Family-friendly holiday rentals in Medford

Cozy cottage in old E. Medford

Your family will be close to everything when you stay at this centrally-located home. Minutes from shops, restaurants, parks, hospitals, hikes, rivers & more. The kitchen & bathroom are freshly gutted, renovated & updated. The master has a brand new cozy king mattress. The black out shades in both bedrooms makes for a nice nights sleep. Lots of games for your family fun. Smart tv and Wi-Fi available. Cute little back patio with BBQ & yard access. Includes full laundry room with an extra fridge..

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

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.

The Cutie Little Loft

The Cutie Little Loft is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with brand 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.

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.

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.

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

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.

Eco-Tiny House in SE Medford

Clean and quiet 200 sq ft. detached guesthouse with kitchenette nestled among vegetable gardens and native wildflower beds. Within walking distance of Asante hospital and several shops and restaurants. Easy access to freeway. 20 minutes from downtown Ashland and Jacksonville and only and 10 minutes from downtown Medford. Off-street parking available. Well-behaved pets welcome. Please no smoking inside the guesthouse or on the property.

Designer Home w/ Chef’s Kitchen

Stunning designer home with a true chef’s kitchen, perfect for families, couples, remote workers, wedding parties, and four-legged friends. Thoughtful high-end finishes throughout, sleeps 7 comfortably with lightning-fast WiFi. Close to gorgeous Rogue Valley wineries, Britt trails and outdoor adventures. Less than 10 minutes from historical downtown Jacksonville and The Britt Festival!