Best Resorts and Rentals in Ashland 【 EXCLUSIVE 】Rent By Owner

Ashland Resorts

Resort

Lithia Springs Resort

8.8

Fabulous

(551 Reviews)

10 Baths 27 Guests 457.47 ft²

US $199/Night 7 Nights - US $1,393

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Highly Rated

Resort

Green Springs Inn

9.2

Exceptional

(129 Reviews)

1 Bath

US $109/Night 7 Nights - US $762

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Resort

Green Springs Inn

8.3

Excellent

(141 Reviews)

13 Baths 52 Guests 536.54 ft²

US $99/Night 7 Nights - US $691

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Resort

Bayberry Inn and Retreat

1 Bath

US $222/Night 7 Nights - US $1,556

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Highly Rated

Cottage

The Ashland Cottage, walk to town

10.0

Exceptional

(226 Reviews)

1 Bedroom 1 Bath 4 Guests 600 ft²

US $256/Night 7 Nights - US $1,795

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House

Swank House on Main St in Ashland

10.0

Exceptional

(5 Reviews)

2 Bedrooms 2 Baths 4 Guests 1496.18 ft²

US $527/Night 7 Nights - US $3,689

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Price Dropped

Hotel

Best Western Windsor Inn

9.0

Exceptional

(1004 Reviews)

1 Bath

US $124/Night 7 Nights - US $868

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Hanna`s House | Downtown Retreat, Steps to OSF

Highly Rated

House

Hanna`s House | Downtown Retreat, Steps to OSF

10.0

Exceptional

(170 Reviews)

1 Bedroom 1 Bath 4 Guests 495 ft²

US $300/Night 7 Nights - US $2,097

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House

Grandview of Ashland

10.0

Exceptional

(4 Reviews)

1 Bedroom 3 Baths 6 Guests

US $961/Night 7 Nights - US $6,728

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Highly Rated

House

The Perfect Vacation Cottage

10.0

Exceptional

(119 Reviews)

2 Bedrooms 2 Baths 4 Guests 1000 ft²

US $541/Night 7 Nights - US $3,789

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Pioneer Vacation Rentals - Pioneer South downtown Ashland

House

Pioneer Vacation Rentals - Pioneer South downtown Ashland

10.0

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 8 Guests 1194.79 ft²

US $126/Night 7 Nights - US $882

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Highly Rated

House

The Red Dragon House

10.0

Exceptional

(110 Reviews)

2 Bedrooms 1 Bath 4 Guests 1000 ft²

US $182/Night 7 Nights - US $1,272

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More Top-Rated Resorts in Ashland Area

Why Choose Rent By Owner for your Ashland Resorts?

What makes our Resorts special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Ashland Resorts

Where are the best neighborhoods to stay in Ashland?

When visiting Ashland, Oregon, exploring neighborhoods like the historic downtown or the charming Lithia Park area can enhance your stay. These locations offer easy access to local amenities and a vibrant cultural scene, making them ideal for travelers seeking convenience and comfort. Choosing accommodations in these neighborhoods ensures you experience the best of Ashland, Oregon

Historic Downtown District

Staying near the Historic Downtown District allows you to enjoy the area's vibrant arts scene and charming shops, making it an ideal choice for exploring Ashland's cultural heart.

View 200+ Rentals in Historic Downtown District

Historic Railroad District

The Historic Railroad District offers a unique glimpse into Ashland’s transportation history, providing easy access to scenic views and local attractions in the region.

View 52+ Rentals in Historic Railroad District

Siskiyou-Hargadine Historic District

Choosing accommodations here places you within a neighborhood rich in historic charm, perfect for immersing yourself in Ashland's early 20th-century architecture and community spirit.

View 27+ Rentals in Siskiyou-Hargadine Historic District

Skidmore Academy Historic District

This historic district is renowned for its elegant homes and educational heritage, offering a serene setting that complements your stay in Ashland's distinguished neighborhoods.

View 332+ Rentals in Skidmore Academy Historic District

Best Times to Visit Ashland

When should you plan your Resorts stay?

To make the most of your stay, consider visiting during the shoulder seasons when this destination offers pleasant weather and fewer crowds, ensuring a more relaxed experience while exploring the region's charming resorts and natural beauty.

Peak Season Highlights

Summer (June to August)

During the warm summer months, you'll experience the region's vibrant outdoor scene at its best. This is the ideal time for exploring local events and enjoying extended daylight hours.

Average Temperature Daytime: 75-85°F - Nighttime: 50-60°F

Fall (September to November)

Autumn brings colorful foliage and a lively cultural atmosphere, making it a popular season to visit this destination for scenic beauty and local festivities.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F

Off-Season Highlights

Winter (December to February)

The winter months offer a quieter experience, with fewer visitors and a peaceful environment perfect for relaxing stays in this area’s cozy resorts.

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

Spring (March to May)

Early spring provides a quieter period before the peak tourist season, with blooming landscapes that make it a lovely time for a tranquil getaway in the region.

Average Temperature Daytime: 55-65°F - Nighttime: 35-45°F

Weekly Weather Forecast for Ashland

How to Book Your Ashland Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

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 Resorts in Ashland Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts 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 spacious outdoor decks or patios ideal for relaxing and dining amid scenic views.
Take advantage of private gardens or landscaped yards perfect for outdoor leisure activities.
Make use of outdoor fire pits or fireplaces to gather with family and friends during cool evenings.
Benefit from access to hiking trails or nature paths directly from the property, allowing easy exploration of the area.
Use outdoor seating areas designed for socializing and enjoying the fresh regional air.
Discover amenities like swimming pools or hot tubs that provide relaxation after a day exploring here.
Utilize covered porches or sunrooms that extend your living space outdoors, ideal for enjoying the region’s climate.

Top Attractions Around Ashland

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor pursuits such as hiking, exploring scenic trails, and experiencing local cultural events that highlight the area's vibrant arts scene, all just moments from your stay in the area’s welcoming resorts.

Family Activities

Oregon Shakespeare Festival: Enjoy engaging performances that captivate audiences of all ages and immerse your family in local culture at this renowned theater.
Lithia Park: Explore scenic walking trails, picnic spots, and playgrounds within the lush surroundings of this iconic park nestled in the heart of the city.
ScienceWorks Hands-On Museum: Interactive exhibits and hands-on activities make learning fun and engaging for children and adults alike in this family-friendly science museum.
Ashland Skatepark: Spend active afternoons skating and bonding as a family at this popular skatepark designed for skaters of all skill levels.

Adult Activities

Wine Tasting Tours: Discover the region’s renowned vineyards and enjoy guided wine tasting experiences that showcase local winemakers' craftsmanship.
Historic Downtown Strolls: Explore charming streets lined with unique boutiques, art galleries, and cafes that reflect the area's rich cultural heritage.
Theatre Performances: Attend world-class plays and performances at local theatres to immerse yourself in the vibrant arts scene of this destination.
Nature and Scenic Hikes: Take advantage of scenic trails and outdoor excursions that highlight the natural beauty surrounding this region, perfect for leisurely walks or more adventurous hikes.

Other Places to Stay in Ashland, OR

Ashland Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead for Seasonal Events: Be sure to check the local event calendar so you can schedule your stay around popular festivals and performances that showcase the area's vibrant arts scene.
Explore Local Dining Options: Take advantage of the region's farm-to-table restaurants and cozy cafes to enjoy authentic flavors during your visit.
Discover Scenic Outdoor Activities: Make the most of the natural surroundings by planning excursions like hiking or cycling in nearby parks and trails.
Choose Strategic Accommodation Locations: Selecting a resort close to key cultural venues and outdoor attractions will maximize your experience here and reduce travel time.

Transportation Options

Rental Car Services: Conveniently explore the area at your own pace using local rental car agencies that offer a wide selection of vehicles tailored to your travel needs.
Public Transit: The regional transit system provides an affordable and eco-friendly way to navigate around the region, connecting you to nearby attractions and amenities.
Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber and Lyft are readily available here, offering quick and reliable transportation for your adventures.
Biking and Walking: With scenic routes and pedestrian-friendly streets, cycling and walking are excellent ways to immerse yourself in the local atmosphere of this destination.

Local Customs Options

First Friday Art Walk: You can experience this vibrant local custom where galleries and studios open their doors for art enthusiasts each month, showcasing the region's thriving arts scene.
Festival of Light Parade: During certain seasons, the community celebrates with a festive parade featuring illuminated floats, reflecting the area's creative spirit and holiday traditions.
Ashland Shakespeare Festival: This longstanding tradition attracts visitors from around the world to enjoy world-class performances in the region’s renowned outdoor theaters.
Farmers Market: Supporting local producers, you’ll find this lively market offering fresh, seasonal produce and artisanal goods, embodying the region’s commitment to sustainability and community.

Frequently Asked Questions About Ashland Resorts

1. What are the top Resorts 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 Resorts in Ashland:

2. How many Resorts are available in Ashland?

Currently, the total number of properties listed by RBO in 2026 is over 4 in the Ashland area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Ashland. 

3. What is the cancellation policy for resorts in Ashland, Oregon?

Cancellation policies vary by property. You should carefully review the specific resort listing details or contact the owner directly to understand the terms and potential fees involved.

4. Are there any special amenities available at resorts in this region?

Many resorts offer a range of amenities such as spa services, outdoor activities, or on-site dining. Check each listing for detailed information about the amenities included during your stay.

5. How do I ensure my reservation at a resort in Ashland is secure?

Reservations are typically secured through the official booking process on the listing page. For added security, confirm the hotel's policies and consider reaching out directly to the owner if you have specific questions.

6. What are the check-in and check-out times at resorts here?

Check-in and check-out times are set by individual properties. Review the listing details or contact the owner to confirm the designated times for your stay.

7. Is there a minimum stay requirement when booking a resort in this area?

Minimum stay requirements can vary depending on the property and season. To avoid any surprises, always verify this information in the property listing or contact the owner before completing your reservation.