Discover a selection of 227 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 swimming pools and WiFi. Prices start at $57 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.
Top rated rentals — Ashland
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 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.

What are the top vacation rentals in or near Ashland?

The heart wants what the heart wants, and right now it's craving a vacation. Now's the time to pack your bags and zip off to one of these top vacation rentals in or near Ashland:

  • "Red Blanket Cabin Near Crater Lake National Park" is a hit with guests. Around 40 miles from Ashland, it has 2 bedrooms and lots of amenities to help you feel at home, including a firepit and cookware, dishware and utensils.
  • "Stone's Throw Bungalow ~ Walk To Plays" also promises an awesome stay, offering 1 bedroom, a washing machine, a nearby laundromat and more. It's around 1 mile from Ashland.

For even more great options, use the search bar at the top of the page to find the perfect Ashland vacation rental for you.

What are the best tiny house vacation rentals in or near Ashland?

You need only set foot into one of our tiny house vacation rentals in Ashland to discover that good things really do come in little packages. Designed to maximize every square inch of space, these pint-sized pads promise a big vacation experience:

  • Take a few days off to clear your mind at "Cozy Tiny House Small But Mighty". Located in Central Point, WiFi and a microwave oven are just a couple of the amenities included here.
  • Alternatively, make yourself at home at "Cabin - Modern Tiny House In The Woods W". Situated in Shady Cove, this little gem comes with a fridge and a nearby river.

What are the top-rated vacation rentals for weekend getaways in or near Ashland?

Escape from the rat race at one of our weekend getaways in or near Ashland. Whether you'd like to hang out with buddies or spend treasured time with the fam, there'll be something to suit your style. Try these top-rated properties on for size:

  • "Large Private Carriage - House Retreat With Amazing Views" is perfect for one or two days of R&R. It features a range of amenities, such as a restaurant dining guide and nearby museums, and is located around 11 miles to the northwest of Ashland.
  • Otherwise, make new memories with your loved ones at "Craftsman Style Home In Country Setting", which is around 4 miles to the northwest of Ashland. Take advantage of an ice maker, off-street parking options and more here.

Can I find studio apartments for rent in and around Ashland?

Studio apartments may be small, but they sure pack a punch when it comes to convenience and location. Plonk your bags down at one of these terrific studio apartments in or near Ashland:

  • One of our favorite properties is "Stone's Throw Bungalow ~ Walk To Plays". Book a few nights at this popular abode and you'll have access to a boat and a water park.
  • Or, use "Quiet, Modern, Cottage" as a base to explore the best sights around you. This home away from home offers a washing machine, nearby hunting activities and more.

Can I find short term rentals in or near Ashland?

Whether you're searching for a compact apartment just for you or a villa that'll fit the entire family, short-term rentals are easy to find in and around Ashland. These properties make a comfortable base for a whirlwind visit:

  • For an awesome weekend away, settle in at "Large Private Carriage - House Retreat With Amazing Views". It's close to the center of Ashland, along with countless things to see and do.
  • Another great choice is "Craftsman Style Home In Country Setting". Gather your favorite people and enjoy a comfy stay close to the heart of Ashland.

What are the best romantic weekend getaways in or near Ashland?

Forget roses and chocolates. Sometimes all you need is a weekend away, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Ashland that would make Cupid green with envy. Here are some we think you'll love:

  • Around 1 mile from Ashland, "Stone's Throw Bungalow ~ Walk To Plays" is the perfect place for starry-eyed lovebirds. Winery tours and beauty services are among the many amenities you'll find here.
  • Another option where you can enjoy a few magical days together is "Quiet, Modern, Cottage". Located 11 miles from Ashland, beauty services and winery tours add to the ambiance here.

What are the best large group vacation rentals in or near Ashland?

Big groups mean huge fun. They also mean finding a place that'll easily fit your whole gang. Browse our large group vacation rentals in or around Ashland and spend time with your favorite people under the same roof:

  • You'll have enough space to spread out at "Bookstayhop - The Pioneer North And South". Around 0.1 miles northeast of Ashland, this generous property has 5 bedrooms accommodating up to 14 guests. Amenities include a kitchen and a TV.
  • Invite as many as 12 of your friends to "Bookstayhop - Redtail Suites ~ Entire Home" and fill the place with love and laughter. This popular option has 4 bedrooms and is around 1 mile to the southeast of Ashland. It's packed with features to keep your group comfortable, such as a garden and mountain views.

What are the best houses for rent with a pool in or near Ashland?

Of all the amenities a vacation rental can offer, a pool delivers the most fun. Take a peek at these houses for rent with a pool in or near Ashland and spend your time splashing around. Just remember to take your flamingo floatie:

  • Get into vacay mode at "Hanna's House - Your Home Away From Home", where your highest priority will be lounging by the pool. Amenities including a separate dining area and a DVD player help make this getaway a favorite with guests.
  • Otherwise, put your bags down and your feet up at "Shady Cove River House - Fly Fish". In addition to its inviting pool, you'll also have use of towels and childrens activities.

Ashland has a mediterranean climate, with average summertime temperatures ranging from 45 ºF to 80 ºF. But you don't have to wait until summer to visit. Take a look at the search bar at the top of the page and adjust the filters to find the ideal Ashland vacation rental and plan your escape for whenever you like.

What are the best large family vacation rentals in or near Ashland?

The first mission of any big family trip is finding the perfect place to stay. Whether you're organizing a break with the kids or a reunion with all your relatives, we've got large family vacation rentals in and around Ashland that'll fit everyone. Here are two popular options worth considering:

  • With 4 bedrooms sleeping up to 10 guests, "Craftsman Style Home In Country Setting" gives you space to reunite with family or friends. It's around 4 miles northwest of Ashland and features amenities that'll keep your group content, such as a microwave oven and a dishwasher.
  • Another excellent option is "In The Historic Railroad District". It's about 0.1 miles to the east of Ashland, has 4 bedrooms and accommodates up to 8 guests. Useful amenities here include a separate dining area and free toiletries.

If you'd like to visit some family-friendly attractions around the area, Cole M. Rivers Hatchery is a fun outing for all ages.

Can I find family cabin rentals in or near Ashland?

Cozy up with your kiddos in a family cabin rental in or near Ashland and get ready to build some incredible new memories together. Here are some we think you'll love:

  • "Creekside Cabin - - A Quiet, Wooded Country Delight" - This popular place offers a toaster and a fridge and is around 7 miles northwest of the center of Ashland.
  • "Cabin - Bookstayhop - #51 And #52 Hyatt Prairie Compound" - Another awesome choice, this cabin comes with coffee and tea making facilities, a smart TV and more. You'll find it around 12 miles to the east of Ashland.

For more options, use the search bar at the top of the page and adjust the filters to find the Ashland vacation rental that's perfect for your needs.