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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

Modern Tiny House w/ Hot Tub and Putting Green

Located on a hillside in Shady Cove. This is a spacious brand new 300 sq foot tiny home. The tiny house is located on our private property. We request for our guests to be respectful of our home, our neighbors, and surroundings. It is important that our guests treat the outdoor space as if they were camping and not leave any food outside as there is some wildlife in the area. Included is a covered gazebo with curtains on a private deck with a spa, and gas fire pit that also heats your legs.

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.

Luxurious Hobbit Hole and Second Breakfast!

If you want to experience the comfort of a hobbit hole in a beautiful setting, this is your next destination! From the moment you walk through our round doors, you'll be pampered with rich furnishings, a cozy king-sized bed, spacious shower, plush bathrobes and unique details. Second breakfast is included! Inspired by Meriadoc Brandybuck (Merry to his friends), it features the rich tones of Meduseld and the wood and stone of Fanghorn forest. Make sure to check out all four hobbit holes!

Peach Orchard Cottage

Quaint cottage nestled in a fruit orchard, near the beautiful Trinity river. The cottage is set in a quiet pastoral setting that borders always green pastures. There is a seasonal garden lot by the House as well as an orchard where guests can pick fruit in season, surrounded by a view is of the breathtaking forested Trinity Mountains. Come enjoy the fresh air and clear stars! We are also cleaning the cabin using the CDC - Airbnb cleaning protocol to ensure the safety of our guests!

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.

The Emerald Outpost - off-grid gateway to SRNF

Get into the wild! Private, remote, off-grid. Our cozy cabin sits on 12 acres of forest property and is surrounded by Six Rivers National Forest land without a neighbor in site. You'll be just steps from a crystal clear private swimming hole in year-round Jones Creek. Drive 2 miles to picturesque swimming holes on the wild and scenic Smith River. If you love the idea of unplugging to enjoy the wilderness in all its natural glory, consider this unique getaway!

The 'Easy A' Cabin in Rocky Point

Welcome to The Easy A Cabin! This stylishly updated 1960s cabin is our beloved mountain retreat. The Easy A is located in Rocky Point and minutes from Rocky Point Resort, Harriman Springs Resort, and Lake of The Woods. Nearby activities include hiking, kayaking, climbing Mt. Mcloughlin, fishing, Crater Lake Zipline, and Crater Lake National Park is less than an hour away. Visit the best-kept secret in the Southern Cascades in comfort and style.

Ashland tiny home with view and barrel sauna

Vaulted 8.5x20 craftsman tiny home built in 2023. Large wrap around deck overlooking the hills of Ashland. Stunning space to reset, relax and enjoy. Five minutes to downtown ashland. Great bird watching. Fall asleep to the sound of crickets on a comfortable queen bed in the upstairs loft. BBQ out on the deck, with all new amenities. Mini split heat pump and shared barrel sauna. We hope you enjoy the space as much as we do.