Holiday rentals with a fire pit in Ashland

Refined, Serene Home in Jacksonville

Professionally decorated in a Mid-Century Modern style. Sleep soundly on Hungarian down pillows and BeautyRest Black mattresses made up with soft 600 thread-count Italian linens. Beautifully tiled bathroom offering Turkish towels, bathrobes, and luxe sundries. Living room and full kitchen with gas stove and quartz counter tops. Step outside to a private yard with outdoor eating area and cozy fire pit. Other amenities include three flat-screen Smart TV's, cable, WIFI, washer and dryer and so much more. Come and enjoy! You'll have this complete private cottage to yourself with private (and ample) parking. Come and go as you please in complete privacy. Self Check-in Available I'm available, if needed. I typically give a complete walk through of the property. For busy travelers, special arrangements can be made to stock the kitchen with additional supplies such as eggs, juice, special drinks. Our goal is to provide you with wonderful service. Let us know how we may help you have a terrific stay. The house is set in a laid-back neighborhood with a mix of shopping and dining within walking distance to Jacksonville's historic core. Ashland and Oregon Shakespeare Festival are a 15 minute drive away. 9% City Guest Tax will be applied to nightly rate & any additional charges. Tax is billed at arrival and must be paid via cash or check before departure. Airbnb is not allowed to collect this tax in advance.

Cozy Family Ranch Cottage! Near Vineyards & Lake!

Welcome to Guches Ranch! Nestled on a picturesque ranch established in 1964 by the Guches family, a vast expanse of lush farmland. Our Airbnb listing is the ultimate retreat for those seeking solace and serenity away from the hustle & bustle of city life. We are located centrally to local popular Vineyards in the serene Applegate Valley, just 12 miles outside the historic Jacksonville Oregon. Our brand new modern-style single cottage is a stand alone unit & is a private cozy, yet spacious haven.

Angel Crest Casita Guest Suite - East Medford

Enchanting, large, private 1 bedroom guest suite with a view In Upper East Medford. Beautiful, open concept living /dining area has plenty of room to relax and unwind. This space also includes a semi private queen bed. There is a large luxurious shower, kitchenette, and other amenities (microwave, fridge, and coffee maker). Outside there is a large private covered deck with outside seating and a fire pit. Close to wineries, golf, restaurants, and great hiking. This is a non smoking property.

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

The Birdhouse Retreat| Views & Hot Tub

Take it easy at this unique and tranquil getaway. Immerse yourself with the sound of the forest gazing at the Applegate valley and lavender farms below. Walk around in over 10 acres of forest and enjoy a forest bath and sounds of the river below. Minutes from renowned Applegate Valley wineries and Applegate lake. Snow capped mountains in view most of the year. This space has a private bedroom and bathroom with a separate entrance. For the chilly nights, enjoy a cozy fireplace and a movie.

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!

New Barndo: Stunning Rogue River access!

Escape to our chic one-bedroom retreat with stunning Rogue River access, blending luxury and serenity. Fish, raft, or relax by the river with wine or coffee in hand. The spacious bedroom boasts a king-size bed with plush linens, while the cozy living area offers a queen sleeper sofa. Cook with ease in the fully equipped kitchen featuring stainless steel appliances. Perfect for a tranquil getaway, this riverside haven awaits. Book now to experience the Rogue River’s breathtaking beauty!

Private & Cozy Treetop Cabin in Jacksonville

Welcome to your private cabin up in the trees, just 3 miles from sought after Historic Jacksonville, Oregon-where award winning restaurants, wineries, and adventures await! Set among mature Madrones and Pines with views of the evergreen mountains and lots of fun wildlife, you will be using all your senses to discover what Oregon is all about. A well behaved pet not left alone is welcome with approval. Message for 1 night stays or dates not listed. Thanks for looking! 🌄🌲🪾🦌🌌

Claudia's Retreat Sanctuary

Retreat here on my 6 acres of madrone forest with pastoral views, 2 meditation labyrinths- yet only 3 miles to the quaint, historic town of Jacksonville, Oregon, home of Britt Festival, 35 minutes to Ashland and 1.5 hours to Mt. Shasta or Crater Lake. This guest suite in the lower level of my house. Walk the spiral labyrinths. Book a Sacred Sound bath session with Tibetan and crystal bowls & Paiste gongs for $70 during your stay. Massage chair available too. Simply divine!

Stylish home with private access to Rogue River!

With breathtaking views of the Rogue River, our stylish one bedroom rental offers the perfect blend of luxury and tranquility. Spend your days fishing, rafting, or simply lounging by the water with a glass of wine. The bedroom features a king-sized bed with plush linens, and the living area has a comfortable twin trundle bed. The kitchen is fully equipped with stainless steel appliances and all the essentials. Book your stay now and discover the beauty of the Rogue River!

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.