The best rentals from the top sites, all in one place

We believe finding a vacation rental in Ashland should be easy and not take hours of searching and scrolling. We’ve designed VacationRenter from the ground up to help travelers find the perfect rental faster and easier.

Where to stay in Ashland

Vacation rentals in Ashland

There are 364 vacation rentals near Ashland for all manner or mood of travel, availability of time off, and size of budget. So, if you are hoping for an affordable Ashland vacation, you can find 10% rentals under $55/night. Or if you are willing to splurge on a luxury vacation in Ashland, there are 36 between $275 and $1,200/night. Whether you are sleeping by yourself or with a significant other, or are travelling with a group of 70 there are short term home and apartment rentals in Ashland to fit your Oregon vacation needs. The most popular types of short-term rental homes in Ashland are houses, private rooms and apartments. Ashland has been a frequently searched travel destination this year and continues to grow in popularity. VacationRenter offers a wide selection of vacation rental availability from leading travel sites like VRBO (Vacation Rentals By Owner), Homeaway,, and many more. Search your travel dates to find available Ashland vacation homes for your trip.

Where is Ashland

As the home of the famed Oregon Shakespeare Festival, Ashland is a charming mountain town with a laid-back vibe and some quaint vacation homes boasting incredible views. Consider these neighborhoods as you look for a place to stay in Ashland.

Quick Guide to Ashland

As a relatively small town, Ashland's neighborhood designations are somewhat informal, but they can still help you know which rental locations align with your vacation goals.
  • Shakespeare Blocks/Downtown: Located in the heart of everything, these neighborhoods are best for folks who are in town just to see some plays during the festival.
  • Above the Boulevard: Siskiyou Boulevard is a literal and figurative dividing line in Ashland. Houses "above" (to the northeast) the boulevard are generally tonier and offer better views, though they are farther away from the action in town.
  • Lithia Park: Though it isn't above the boulevard, this part of town balances upscale architecture with proximity to the Angus Bowmer Theatre.

Home-types in Ashland

Ashland has a variety of property types for you to consider when booking a trip. Here are the most popular property types in Ashland:
- House188 vacation rentals
- Private Room69 vacation rentals
- Condo36 vacation rentals
- Apartment36 vacation rentals
- Hotel21 vacation rentals

Points of interests in Ashland

Ashland has several popular points of interest for you to check out when visiting the area. Here are the most popular points of interest in Ashland:
- Weisinger Family Winery: 364 vacation rentals
- Ashland Parks & Recreation: 364 vacation rentals
- Irvine & Roberts Vineyards: 364 vacation rentals
- Garfield Park: 364 vacation rentals
- Grizzly Peak Winery: 364 vacation rentals
- Hunter Park: 364 vacation rentals
- Oregon Shakespeare Festival: 364 vacation rentals
- Schneider Museum of Art: 364 vacation rentals
- Oredson Todd Woods: 364 vacation rentals