Holiday rentals in Medford

Luxury Guest House in Charming Old East Medford

Nested on a great oak-canopied street in Old East Medford’s most charming neighborhood, where leisurely walks and turkeys abound, our professionally designed guest home combines authentic Swiss detailing with distinctive features of new and reclaimed materials. A chef’s kitchen and spa-like bath, complete with a soaking tub, towel warmer, and radiant floor heating, create a luxurious retreat. Perfectly situated to explore Southern Oregon, near wineries and trails, we’d be delighted to host you.

Orchard Home Cottage *Private• Cozy• Peaceful*

*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

Manor Hill Haven | Hot Tub & Accessible Features

This single level 2-bedroom, 2-bathroom home is ideal for families, couples, or business travelers and has accessible features. Located in a residential only neighborhood, this property offers modern conveniences w/ comfort & style close to Medford medical plazas. - Handicap Accommodative & Wheelchair Accessible - EV Charger with access to a single-car garage for parking - Large Deck with mountain views - Hot Tub - .5 Mile to Golf Course - 1 Mile to Asante - 0.4 miles to Rogue Valley Manor

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.

The Cutie Little Local

The Cutie Little Local is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with new appliances, and extra special little touches, will make your stay easy and enjoyable. Whether your main destination is Medford, or perhaps you plan to visit nearby cities like historic Jacksonville or Ashland, the CLL is a great point of access for all. Numerous restaurants, hiking trails and wineries are nearby allowing an eventful trip to the beautiful Southern Oregon.

Suite Comice EV Charging

*NOTE*: We disinfect all surfaces before and after new guests arrive. Studio suite with private entrance. Comfortable, light, clean and airy. Host on location in attached home. Breakfast nook with coffee, and tea. Neighborhood is quiet with shopping and dining not far away. Only one small step into the unit. Also on the property is another 2 bedroom Airbnb unit, Comice Valley Inn, in the event you have a larger party. This is a new listing, so please see some of my many 5-star reviews.

W/D, FULL Kitchen, Downtown walking , Parking

Comfort and convenience in this chic lower-level guesthouse, perfectly located just moments from downtown. Within easy walking distance of restaurants, shopping, farmer’s market, parks, and public transit — the best of the city right at your doorstep! Take advantage of a kitchen stocked with all the essentials for preparing home-cooked meals, and washer and dryer for extended stays. Queen bedroom, plus sleeper sofa comfortably accommodates up to 4 guests. Fast, reliable Wi-Fi

The Peak Loft (Tesla Charger)

The Peak Loft: A peaceful space to recharge above the Rogue Valley. Designed for slow mornings and intentional living, this 1-bedroom retreat blends clean lines with calm energy. Stretch, sip coffee, and reset before exploring with our curated local guide list or optional wellness, self-care, and snack kits. Includes EV charging, full kitchen, workspace, and laundry; just steps from our newest city park and minutes from everything. A stylish basecamp for every direction you roam.

Clean, comfy, pet friendly & fully stocked

Relax at Casita Blanca! Peaceful, fully stocked and tons of extra amenities for your enjoyment. Perfect for families, girls trips, dogs, and right off of I-5 if you’re passing through and need a place to rest your head. Extra care has gone into curating this home including a lavish coffee and tea bar, robes, house socks (socks are for you to keep), comfy beds, luxury amenities, pup basket, wifi, smart TV's in every bedroom, kids items, and a fully stocked kitchen.

Southern Oregon Gem (EV Charger)

Welcome to our charming little home in Medford, Oregon. a delightful haven designed for comfort, cleanliness, and efficiency. Nestled near the city center, this inviting space offers a perfect blend of coziness and functionality for a memorable stay. The thoughtful layout maximizes every inch of space, creating a welcoming atmosphere for solo travelers, couples, or small groups. The color palette is soothing, creating a serene ambiance that promotes relaxation.

Cozy Cottage

Discover this charming gem nestled in the heart of Medford, Oregon! This enchanting 1 bedroom with a king bed and 1 bathroom cottage is a centrally located and offers the perfect blend of comfort and style. The sofa in the living room is a hide-a-bed which can sleep 2 additional people. Conveniently located near shopping, restaurants, and more! For the safety and security of our guests, we do have an outdoor camera monitoring common areas.

The Epic A - Charming 1960s A-Frame w/Hot tub

Introducing The Epic A, an A-frame style home in the Southern Oregon countryside minutes from downtown. This charming space is perched on a hillside with a view of the local mountains, a hot tub, and everything you need to enjoy your visit to Grants Pass. The hosts have taken special care to balance vintage style with modern comforts and create a relaxing atmosphere. Expect quiet evenings and wildlife visits on this beautiful acre property.