Barn holiday rentals in Southern Oregon

Carriage House Loft 5 acre Forest Retreat

1~In the forest on 5 private wooded acres… Alpine setting, gated entry, tastefully fully furnished, large covered deck. ~Long term Travel Nurse guests most welcome. The Loft is a large space with strong WIFI, well suited for working. Huge 1,200 square ft loft area is a wonderful retreat in the forest and features a board and batten, barn style OPEN FLOOR PLAN living space. 3 minutes to downtown Grants Pass Historic Shopping /Restaurant district and I-5. Private/quiet setting on a 5 acre lot

Charming very well appointed cottage !

The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 2 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If quiet is what you are looking for, the cottage will meet all your needs.

Crater Lake "Meadow House" near south entrance.

One of closest to Crater Lake (28.9 miles), Rogue River, Lost Creek Lake, 3 waterfalls, +100 ranch acres of woodland trails. Upscale creature comforts; 2-story, 2500 sq. ft., fully-renovated historic ranch home: hardwood floors, fireplace, large kitchen, 2 bedrms w/2 private baths +an xtra small sleeping room, views of mtns & meadows are spectacular. Enjoy the ranch & wildlife relaxing on wrap-around deck. Perfect for couples, small getaways & sm families (kids over 10),or a work away. No pets

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

Red Barn in Wine Country

New luxury barn with a rustic feel on "Red Barn Farm" in Southern Oregon Wine Country. Our five-acre micro-farm is situated on the Applegate River on the Applegate Wine Trail, a region of 19 artisan wineries. From barn, it's a 2 minute walk to the riverand the bridge to the world famous Red Lily Vineyard! This farmstay has a river swimming hole, friendly chickens, mini-goats & sheep, and a fire pit to spend dreamy evenings under the stars. Visit Wine Country Farm Stay dot com for more info!

Private, Restful, 5 Star Barn Apt

This apartment is a great retreat, and now available as a long term rental to traveling nurses and individuals working away from home at a monthly 30% discount off daily rate, or 15% off for weekly rate. It features an 18' high ceiling with 3rd floor loft BR; private covered deck overlooking an oxbow of the McKenzie River, access to 1.5 private acres with bbq, gazebo, and outdoor fireplace. WiFi, TV, Stereo, dishwasher, and private laundry; 15 minutes to local hospitals and U/O events.

ALL NEW!-Barnhaus-Spa+11 Acres+EV+Gym+Lake Access

The Barnhaus at Treetop Lodge—formerly The Studio—was completely and meticulously renovated for 2025. This handcrafted retreat sleeps 7 (2 kings, 1 bunkbed and a sofabed) with luxe TVs, a high-speed gaming PC, hot tub, firepit, EV Charging and gym. Set on 11 private acres with hiking trails through the forest that lead to a secluded lakefront. The private hot tub with string lighting is where rustic charm meets high-tech comfort—surrounded by nature and built for relaxation or play.

The Barn

Welcome to The Barn, a fully remodeled and reimagined 60's hay barn converted into "the best lil vacation rental in the valley". The Barn is located on the back of a large lot down a long driveway in a private setting. The side yard comes complete with a gas bbq and seating, surrounded by a tall fence for the ultimate privacy from any neighbors. The Barn is designed like a boutique hotel with all the creature comforts to make you feel like it is YOUR LIL BARN AWAY FROM HOME.

Gorgeous Lakeside HOUSE + Indoor SAUNA!

🌲 Luxuriate in this elegant barn home (with wifi) plus indoor *sauna.*🧖🏽‍♀️ You get the entire house + parking, all across from a lovely lake just 19mi east of downtown Ashland. Splurge on this Airbnb ‘Guest Favorite.’ Pet friendly! ✨Ask Laurel about hosting your special occasion here for extra deals.✨ 🛁 Relax. Walk the woods. Hike, bike, fish, cross-country skii. Head downtown to shop, socialize, catch a play, or just rest & restore. The choice is yours…