Holiday rentals in Roxy Ann Peak

Cute Boho w Patio, W/D, Parking (No Chores!)

Top floor of house is all yours with private exterior entrance. The first floor is a separate unit with separate entrance. Fast Wifi + Kitchen + Privacy + Outside Deck! Welcome to our charming, boho unit, nestled on the entire, private second floor of this historic 1937 home. A perfect getaway for couples, small families, and business travelers alike -- private entrance and deck. Explore the scenic Rogue Valley, indulge in local wineries, and enjoy a comfortable stay in this picturesque gem

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.

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

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.

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.

Romantic 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.

Historic 1875 Kitchen House

Easy walking distance to Britt concert venue, trails, and downtown. The base rate is for the entire first floor and includes one bedroom with en suite bathroom with a large clawfoot tub. Upstairs attic space can also be rented for an additional fee, which includes 3 beds and a full bathroom. Declare 3 guests if 2 people need their own suites. If you are checking in with 4 or 5 people, please indicate the true number of guests, which adds an extra fee per person to cover cleaning costs.

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.

Kelly’s Farm 4 miles to Ashland

Nestled on the border of the Shakespeare hamlet of Ashland, Oregon, is Kelly’s farm. Only four miles away from Ashland. Kelly’s farm has horses, goats, chickens, gardens, fruit and nut trees with views of Mt. Ashland’s seven-thousand feet high profile in its front and bucolic rolling hills in its back. Bring your dog! You have access to a large fenced in yard right from your private entrance and deck. ***Unfortunately we are not set up for children under 4 or kitty cats.

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.