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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.

Peaceful Forest Cabin w/Cedar Hot Tub

Soak in a gorgeous cedar hot tub surrounded by forest. A quiet gem in the Siskiyou foothills, 15-20 min from Ashland’s Shakespeare Festival and Rogue Valley wineries. This craftsman tiny cabin sits above a seasonal creek with decks on two sides. Cozy loft bedroom, warm interiors, simple kitchenette. Wagner Creek trails steps away. Deer, turkeys, and occasional black bears visit. Eco-friendly throughout. Your restorative retreat awaits. We live on-site and love hosting but give you your space.

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.

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.

" sweet little garden studio "

Nice little shady deck with rocking chairs. Very quiet and safe little neighborhood. Great location. Eight minutes to downtown Ashland and 15 minutes to downtown Medford. Comfortable little Studio. Great for one or two busy guest. If bringing an animal please lmk beforehand of what kind and size. Im allowing one well behaved animal. Must not be left behind and clean up is a must. Thank you for understanding.

Artsy MCM Guesthouse w/ Spa Soaking Tub

2-Bedroom Guest Home - Perfect Stop-Over on Your Oregon Road Trip - Hot Tub - 2 Queen beds - Luxurious soaking tub - Gas fireplace - Walking distance to The Phoodery! - Private & Secluded - Tucked behind the front house for privacy - 1 mile from I-5 access - 7 miles to Ashland - 7 miles to Medford - Come explore the charming small town of Phoenix, Oregon - Nearby wine country for tasting and exploration