Ashland vacation rentals

We found 279 vacation rentals — enter your dates for availability

Discover a selection of 131 homes, 49 apartments, and other vacation rentals in Ashland that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you need and want for your stay, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Ashland

Showing deals for:Nov 7 - Nov 14
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Find out more about Ashland

Find out more about Ashland

Why visit Ashland

  1. Outdoor Adventures: Enjoy a variety of outdoor activities including hiking, biking, and exploring picturesque lakes and parks.
  2. Vibrant Arts Scene: Experience Ashland's rich cultural atmosphere with lively downtown, art galleries, and the renowned Oregon Shakespeare Festival.
  3. Family-Friendly Activities: Engage in numerous family-oriented excursions that cater to all ages, ensuring fun for everyone.
  4. Charming Accommodations: Choose from a range of delightful vacation rentals, from cozy cottages to comfortable apartments.
  5. Welcoming Community: Embrace the friendly locals and unique experiences that make Ashland a special destination.

Popular types of accommodation in Ashland

If you're looking for the perfect getaway in Ashland, you're in the right place! Our platform offers a variety of popular vacation rentals, including houses, charming cottages, and comfortable apartments. Whether you're searching for the best Ashland vacation rentals or house rentals in Ashland, we ensure transparency, savings, and reassurance for your stay. Discover the ideal accommodation for your next adventure to this beautiful destination!

  • Houses: These spacious, fully-equipped homes are the top choice for those seeking comfort and privacy during their stay in Ashland, ideal for families or groups.
  • Cottages: Charming and quaint, cottages offer a cozy retreat, perfect for travellers looking for a picturesque getaway.
  • Apartments: Conveniently located, apartments provide a modern living space, great for couples or solo adventurers wanting easy access to local attractions.
  • Cabins: Rustic and inviting, cabins allow guests to immerse themselves in nature while enjoying a home-like atmosphere.
  • Chalets: These alpine-style rentals blend comfort with scenic views, catering to those who appreciate a unique stay in the mountains.**

Top attractions in Ashland

Ashland, Oregon, is perfect for those seeking outdoor adventures and stunning scenery. Visitors can explore picturesque lakes, urban parks, and the vibrant college atmosphere. The area's attractions cater to those looking for romance and nature experiences. To make the most of your trip, consider exploring nearby destinations to enhance your vacation and immerse yourself in the beauty of the region.

  1. Southern Oregon University: A vibrant campus with modern architecture, Southern Oregon University offers a lively atmosphere where you can experience city vibes while enjoying art exhibits and cultural events.
  2. Lithia Park: This beautiful urban park features lush gardens, walking trails, and playgrounds, making it a perfect spot for families to unwind while soaking in the outdoor and city ambience.
  3. Howard Prairie Lake: A picturesque lake perfect for romantic getaways, Howard Prairie Lake boasts stunning scenery, outdoor activities, and charming beaches for a tranquil escape.

Things to do recommended for couples

For a memorable couples getaway in Ashland, explore the snowy slopes at Mount Ashland Ski Area, enjoy a romantic wine tasting at Paschal Winery just 8.0km away, and embrace adventure on the Comer Ski Lift. Each experience promises unforgettable moments together!

Things to do recommended for families

In Ashland, families can relax at Lithia & Driveway Fields, enjoy adventure at the Rogue Valley Family Fun Center, or unwind at Howard Prairie County Recreation Area. Each spot offers a unique blend of wellness and fun, perfect for creating lasting memories together.

Things to do recommended for groups

Experience the enchanting Oregon Shakespeare Festival for a dose of culture and entertainment. Explore the Lithia Artisans Market for local crafts and flavours, or embark on an adventure along the Bull Gap Lower Trailhead, where stunning outdoor scenery awaits your group.

What do I need to keep in mind when booking a vacation in Ashland

When planning your trip—whether you're travelling with a group, family, pets, or seeking longer stays—it's important to prioritise your preferences. Here are some helpful booking tips for your Vrbo experience.

  • Traveling to Ashland with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for these options and more on Vrbo.
  • Traveling to Ashland with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Ashland: For many families, a getaway wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that both you and your four-legged friends feel comfortable and at home.
  • Planning for a long term stay visiting Ashland: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider additional features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Ashland

Ashland, Oregon, offers a delightful blend of outdoor adventure and vibrant culture. Explore the charming downtown, where lively nightspots and artistic vibes await. Enjoy gorgeous views of the surrounding landscapes and engage in family-friendly excursions. Nearby, you can find the warm atmosphere reminiscent of New Orleans, making Ashland a fantastic destination for budget-conscious travellers seeking unique experiences. Embrace the friendly people and diverse activities that make this region truly special.

  • Historic Downtown District: The Historic Downtown District of Ashland is a vibrant area brimming with charm and character. Known for its romantic atmosphere, this neighbourhood invites visitors to stroll along its tree-lined streets, exploring unique shops, art galleries, and cafés. The Oregon Shakespeare Festival is a major highlight, offering exceptional theatrical performances throughout the year. Outdoor enthusiasts will appreciate the nearby hiking trails and the stunning landscapes of the surrounding national and state parks, including picturesque lakes. Whether you're enjoying a family outing or a romantic evening, the Historic Downtown District is a must-visit destination.
  • Historic Railroad District: Nestled near the heart of Ashland, the Historic Railroad District is a delightful neighbourhood that captures the essence of the area’s rich history. This district is perfect for families and outdoor lovers, offering a blend of cultural experiences and recreational activities. Visitors can enjoy local theatres showcasing a variety of performances and explore the scenic hiking trails that wind through the region. The proximity to beautiful lakes and national parks allows for easy access to outdoor adventures, making it a great spot for those looking to enjoy nature while still being close to the comforts of town.
  • Siskiyou-Hargadine Historic District: The Siskiyou-Hargadine Historic District is an enchanting neighbourhood known for its stunning scenery and outdoor experiences. This area is particularly appealing for couples seeking romance amid its picturesque surroundings. Visitors can take in the views while enjoying a day of skiing or exploring local theatres. The district's close proximity to national and state parks, along with tranquil lakes, provides ample opportunities for hiking and outdoor exploration. With its charming atmosphere and variety of activities, the Siskiyou-Hargadine Historic District is an ideal spot for those looking to immerse themselves in Ashland's natural beauty.

Best time to go to Ashland

If you're planning a trip to Ashland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly SunnyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighSlightly Low
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June60.4°F (15.8°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
July69.3°F (20.7°C)No Rain (Dry)SunnySlightly HighSlightly High
August68.7°F (20.4°C)No Rain (Dry)SunnyAverageSlightly High
September61.5°F (16.4°C)No Rain (Dry)SunnyAverageAverage
October51.1°F (10.6°C)Light RainMostly SunnySlightly LowAverage
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December34.7°F (1.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for planning new trips, refining your existing plans, or managing your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The captivating area of Ashland awaits your stay

Enjoy the area's entertainment, theater scene and opera and make a vacation rental your home during your stay in Ashland. Travelers to this welcoming city praise the festivals, gardens and cafes. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Ashland

Do you want to find top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Ashland a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Mount Ashland Ski Area (7.8 mi / 12.5 km)
  • Centennial Golf Club (9.4 mi / 15.1 km)
  • Rogue Valley Country Club (10.6 mi / 17.1 km)
  • Paschal Winery (5 mi / 8.1 km)
  • StoneRiver Vineyards (7.5 mi / 12.1 km)
  • EdenVale Winery (9.3 mi / 15 km)

Exploring the gardens and other natural features in Ashland

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Ashland is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Lithia Park (0.5 mi / 0.9 km)
  • Emigrant Lake (6.3 mi / 10.2 km)
  • Howard Prairie Lake (16.1 mi / 26 km)
  • Applegate Lake (24.2 mi / 38.9 km)
  • North Mountain Park (0.7 mi / 1.2 km)
  • Roxy Ann Peak and Prescott Park (11.4 mi / 18.3 km)

Transportation to and around Ashland

The nearest airport is in Rogue Valley Intl. Airport (MFR), located 14.4 mi (23.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away.

Frequently asked questions

What is the best area to stay in Ashland when booking a vacation rental?
Historic Railroad District is one of the most sought-after neighborhoods to book a vacation property in Ashland. Stay here to enjoy the convenience and privacy that comes with having the whole place to yourself.
What is the most popular type of vacation rental accommodation in Ashland?
Houses are the most popular kind of vacation rental in Ashland, according to our data. Even if you have a different vision in mind, Vrbo has properties in many sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a vacation rental in Ashland?
Property type, season and length of stay are some factors that can determine the price of a vacation home. Simply add your travel dates to find your dream escape. From quaint country cottages to plush villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Ashland?
Prices for beach houses in Ashland may vary depending on the size and style of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to see your options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Ashland?
Yes, there are. You'll find 59 vacation homes that welcome pets in Ashland on Vrbo. Our furry friends need a break too, so simply use our search function for pet-friendly vacation rentals to find a property where Spot can lap up the good times.
What are popular rental amenities in Ashland?
Tennis, a barbecue grill and a firepit rank as the most popular rental amenities in Ashland. Whether you're planning to travel alone, with your sweetheart or a group of best friends, Vrbo will help you find a vacation rental that matches your tastes with all the features you'll enjoy.
Are there large group vacation rentals in Ashland?
Ashland has seven vacation rentals that can host 10 or more guests. These properties come with all the space you need to share good times with your favorite people.
Are there vacation rentals in Ashland that welcome kids?
With 59 family-friendly vacation homes to choose from in Ashland, now is the perfect time to introduce the kids to the wonders of travel. Simply click on our "Properties good for families" filter box to look for stays that feature conveniences perfect for vacationing families, like living rooms, yards, entertainment units and bunk beds.
What are the top attractions for families in Ashland?
Keep the kids entertained at these leading family-friendly attractions in Ashland:

  • ScienceWorks Hands-On Museum
  • Emigrant Lake
  • Bull Gap Lower Trailhead

Are there one-bedroom vacation rentals in Ashland?
Yes, there are 28 one-bedroom properties in Ashland to select from. A one-bedroom vacation home is a great choice if it's just the two of you or if you're flying solo. Toss in more space, convenience and privacy than a standard hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom vacation rentals in Ashland?
Ashland has 12 two-bedroom vacation rentals to choose from. Find a vacation home with all the space and privacy you're looking for at a price that won't break the bank on Vrbo.
Are there vacation rentals with WiFi in Ashland?
Ashland has nine vacation rentals with WiFi, so you'll be able to stay connected during your vacation. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to scrolling social media, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Ashland?
Decide on your travel dates and then use our filters to look for vacation rentals with ac in Ashland on Vrbo. With 56 air-conditioned properties on offer here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Ashland?
The minimum age is generally 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Ashland vacation rental before booking.
How long can I rent a vacation rental in Ashland for?
It all depends on the Ashland property. To see a list of options offering extended stays, just type your dates and number of guests into the Vrbo search page. Enjoy having the place to yourself, along with comforts such as air conditioning, a kitchen and a yard to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.
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