178 Ashland Vacation Rentals & Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Ashland vacation rentals from 5 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $33 to $740 a night.

Information about Ashland

About Ashland

A truly charming, Southern Oregon town, Ashland is known for hosting the annual Oregon Shakespeare Festival. Whether you’re a fan of the writer or not, you’ll certainly find fun and exciting things to do in this quaint town. From river rafting to wine tasting, there is a bit of something for everyone. Enjoy a day in Lithia Park which lies at the heart of the city. Whatever you choose to do, you’ll love this cozy town!

Things to do in Ashland

The most obvious thing to do in Ashland is attend the Oregon Shakespeare Festival. Luckily, the festival runs throughout the year from February to October, with events and plays on every day of the week except Mondays. Catch Henry IV, Cesar, and many more of Shakespeare’s classics. Take a backstage tour and learn how the shows all come together, or listen to a talk with Oregon Shakespeare Festival company members. You’ll be in good company, as this festival draws visitors from across the globe to experience the best of Shakespeare’s plays, talks, and tours.

River rafting in Ashland is a great outdoor adventure during your vacation. You can raft on the rapids at Rogue River, Upper Klamath River and Scott River. Choose a full day or half day trip, and go through companies like Indigo Creek Outfitters, Noah’s River Adventures, or Momentum River Expeditions. Indigo Creek Outfitters even offers trips that include a trip to a few local wineries and breweries for tastings. If you’d rather do your own wine tasting, head to Dana Campbell Vineyards where you can sip on reds and whites as you enjoy a gorgeous view of the mountains. Weisinger Family Winery is another excellent choice if you want to do some wine tasting, as is Belle Fiore Winery.

For a more leisurely experience in Ashland, head to Lithia Park which sits in the heart of downtown Ashland. Stroll through the 100-acre vista and you’ll see locals playing tennis, volleyball, or having lunch in the picnic areas. There is also playground equipment for the kids and a Japanese Garden within the park. Visitors can even take a guided tour of the park if desired. This park was designated as one of the top ten Great American Spaces by the American Planning Association in 2014, so make sure to stop in for a look.

Day Trips from Ashland

Drive southeast out of the city for about 25 miles and you’ll reach Cascade-Siskiyou National Monument. Established by President Bill Clinton in 2000, the monument is the first monument set aside solely for the preservation of biodiversity. Head to Pilot Rock and hike the remnants of an ancient volcano, climb to the top of Hobart Bluff and get a 360-degree view of the Rogue Valley, or go boating and fishing in Hyatt Lake. In early 2017, President Barack Obama expanded the Cascade-Siskiyou National Monument by around 48,000 acres, so there’s plenty of new land to explore!

Ashland Accommodations

Tripping.com offers every type of vacation rental you’re looking for in Ashland. Rent a whole Victorian-style house in downtown Ashland and stay a few minutes away from all the action of the Oregon Shakespeare Festival. Stay at an Inn and enjoy the free breakfast and perfect location in the heart of the city. Or, choose a quaint cottage on the outskirts of town for a romantic weekend getaway with a loved one.

There are plenty of restaurants and shops located conveniently in downtown Ashland. Try Morning Glory for breakfast or brunch, Luna Café + Mercantile for a pizza, and Blue Toba for a tasty Indonesian dinner. You’ll find jewelry shops, consignment stores, and gift shops dotted along Main Street in downtown Ashland. Go for a stroll and explore all that the town has to offer.

Transportation in Ashland

If you’re coming from out of state, you’ll want to fly into Rogue Valley International-Medford Airport. There are several shuttle options from the airport to Ashland, including Cascade Shuttle and Diamond Shuttle and Delivery. A rental car is a good idea if you plan on going on a day trip to Siskiyou-Cascade National Monument or doing any wine tasting in the area.

Vacation Rentals in Ashland

Find the best Ashland vacation rentals with Tripping.com. Choose from 177 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $33 a night to $740 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 130 of homes in Ashland offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 24 rentals with pool or jacuzzi, or relax with the family in one of the 98 homes with cable TV.

For all those dog lovers and cat lovers, Ashland offers 37 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 5 rental sites in Ashland where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 107 HomeAway rentals, 30 TripAdvisor short term rentals and 23 Booking.com vacation rentals.