Where to stay around Ashland, OR?

Our 2019 property listings offer a large selection of 237 vacation rentals near Ashland. From 87 Houses to 49 Cabins, 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 VRBO.

What is the best area to stay when traveling to Ashland?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Ashland:

  • Historic Railroad District: 63 vacation rentals
  • Siskiyou-Hargadine Historic District: 106 vacation rentals
  • Historic Downtown District: 96 vacation rentals
  • Skidmore Academy Historic District: 61 vacation rentals
  • Mount Ashland Ski Area: 24 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Ashland?

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

  • Howard Prairie Lake: 184 vacation rentals
  • North Mountain Park: 271 vacation rentals
  • Oregon Shakespeare Festival: 273 vacation rentals
  • Emigrant Lake: 226 vacation rentals
  • Ashland Library: 273 vacation rentals

But there are many other points of interest around Ashland listed on VRBO 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 Houses in Ashland?

Yes, of course. VRBO has 87 Houses in Ashland. Our other popular types of vacation rentals in Ashland include:

  • Cabins: 49 rentals available
  • Cottages: 49 rentals available
  • Bungalows: 49 rentals available

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

Can I find a vacation rental with pool in Ashland?

Yes, you can select your prefered vacation rental with pool among our 17 vacation rentals with pool available in Ashland. Please use our search bar to access the selection of vacation rentals available.

    Nature and Shakespeare await in Ashland

    Less than a 2-hour drive from Crater Lake National Park, sits the stunning city of Ashland. The area attracts bikers, hikers, and outdoor enthusiasts of all types, thanks to its diverse terrain and impeccable views. Kids can enjoy the local hands-on museum, and parents can relax in the peaceful wine country. Those looking for entertainment are in luck, as Ashland’s Shakespeare theater is one of the most celebrated in the United States. The local art galleries are also a main attraction. With a warm summer and a winter that makes for comfortable skiing, Ashland vacation rentals are great for year-round family fun.

    Get in touch with nature in Ashland

    The city’s geographic diversity and natural beauty inspire more than a whole vacation’s worth of Ashland outdoor activities. Ashland has a variety of bike trails that range in both difficulty and terrain. For short rides, perfect for the whole family, try out the Tom Pearce Park Trail or the Rouge River Greenway Trail. The area’s topography also lends itself to incredible hiking trails. Follow a mapped route or take a guided tour. If you’re staying at Ashland vacation rentals for a romantic getaway, be sure to schedule a tasting at 1—or a few—of the area’s vineyards.

    Experience art and culture in Ashland

    Among the many natural wonders of Ashland is the famous Oregon Shakespeare Festival, a renowned theater featuring both the plays of the Bard and other works from approximately February to late October. If you are planning your Ashland vacation for the summer or fall months, you will have the opportunity to watch the Green Show, an open-air, free-of-charge performance. Ashland is also home to many art galleries, including South Oregon University’s Schneider Museum of Art. Kids will love Ashland’s ScienceWorks Hands-On Museum, which helps kids learn and play at the same time.

    Ashland’s Pleasant Climate

    Contrary to the typical rainy climate we tend to associate with Oregon, an Ashland weather map rarely shows rain. The city’s average number of sunny days is quite comparable to the national number. Winter temperatures generally do not go far below freezing, and the actual city sees little, if any, snow. But don’t worry if you’re looking to ski—the Mt. Ashland Ski Area is high enough up that it gets plenty of snow. Weather in the summer averages in the 60s and 70s, with highs above 80 during July. If you plan to do some hiking, it’s best to book your Ashland vacation rentals for the summer.

    The mountains and rivers of Ashland

    Skiers and hikers come from all around to visit Mt. Ashland, which has an elevation of 7,533 feet. In general, Ashland elevation measures just below 2,000 feet. While exploring the mountain, you can find the Ashland creek and other streams. Ashland Creek’s waters flow into Bear Creek, which flows into the Rogue River. Travelers can also take a day trip to Crater Lake National Park. Crater Lake, the deepest lake in the United States, impresses with its incredibly clear, blue water.