Ashland vacation rentals

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Discover a selection of 124 homes, 56 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.
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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?
Among the most sought-after neighborhoods to book a vacation property in Ashland is Historic Railroad District. Find your perfect stay with Vrbo and explore this area as a local.
What is the most popular type of vacation rental accommodation in Ashland?
Cabins are the most popular type of vacation rental in Ashland, according to our data. Even if you have something different in mind, Vrbo has properties in loads of sizes and shapes. Explore our options to find your ideal match.
How much does it cost to rent a vacation rental in Ashland?
The average price for a vacation home in Ashland is based on several factors, like property type, length of stay and time of year. Whether you prefer a sprawling villa with space for extended family or a cozy condo ideal for just you and the kids, just add your dates of travel to discover stays that offer great value.
How much does it cost to rent a beach house in Ashland?
Prices for beach houses in Ashland may vary depending on the style and size of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filter tool to narrow down your search by amenities, ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Ashland?
With 168 vacation rentals that welcome pets, your furry little friend can join you on your Ashland vacation. Use the filter tool to search our pet-friendly vacation rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Ashland?
Check the “pool” box in our handy filter tool and you’ll find 10 houses with private pools in Ashland on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your leisure time is up to you when your Vrbo vacation home comes with its own swimming pool.
What are popular rental amenities in Ashland?
When it comes to rental amenities that guests are on the lookout for in Ashland, an electric car charging station, a barbecue grill and a garden are at the top of the list. With Vrbo vacation homes, you’ll enjoy options to match your taste and style, whether you’re going on a vacation with friends, relatives or even pets.
Are there large group vacation rentals in Ashland?
Ashland has 20 vacation properties that can accommodate 10 or more people. These stays come with enough space to share good times with friends and family.
Are there vacation rentals in Ashland that welcome kids?
Ashland has 166 family-friendly vacation rentals. And booking a stay that welcomes children is a cinch with our “Properties good for families” filter. On top of having the entire place to yourselves, you can also look forward to conveniences and perks like bunk beds, full kitchens and private pools.
What are the top attractions for families in Ashland?
Keep the kids busy at these leading family-friendly attractions in Ashland:

  • North Mountain Park
  • Mount Ashland Ski Area
  • Emigrant Lake

Are there one-bedroom vacation rentals in Ashland?
You’ll find 52 one-bedroom properties in Ashland to pick from. A one-bedroom vacation property is a great choice if it’s just two of you or if you’re vacationing solo. Add in more space, convenience and privacy than a hotel, and you’ve got yourself a getaway to remember.
Can I find two-bedroom vacation rentals in Ashland?
Ashland has 50 two-bedroom vacation properties for you to select from. Experience a vacation home with all the space and comfort you need at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Ashland?
Ashland has 41 vacation rentals with WiFi, so you can stay connected when you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to catching up on social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Ashland?
Pick your dates and then use the filters to locate vacation rentals with ac in Ashland on Vrbo. With 129 air-conditioned properties available here, you can enjoy a cool and comfy stay.
How old do you have to be to rent a vacation rental in Ashland?
The minimum age allowed can differ across properties on Vrbo, so double-check the rules of the vacation rental in Ashland you want to book. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Ashland for?
The length of time you can book a vacation rental in Ashland is down to the property. Just enter your chosen dates to display a list of options offering extended stays. With a range of amenities such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to get the perfect place to call your home away from home in Ashland.
Does Vrbo offer discounts for vacation homes in Ashland?
Short stay or extended escape, Vrbo has some fantastic deals and discounts in Ashland that’ll match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — without breaking the bank.

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