Destination guide

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?"

Things to do

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?

Activities

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.

Weather

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.

Natural features

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."

How to get there

Transportation options to and around Ashland

The nearest airport is in Medford, OR (MFR-Rogue Valley Intl.), 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 can also fly into Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away.

Where to stay around Ashland?

Our 2019 property listings offer a large selection of 205 vacation rentals near Ashland. From 56 Cabins to 85 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Ashland for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Ashland?

HomeAway offers a large selection of vacation rentals near lovely places in Ashland. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Lithia Park: 260 vacation rentals
  • Southern Oregon University: 259 vacation rentals
  • Oregon Shakespeare Festival: 261 vacation rentals
  • Ashland Library: 260 vacation rentals
  • North Mountain Park: 261 vacation rentals

But there are many other points of interest around Ashland listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Cabins in Ashland?

Yes, of course. HomeAway has 56 Cabins in Ashland. Our other popular types of vacation rentals in Ashland include:

  • Houses: 85 rentals available
  • Cottages: 56 rentals available
  • Bungalows: 56 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Ashland?

Yes, you can select your preferred vacation rental with pool among our 6 vacation rentals with pool available in Ashland. Please use our search bar to access the selection of vacation rentals available.