Skip to content
Sign up
Log in
Vacation rentals in Ashland

Vacation rentals in Ashland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Charming Guest House - One block from Downtown!
SUPERHOSTEntire guesthouse · 4 guests · 2 beds · 1 bath
Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

What guests are saying:

“This is a particularly well laid out space. They are attentive to small styling details. Loved the indoor plants. There were lovely fresh flowers on the kitchen table when we arrived. It is a space that feels loved and cared for. They put effort into protecting your privacy. And one of the nice bonuses about the sheltered private deck is it also shields you from a good portion of the wind. If you know Ashland, you will know how choice this location is. It's on a quiet street a couple of blocks from Lithia Creek and the plaza and the theater. What a gem.”

The Ashland Farm Cabin
SUPERHOSTEntire cabin · 2 guests · 1 bed · 1 bath
The Ashland Farm Cabin

Come stay on our beautiful farm just minutes from downtown Ashland. Enjoy gorgeous views of the East foothills and Mt. Ashland to the West.

What guests are saying:

“We had a wonderful stay at the cabin. Kym is doing a good job of making everything seem safe. My high level criteria for a stay is that it be clean, safe, quiet and have a good bed. All were met in this stay. It is a perfect stopping place when passing through Ashland (or I assume for staying in Ashland for a few days.)”

Clean, Stylish Apt w/kitchen. block from Downtown
SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
Clean, Stylish Apt w/kitchen. block from Downtown

92½ Church Street. A private apartment with a large bedroom, full kitchen, bath with shower. Vintage styling with loads of special touches, ONE BLOCK from downtown. All the comfort of home and so close to the action. Large yard. Permitted. (Ashland City Permit: 15-237). 2020 Update: We have adopted the recommended Covid-19 Cleaning Guidelines. We are also scheduling an empty day between guests, so the apartment can air out and we have time for a thorough cleaning.

What guests are saying:

“Leslie and Alan were super hosts, welcoming and helpful. The apartment was comfortable and calming. It is situated in a lovely neighborhood close to all our favorite Ashland Haunts. Leslie has created a restful get away haven. We can't wait to return.”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Ashland vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Ashland

30% off! Charming, walk to town.
SUPERHOSTEntire guesthouse
30% off! Charming, walk to town.
Price:$ 128 / night
Cozy camping close to town
SUPERHOSTCamper/RV
Cozy camping close to town
Price:$ 52 / night
Downtown Cottage - Great View and Discounted Rates
SUPERHOSTEntire cottage
Downtown Cottage - Great View and Discounted Rates
Price:$ 102 / night
The Aloha House ~ Pool and Hot Tub
SUPERHOSTEntire house
The Aloha House ~ Pool and Hot Tub
Price:$ 358 / night
Manzanita Cottage
SUPERHOSTEntire guesthouse
Manzanita Cottage
Price:$ 160 / night
Ashland Backyard Garden Studio
Entire guest suite
Ashland Backyard Garden Studio
Price:$ 33 / night
Summer's Night Cottage (1 BR Downtown Suite)
SUPERHOSTEntire guest suite
Summer's Night Cottage (1 BR Downtown Suite)
Price:$ 98 / night
Unique Private Room Downtown with Two Beds
SUPERHOSTRoom in boutique hotel
Unique Private Room Downtown with Two Beds
Price:$ 88 / night
Eco-Tiny House in SE Medford
SUPERHOSTEntire guesthouse
Eco-Tiny House in SE Medford
Price:$ 65 / night
Ashland French Country Villa w/exceptional views
SUPERHOSTEntire villa
Ashland French Country Villa w/exceptional views
Price:$ 250 / night
Ashland Carter House, Carriage House!
SUPERHOSTEntire apartment
Ashland Carter House, Carriage House!
Price:$ 129 / night
Sophisticated Downtown Suite
SUPERHOSTEntire guest suite
Sophisticated Downtown Suite
Price:$ 122 / night
Show all