Holiday rentals with a fire pit in Medford

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

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!

Brookdale Meadows Farmhouse Cutie

Farmhouse charm on a quiet residential street. Home has 3 bedrooms, (4 beds), 2 baths, (walk in shower) eat in kitchen, formal dining room, family room, formal living room, laundry room, covered deck, and more… Close to parks, golf course, jet boat tours, wineries, shopping, easy access to I-5 and just 4 miles from Medford Airport. Ashland Shakespeare Festival and Historic Jacksonville just 20-25 minutes away. Crater Lake, Oregon Coast, Redwoods, and Portland all make great day trips.

Top Comfort! King Bed, Pets OK, Firepit & WiFi

A Modern Millennial Dream Getaway Step into your next Insta-worthy escape! This bright, stylish home blends bold design with cozy comfort — perfect for making memories and snapping shareable moments. The open-concept living room features a stunning, floor-to-ceiling hand-painted mountain mural and a warm gas fireplace, creating the ideal backdrop for relaxation or your next photo op. Every space is thoughtfully curated for guests of all ages, offering a playful yet peaceful retreat.

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! 🌄🌲🪾🦌🌌

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.

🐞 Tiny Living At It’s Finest - Ladybug 🐞

Feel refreshed when you stay in this rustic gem! Nestled in the mountains on Old Stage Road, this tiny home will be your cozy, peaceful retreat away from it all. Important note on directions: Google Maps has recently been directing guests to the neighboring property with a brown gate. Our entrance is just less than 100 yards south of that, and our gate is open and silver. Please make sure to check the house numbers carefully — we are directly on Old Stage Road.

Keene Way Hideaway

Welcome to Keene Way Hideaway, your perfect getaway! This charming 3-bedroom home offers a serene escape with all the comforts you need. The real gem of this property is the oasis backyard – a private haven where you can unwind amidst lush greenery, and a relaxing patio area. Whether you're looking to explore the local attractions or simply relax in your own slice of paradise, Keene Way Hideaway is the ideal destination for your next vacation.

Comfy Cozy Casa

Relax with the whole family at this comfy and clean family friendly home centrally located in a cute residential neighborhood. Only minutes away from major shopping, food, and entertainment. This location makes for an easy stop over along I-5 on an Oregon road trip. Hiking trails are not far from this location, many guests stay here to check out Crater Lake National Park, and even some of the mountain lakes not far away.