Ashland vacation rentals

We found 298 vacation rentals — enter your dates for availability

Discover a selection of 100 homes, 58 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:Feb 13 - Feb 20

Image gallery for Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Welcome to the Ashland Lavender Estate view from the hot tub
9.8 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Ashland, OR

8% off
Price is $862
$6,035 for 7 nights
All fees included
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

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Find out more about Ashland

Top attractions in Ashland

Ashland, Oregon, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a rich cultural experience. Explore beautiful lakes, visit modern colleges and universities, and enjoy urban parks that cater to a variety of interests. Whether you're traveling solo, with family, or friends, Ashland promises an unforgettable getaway filled with exciting attractions and natural beauty.

  • Southern Oregon University: A modern campus bustling with city vibes, Southern Oregon University offers a vibrant atmosphere with beautiful architecture and a variety of cultural events. You'll find students engaged in a range of activities, making it a lively spot to explore.
  • Lithia Park: This urban park is a family-friendly gem in Ashland, featuring lush greenery, walking trails, and serene ponds. Perfect for a leisurely stroll or a picnic, the park provides a peaceful escape while still feeling connected to the city.
  • Howard Prairie Lake: A picturesque lake surrounded by stunning scenery, Howard Prairie Lake is ideal for outdoor lovers. Enjoy beach activities, fishing, or a romantic sunset by the water's edge, making it a perfect getaway for nature enthusiasts.

Things to do recommended for couples

Planning a romantic getaway in Ashland? Enjoy skiing together at Mount Ashland Ski Area, savor exquisite wines at Paschal Winery just 5 miles away, or take an adventurous ride on the Ariel Ski Lift. Each experience promises to create unforgettable memories for you both.

Things to do recommended for families

Families can unwind at Howard Prairie County Resort, enjoying its serene atmosphere. For a fun adventure, head to Rogue Valley Family Fun Center, just 16 miles away, where excitement awaits. Additionally, Howard Prairie County Recreation Area offers more relaxation and outdoor activities for everyone.

Things to do recommended for groups

Experience the magic of the Oregon Shakespeare Festival for an evening of culture and entertainment. For adventure lovers, hike the Bull Gap Lower Trailhead and enjoy stunning scenery. Don't miss the Lithia Artisans Market for a taste of local business and city vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking with Vrbo is simple

Are you hoping to cut costs on your next adventure? Being flexible with your travel dates can help, as prices often vary. Additionally, booking an extended stay can lead to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental.

In fair Ashland, where we lay our scene...

Best known for its world-class Shakespeare festival, this welcoming city has a super-arty college vibe, and feels smaller than it is, in a good way. An Ashland vacation rental gives you the kind of high culture that leaves the other theatrical hotspots sulking into their interval drinks, but it also does a fine line in brewpubs, quirky eateries, lively nightspots, and intrepid outdoor adventure. Not only that, but folks here are so friendly that you can understand why the thru-hikers from the Pacific Crest Trail are so reluctant to leave. After all, "what is the city but the people?"

Is this a Shakespeare festival I see before me?

In Ashland, "the play's the thing," and the Oregon Shakespeare Festival is an Ashland institution. For the last 80 years, it's been staging the best of the Bard along with up-to-the-minute works from more modern writers. It runs between February and November, putting on a heap of plays across several venues. Less famous, but just as good, is the Ashland Independent Film Festival. And if all that sounds like a bit too much sitting down for you, how about taking a stroll in the city's pride and joy, Lithia Park, or getting hands-on at ScienceWorks museum?

To Ashland or not to Ashland, there is no question

Though a good chunk of vacationers are in town for the theater, Ashland offers plenty of outdoor activities too. It's a much-loved R&R pit-stop on the Pacific Crest Trail, which accounts for the more extreme examples of beards and boots mixed up among the thespians. Water activities feature almost as prominently, especially rafting, kayaking, and fishing on the Rogue River. And when the snow comes, you can be sure that it won't be a winter of discontent for the daring souls shooting down the slopes at Mount Ashland Ski Area.

Shall I compare thee to a summer's day, O Ashland?

A "more lovely and more temperate" choice than an Ashland vacation rental is going to be a tall order. Sure, the odd dump of snow in the winter will leave those mountain tops "whiter than new snow upon a raven's back," and there's the occasional summer day when "too hot the eye of heaven shines," but generally the weather in Ashland is as refined as the city itself. Ashland tends to escape the worst of the North West's famous rain, but as the man himself said, "sometimes hath the brightest day a cloud." So bring a raincoat.

A vacation! A vacation! My kingdom for a vacation!

Thanks to its location in the foothills of the Siskiyou and Cascades mountains, the landscapes round Ashland are nothing short of spectacular. Rushing rivers, vast forests, and snow-capped peaks are the order of the day. To the south, you've got Siskiyou Mountain Park, with Mount Ashland an obvious point. Closer in to Ashland, it's more about the fields and orchards, and after all that nature, you might decide to sample the produce of one of the local vineyards. For as we all know, "good wine is a good familiar creature, if it be well used."

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?
When planning a vacation in Ashland, Oregon, one of the best areas to consider for your stay is the Historic Railroad District. This charming neighborhood is known for its unique character, featuring beautifully preserved buildings and a vibrant arts scene. Staying here puts you within walking distance of the Oregon Shakespeare Festival, a top attraction that draws theater lovers from all over. Additionally, you'll find delightful local shops, cafes, and galleries that make exploring the area a true pleasure.

Another excellent option is the Ashland Creek area, which offers a serene environment with close proximity to the lush Ashland Creek Park. This area provides an excellent blend of natural beauty and convenience, making it easy to enjoy outdoor activities while still being just a short distance from downtown. There are numerous vacation rental properties available here, allowing for a range of options to fit your needs.

For those who appreciate a more tranquil atmosphere, the neighborhoods surrounding Lithia Park are highly recommended. This expansive park is a major highlight of Ashland, featuring beautiful gardens, walking paths, and even a duck pond. Staying near Lithia Park gives you easy access to its scenic trails and the opportunity to enjoy various outdoor events and festivals throughout the year.
How much does it cost to rent a vacation home in Ashland?
Prices for vacation rentals in Ashland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ashland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ashland vacation house rentals?
You can find great discounts on house rentals in Ashland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Ashland ski resort rentals?
For ski resort rentals near Ashland, Oregon, travelers should consider the proximity to Mount Ashland, located about a 30-minute drive from the city. In the surrounding areas, particularly along the Ashland Ski Area Road, visitors can find cozy cabins and vacation homes that cater to winter sports enthusiasts. These properties often feature amenities such as wood-burning fireplaces, ski storage, and outdoor decks with stunning views of the surrounding mountains.

In Ashland itself, there are various rental options ranging from charming bungalows to modern apartments, many of which include fully equipped kitchens and spacious living areas, great for relaxing after a day on the slopes. The town is known for its vibrant arts scene and proximity to the Oregon Shakespeare Festival, providing a unique blend of cultural experiences alongside outdoor activities.

Additionally, rentals in the nearby town of Talent offer more rural settings, where visitors can enjoy peaceful environments with access to hiking trails and natural beauty. Many of these properties come with amenities like hot tubs, fire pits, and expansive yards, ideal for families or groups looking to unwind after enjoying winter sports or exploring the local area.
What is the most popular type of vacation rental accomodation in Ashland?
In Ashland, vacation houses are the most popular type of accommodation, with around 123 available in and around the city. These rentals are typically located in charming neighborhoods and offer spacious layouts, making them ideal for families or larger groups. Most vacation houses come equipped with full kitchens, multiple bedrooms, and outdoor spaces like decks or gardens, great for enjoying the area's natural beauty.

Apartments follow as the second most common option, with about 44 rooms available. These are often found in the downtown area, close to the Oregon Shakespeare Festival and local dining spots. Travelers can expect amenities such as modern kitchens, cozy living areas, and convenient access to local attractions.

Cottages, numbering around 37, provide a quaint alternative, often situated in quieter areas. These tend to have rustic charm and may include features like fireplaces and outdoor seating, ideal for a peaceful retreat.

Additionally, there are about 19 cabins and several chalets available, which offer a great experience for those looking to immerse themselves in nature.
Are there any family house rentals in Ashland?
In Ashland, Oregon, there are numerous family-friendly vacation rentals available, with about 105 options to choose from. The charming neighborhoods of Ashland offer a variety of spacious homes, ideal for families looking to enjoy a comfortable stay. Many properties feature ample living spaces, fully equipped kitchens for family meals, and outdoor areas for kids to play. Some rentals even come with amenities like private patios and game rooms, great for family gatherings after a day of exploring.

This locale is well-known for its vibrant arts scene and is home to the famous Oregon Shakespeare Festival, making it an excellent destination for culture enthusiasts. Additionally, the picturesque Lithia Park provides beautiful trails, playgrounds, and picnic areas, enhancing the family experience. See all family-friendly rentals in Ashland.
Can I rent a vacation home with a pool or hot tub in Ashland?
In Ashland, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, known for its vibrant arts scene and proximity to the stunning Rogue River, offers a variety of accommodations that cater to relaxation and leisure. Many of these properties are located in picturesque neighborhoods surrounded by nature, providing a serene backdrop for your stay.

Travelers can expect amenities such as private pools, outdoor hot tubs, spacious patios, and fully equipped kitchens, making these rentals great for families or groups looking to unwind after a day of exploring. Additionally, some homes may offer access to beautiful gardens or outdoor living areas that enhance the overall experience. Find your rental in Ashland with a pool or a hot tub.
Can I find long-stay vacation rentals in Ashland?
A long-stay vacation rental in Ashland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Ashland?
In Ashland, travelers can find a variety of pet-friendly house rentals, with over 100 options available to accommodate different group sizes and preferences. Many of these rentals are equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, making them ideal for families or groups traveling with pets.

The neighborhoods surrounding the downtown area are particularly appealing, offering easy access to local parks and the renowned Lithia Park, which features scenic walking trails, picnic areas, and beautiful gardens that are superb for enjoying time with pets. Additionally, the vibrant downtown scene is pet-friendly, with a number of cafes and shops that welcome dogs, enhancing the overall experience for visitors traveling with their furry companions. See all pet-friendly rentals in Ashland.
Are there any remote work vacation rentals in Ashland?
In Ashland, Oregon, there are plenty of remote work vacation rentals available, with around 176 options to choose from. This vibrant town is renowned for its arts scene, including the famous Oregon Shakespeare Festival, making it a culturally rich environment conducive to both work and leisure. Many of the properties come equipped with dedicated workspaces, such as desks and ergonomic chairs, alongside high-speed Wi-Fi, ensuring a productive remote working experience.

Travelers can expect amenities that cater to their needs, including comfortable living areas, kitchen facilities for preparing meals, and some rentals featuring additional comforts like outdoor patios or gardens for relaxation after a day of work. The proximity to local coffee shops, parks, and scenic trails adds to the appeal, allowing for enjoyable breaks in between work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Ashland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ashland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Ashland?
In Ashland, popular vacation rental amenities include WiFi, kitchens equipped for cooking, coffee and tea makers for morning brews, blenders for smoothies or soups, and patios for enjoying the outdoor scenery.
When is the best time to visit Ashland for a vacation rental?
The best time to book a vacation rental in Ashland is during the peak season from June to August, particularly in July. This vibrant period attracts numerous culture enthusiasts eager to immerse themselves in the renowned Oregon Shakespeare Festival, which showcases world-class performances in a picturesque outdoor setting. The warm summer temperatures, typically ranging from the mid-60s to mid-90s Fahrenheit, create an inclusive setting for both outdoor adventures and leisurely strolls through the charming streets of downtown Ashland.

During the peak months, you'll find a lively buzz throughout the town, great for those who enjoy socializing and engaging with fellow travelers. From hiking in the nearby Siskiyou Mountains to enjoying the local culinary scene, there's no shortage of activities to keep you entertained.

For those looking for a more budget-friendly experience, consider visiting in December. While the temperatures are cooler, averaging in the low 30s to mid-50s Fahrenheit, this month offers a unique charm with fewer crowds and a chance to experience the local holiday festivities.

Ultimately, whether you prefer the bustling energy of summer or the peaceful, festive spirit of winter, Ashland presents a wealth of opportunities to create memorable experiences.
How early should I book a Ashland vacation rental?
Book your Ashland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ashland?
In Ashland, Oregon, visitors can explore a variety of attractions centered around its vibrant arts scene and natural beauty. The downtown area is famous for the Oregon Shakespeare Festival, where travelers can enjoy world-class performances in multiple theaters. This region also features charming boutiques, cafes, and galleries, making it a lively hub for culture and entertainment.

Nearby, Lithia Park offers stunning landscapes with walking trails, duck ponds, and beautiful gardens, superb for outdoor enthusiasts. The park is located just a short stroll from the downtown area, allowing easy access to both nature and the city's amenities.

For those interested in wine, the surrounding Rogue Valley is home to numerous vineyards and wineries, offering tastings and tours that showcase local varietals.
Can I change or cancel my Ashland home rental booking on Vrbo?
To find Ashland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Ashland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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