Discover a selection of 188 vacation rentals in Ashland, OR that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including kitchens and swimming pools. Prices start at $132 per night, and houses and cabins are popular options for a stay in Ashland. Either way, you'll find a rental for everyone's needs.
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?


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.

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.

How many vacation rentals are available around Ashland, OR?

Our 2020 property listings offer a large selection of 188 vacation rentals around Ashland. From 81 house rentals to 63 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Ashland?

Would you check out that view?! That's what you'll find yourself saying when you head for the hills and enjoy a glorious high-altitude getaway. Vrbo has no less than 61 mountain rental properties available. After a different setting? See if any of our other properties catch your eye. Our range here includes:

  • 32 city-center vacation rentals.
  • 24 rural vacation rentals.
  • 10 village vacation rentals.

Can I rent a house in Ashland?

If you're looking for a home away from home this trip, renting a whole house is a great idea. You and your crew will have loads of space for all your vacation activities. There are 82 houses listed on Vrbo. Prices start from $49 per night. If that doesn't match your posse's taste, we have a range of different property types to select from, such as:

  • Cottage: 64 vacation homes. Prices start from $33 per night.
  • Cabin: 22 vacation homes. Prices start from $175 per night.
  • Hotel: 22 vacation homes. Prices start from $58 per night.

Can I stay in Ashland in a large group?

Vacations with your favorite people can be stacks of fun, especially when you're sleeping under the same roof somewhere new! If you'll be traveling with a big group, Vrbo can help. At the moment, house vacation homes are the latest thing for large groups of travelers here, and we have 11 available on our database. The vacation rentals that can cater to large groups around here include:

  • If yours is a squad of 6, we've got 26 vacation homes perfect for that size. Stay a night for as little as $80.
  • After a rental property for 8 guests? We have 17 that will work well. You can book one for as little as $220 per night.
  • Seeking rental properties suitable for 5 guests? You'll be delighted to find out we have 16 that will fit the bill. You can bag one for as little as $95 a night.

You and the squad will be in good hands when you arrange your Ashland travels through us!

Where are the cheapest rentals in Ashland?

Tight hotel rooms are no place to spend your precious vacation moments! Uncover our budget-friendly rentals now and ensure everyone in your group has room to move. When it comes to seeking out an amazing deal, your first stop should be Skidmore Academy Historic District. Here, Vrbo has 55 rentals at an average price of $143 a night. Siskiyou-Hargadine Historic District is another good option. Vrbo has 108 rentals here, and the average price is around $183 a night.