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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.

Modern Farmhouse, Country Views

Unwind at this modern farmhouse built in 2022 & a 12-min drive to Ashland. Enjoy the private deck w/ views of mountains, valleys & vineyards. Two bedrooms w/ private bathrooms. Air-mattress available for extra guests. Great room has high ceilings, equipped kitchen & sitting area to enjoy the panorama. House is on a peaceful & secluded property in the hills above Talent. Shops/Restaurants minutes away. Easy access to OSF & centrally located for wine tasting & all activities in the Rouge Valley.

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

Wine Country Farm Stay Near Ashland

Stunning romantic wine getaway on a flower farm with spectacular views. Farm stay offers the perfect base for exploring the Rogue Valley wine trail, 15 minutes to over 20 Jacksonville and Ashland wineries in the heart of the valley. Cozy private deck offers a perfect spot to relax and enjoy wine with views of mountains, pastures, and fields. Home of the Oregon Shakespeare and Britt Festivals. One mile from the Greenway, a bike and pedestrian pathway. Enjoy a beautiful ride to local wineries.

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil tiny studio cottage. Perfectly located minutes off I-5 and just 3 miles from downtown Ashland—home to the Oregon Shakespeare Festival, Plaza shops, Lithia Park and restaurants. Explore Crater Lake, historic Jacksonville, and wineries in the picturesque Rogue Valley. Enjoy the privacy of our gated property with peaceful farm surroundings! Pets accepted with pet fee. No cleaning fee's for stays! Large parking lot for trailers and moving trucks.

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

5 Star Luxury Southern Oregon Suite

Great little getaway on the outskirts of town. Away from the hustle and bustle of the city center, but minutes away from all the great places the Rogue Valley has to offer. This 800 sq foot apartment has been completely renovated to meet all the needs of travelers that are looking for an overnight stay or a long term place to land. This space offers updated heating and air, strong wi-fi, separate bedroom and working space. 2 smart TV's, designated parking, and a private entrance.

Little Hooves Farm & Vineyard

Wake up and enjoy one of the most lovely views in the area. We live in a semi rural setting just 2 miles from downtown Talent and 6 miles from downtown Ashland, with beautiful views of the valley, surrounding hillsides, vineyards and our sweet little circus (farm). Our friendly goats, sheep, chickens, ducks, and pig will entertain you from afar. Watch the animals graze or nap in the sun while you sip your morning coffee or afternoon tea from the comfort of your own private suite.

Kick back and relax. Airstream with amazing views

Experience the perfect cozy getaway in this one-of-a-kind stay artistically rebuilt Airstream. Perched on its own terrace on a 5+ acre Italian style estate you'll be surrounded by spectacular views, an abundance of fine food, entertainment (including the world famous Shakespeare and Britt Festivals), nightlife, endless family-friendly and outdoor activities, day trips to destination wineries, redwoods and Crater Lake. 4 mi. from downtown Ashland and 13 mi. from Medford airport.

1910 Orchard Guest House

Set among open fields, mountain views, and grazing sheep, this beautifully remodeled 1910 Craftsman guest house offers a quiet, pastoral retreat in Southern Oregon. The home features a sunlit porch, full kitchen, laundry, and comfortable living spaces meant for settling in. The king primary bedroom and second bedroom with a full-size bed provide restful nights, with easy access to local wineries, hiking, rafting, and Ashland’s renowned theatre scene.

Luxury Modern Downtown Talent Millie Haus

The newly built modern Millie Haus has everything you need located just a block away from downtown Talent and nestled perfectly between Medford and Ashland. Enjoy the natural beauty of Southern Oregon home to wild rivers, gorgeous mountains and beautiful valleys. Wine lovers, hikers, bikers, fishers, and theater goers will love all of Southern Oregons natural beauty. Have a larger group? Rent the sister property next door, Parker Haus.

Ashland Artist Country Retreat

Lovely light-filled, artistic, private, quiet, two-level studio apartment with full bath and kitchenette located on an organic farm in a beautiful country setting, just 3.6 miles to downtown Ashland and the Oregon Shakespeare Festival. Enjoy a private garden and views of the trees and mountains, as well as original art made by your host. We offer organic and upscale amenities and use only eco-friendly and healthy cleaners.