House holiday rentals in Ashland

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, fireplaced open living room with an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, Britt Gardens, and more

Cute Boho w Patio, W/D, Parking (No Chores!)

Top floor of house is all yours with private exterior entrance. The first floor is a separate unit with separate entrance. Fast Wifi + Kitchen + Privacy + Outside Deck! Welcome to our charming, boho unit, nestled on the entire, private second floor of this historic 1937 home. A perfect getaway for couples, small families, and business travelers alike -- private entrance and deck. Explore the scenic Rogue Valley, indulge in local wineries, and enjoy a comfortable stay in this picturesque gem

The Cutie Little Loft

The Cutie Little Loft is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with brand new appliances, and extra special little touches, will make your stay easy and enjoyable. Whether your main destination is Medford, or perhaps you plan to visit nearby cities like historic Jacksonville or Ashland, the CLL is a great point of access for all. Numerous restaurants, hiking trails and wineries are nearby allowing an eventful trip to the beautiful Southern Oregon.

Street Level Flat in great Downtown Location "A"

This is a beautiful new 3 bedroom flat with oak hardwoods floors, granite counters, and new appliances. There is a laundry room with a washer and dryer. We offer a cozy living room to relax after your busy day with a sleeper sofa, flat screen TV, and air conditioning for those warm days. There is a fully equipped kitchen with stainless appliances, microwave and dishwasher. This flat is located in a prime location, a 5 minute walk to the popular Shakespeare Festival, restaurants and shops.

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Cozy Ashland Getaway

This bright two-bedroom ranch features a master bedroom with a king-sized bed and a smaller bedroom with a queen-sized bed. The living room is furnished with a couch and two comfortable chairs. The kitchen comes fully equipped, and the fenced yard is perfect for dogs. Enjoy a shaded front porch and a back deck ideal for watching sunsets. Interested guests can also inquire about including our 15-foot trailer in their reservation for an extra charge, which accommodates up to two people.

Beautiful and peaceful cottage close to downtown

Come retreat in our oasis during your stay in Ashland! Charming 1 bedroom, two bathroom home, tucked away from the busy boulevard, with a lovely outdoor space to relax in. Our cottage has a full kitchen, comfortable living space, and a pullout couch that converts to a full size, flexsteel mattress. Upstairs is a beautiful queen size bed with high quality linens, a sitting area, fireplace, and an office space. Each story is 500sf and filled with light from the abundance of windows.

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

Coyote Moon

Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.8 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island. Perfect for a romantic couples getaway and also great for those visiting Ashland for the Oregon Shakespeare Festival. NOTE: AFTER JULY 1ST, 2026, COYOTE MOON WILL NO LONGER BE AVAILABLE FOR BOOKING AS AN AIRBNB.

Charming house two blocks from downtown Ashland

The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comforts you will need. Cozy beds for sleeping late, a full kitchen with a complimentary coffee bar, a living room for socializing with family and friends, and all the privacy of having the entire property to yourselves. Restaurants, shopping, and theater begin two blocks away. This is the perfect house for your unforgettable Ashland experience.

Craftsman cottage built in 2019

One mile off interstate. This beautiful craftsman airbnb was built in 2019. and the attention to detail shows. Entire private house, large yard, washer/dryer, full kitchen, tiled shower, and upstairs with additional living space and bedroom. Close to Ashland, Jacksonville and Medford. Walking distance to the Phoodery, Clyde’s corner, and mini market. Space is not suitable for toddlers or elderly due to steep stairs leading to bedrooms.

Creekside Retreat Close to Town

You will be a 10 minute drive from Downtown Ashland and feel like you are out in the country. The home sits on 8 private acres and has river frontage and a beach on the year round Emigrant Creek. There are beautiful views in all directions of mountains, trees and wildlife. The home is a two story residential barn built in 2012 and remodeled in 2022 (the main living quarters is upstairs).