158 Ashland Holiday 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 holiday rentals from 5 rental sites including HomeAway, TripAdvisor, Booking.com and more, from $54 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

Looking for the perfect vacation rental for your Ashland getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Ashland offers 159 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 121 properties with high-speed internet, 17 full with jacuzzi and pool, and homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $2385 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Ashland has 159 gorgeous homes with 31 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 5 rental sites in Ashland where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 93 HomeAway rentals, 29 TripAdvisor short term rentals and 21 Booking.com vacation rentals.