Emigrant Creek
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
|
9.8 (40 Reviews)
Apartment
A Cowslip's Belle Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
10.0 (57 Reviews)
Cabin
Hyatt Prairie Mountain Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Ashland on PetFriendly.io

Why Choose Rent By Owner for your Ashland Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Popular Areas for Ashland Vacation Rentals

Where are the best neighborhoods to stay in Ashland?

When choosing where to stay in Ashland, Oregon, selecting the right neighborhood can greatly enhance your visit. Whether you're seeking a peaceful retreat close to nature or a vibrant area near the town’s cultural highlights, Ashland offers diverse neighborhoods to suit your preferences. Each neighborhood provides easy access to local attractions, charming cafes, and scenic parks, making it simple to explore and enjoy everything this unique city has to offer. By booking your vacation rentals in the most suitable neighborhood for your interests, you ensure a memorable and comfortable stay in Ashland, Oregon.

Historic Downtown District

Staying in this vibrant area places you at the heart of Ashland’s cultural scene, where charming streets and local shops create an inviting atmosphere. It's the perfect base for exploring the region's artistic events and downtown amenities.

View 305+ Rentals in Historic Downtown District

Historic Railroad District

Opting for a stay here offers easy access to the area's rich transportation history while providing convenient proximity to natural parks and outdoor activities. This neighborhood serves as a hub for those wanting to explore both nature and history.

View 57+ Rentals in Historic Railroad District

Siskiyou-Hargadine Historic District

Residing in this historic district immerses you in Ashland’s architectural legacy, with beautifully preserved buildings that add charm to your stay. It’s ideal for visitors seeking a blend of history and community ambiance.

View 32+ Rentals in Siskiyou-Hargadine Historic District

Skidmore Academy Historic District

Choosing accommodations here connects you to Ashland’s educational and historic roots, offering a peaceful setting close to local landmarks. It’s suited for travelers who value a quiet environment rich in history.

View 272+ Rentals in Skidmore Academy Historic District

Best Times to Visit Ashland

When should you plan your Vacation Rentals stay?

Discovering the optimal time to visit here ensures you enjoy the region's unique charm and vibrant events, making your stay in Ashland an unforgettable experience with the perfect vacation rentals tailored to your travel preferences.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, the area experiences warm weather and longer days, making it ideal for outdoor activities and exploration.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 50°F to 60°F
autumn
Fall (September to November)

Autumn offers vibrant foliage and a lively cultural scene, attracting visitors who want to enjoy the region's scenic beauty and local festivals.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 40°F to 50°F

Off-Season Highlights

image
Winter (December to February)

In winter, cooler temperatures and fewer crowds create a cozy atmosphere, perfect for relaxed stays and enjoying the serene landscape.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
image
Early Spring (March to April)

As the region transitions from winter, quieter periods with mild weather offer a peaceful setting for those seeking less crowded accommodations.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Ashland

How to Book Your Ashland 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 Ashland

More Top-Rated Vacation Rentals in Ashland 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 spacious outdoor patio or deck for relaxing and entertaining amid the scenic surroundings.
  • Take advantage of private gardens or landscaped yards that showcase the natural beauty of the area.
  • Make the most of outdoor dining areas perfect for savoring meals al fresco while soaking up the fresh air.
  • Benefit from outdoor fire pits or fireplaces, ideal for cozy evenings under the stars.
  • Relax in a hot tub or spa with views of the picturesque landscape.
  • Discover access to scenic hiking trails or nature walks directly from your rental property.
  • Utilize covered outdoor spaces such as porches or verandas to enjoy the mild here climate year-round.

Top Attractions Around Ashland

What attractions are nearby?

While staying in your vacation rental here, you can enjoy a variety of outdoor activities and cultural experiences nearby, making this destination an ideal base for exploring the vibrant arts scene and scenic natural landscapes of the region.

image
image

Family Activities

  • Oregon Shakespeare Festival: Enjoy family-friendly performances at this renowned festival, offering engaging theater experiences for all ages in the heart of the region.
  • ScienceWorks Hands-On Museum: Discover interactive exhibits that captivate children and adults alike, making learning about science both fun and educational here in the area.
  • Ashland Canal Trail: Take a leisurely family walk or bike ride along this scenic trail, perfect for exploring the natural beauty surrounding the city.
  • Fun with Nature at Lithia Park: Spend a relaxing day outdoors in this picturesque park featuring playgrounds, picnic areas, and beautiful scenery for family adventures in the region.
image

Adult Activities

  • Shakespeare Festival: Experience world-class theatrical performances that celebrate the region's rich cultural heritage and artistic talent during the renowned summer festival.
  • Mississippi River Trail Hiking: Explore scenic trails along the nearby river, offering breathtaking views and a peaceful retreat in the midst of nature’s beauty.
  • Wine Tasting Tours: Sample local wines at acclaimed vineyards and wineries nestled within this destination’s picturesque landscape, perfect for wine enthusiasts seeking a relaxed outing.
  • Downtown Arts Walks: Discover vibrant galleries, boutique shops, and live performances as you stroll through the charming core of the area’s arts scene.

Other Places to Stay in Ashland, OR

Tashi Choling Buddhist Center
Tashi Choling Buddhist Center Vacation Rentals
Ariel Ski Lift
Ariel Ski Lift Vacation Rentals
Windsor Ski Lift
Windsor Ski Lift Vacation Rentals
Comer Ski Lift
Comer Ski Lift Vacation Rentals
Mount Ashland Ski Area
Mount Ashland Ski Area Vacation Rentals
Historic Downtown District
Historic Downtown District Vacation Rentals
Ashland Library
Ashland Library Vacation Rentals
North Mountain Park
North Mountain Park Vacation Rentals
Angus Bowmer Theatre
Angus Bowmer Theatre Vacation Rentals
Skidmore Academy Historic District
Skidmore Academy Historic District Vacation Rentals
Historic Railroad District
Historic Railroad District Vacation Rentals
Siskiyou-Hargadine Historic District
Siskiyou-Hargadine Historic District Vacation Rentals
More Places to Stay Near Ashland

Ashland Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar to align your stay with popular festivals and performances that showcase the region's vibrant arts scene.
  • Explore the Neighborhoods: Take time to discover different neighborhoods and their unique charms, ensuring you experience the full diversity of this destination.
  • Utilize Local Resources: Visit nearby visitor centers or online guides to find hidden gems and authentic experiences exclusive to this region.
  • Book Your Stay Strategically: Choose vacation rentals close to major attractions and public transportation to maximize your convenience and immersion during your visit here.

Transportation Options

  • Ashland Transit Services: This local bus system offers convenient and affordable transportation options within the area, making it easy for you to explore without a car.
  • Rental Cars: Car rentals are readily available here, providing flexibility to visit nearby attractions and enjoy the scenic beauty of the region at your own pace.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft operate in the area, offering quick, reliable transportation whenever needed.
  • Bicycle Rentals: For a more active way to discover the destination, bicycle rentals are accessible, allowing you to soak in the local sights while enjoying the fresh air.

Local Customs Options

  • Ashland's Arts and Theater Traditions: You will notice a strong local emphasis on arts, with community events celebrating theater and visual arts that showcase the region’s creative spirit.
  • Respect for Natural Environment: The area encourages eco-friendly practices and outdoor etiquette, ensuring visitors help preserve its scenic beauty and natural parks.
  • Coffeehouse and Local Food Culture: You can enjoy the laid-back vibe here by indulging in locally brewed coffee and farm-to-table dining, reflecting community hospitality and sustainability.
  • Festival Celebrations: Participating in seasonal festivals and events is a cherished custom that highlights the region’s vibrant community life and cultural pride.

Frequently Asked Questions About Ashland?

1. What are the top vacation rentals in Ashland?

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

2. How many vacation rentals have private pools in Ashland?

There are 6 vacation rentals with private pools near Ashland. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Ashland are best for families?

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

4. How many Rentbyowner vacation rentals are available in Ashland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 458 in the Ashland 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 Ashland. 

5. What is the cancellation policy for vacation rentals in Ashland, Oregon?

Cancellation policies vary by property and owner. It is essential to review the specific listing details or contact the property owner directly to understand the refund options and any cancellation deadlines before booking your stay.

6. Are there any minimum night stay requirements when booking a vacation rental here?

Minimum stay requirements can differ depending on the property and the season. To ensure availability and to meet the owner's policies, please check the specific listing details or reach out to the host prior to booking.

7. How do I contact the property owner if I have questions about my reservation?

You can communicate with the property owner through the messaging system provided on the booking platform. For any urgent concerns or additional inquiries, it’s recommended to contact the owner directly via the contact information listed in the property profile.

8. What amenities are typically included in vacation rentals in this area?

Amenities vary among listings but often include essentials like Wi-Fi, kitchen facilities, and parking. To confirm that your desired features are available, review the detailed property description or speak with the owner before finalizing your reservation.

9. Is there a cleaning fee or other additional charges for staying in these vacation rentals?

Additional charges such as cleaning fees, service charges, or taxes are common and should be clearly outlined in the listing description. Always review the total cost and ask the owner if you have any questions about extra fees before completing your booking.