Holiday rentals in Jackson County

Riverfront Retreat w/Pool, Hot Tub, Mountain Views

Soak in riverfront & mountain views from the hot tub or private balconies at this luxury 10-acre retreat! 3BR/4BA with 2 master suites, plus a separate pool house with its own bath — sleeps up to 12. Enjoy the pool, gravel paths to the river, and total privacy on the property. Ideal for extended stays (30+ nights) — perfect for relocations, remote work, or seasonal getaways. Interested in a shorter stay or your desired dates aren’t available? Message us directly to check availability and rates.

Starlight Meadow Yurt

The yurt is a modern, light, space with a deck. It's nestled between a mixed conifer forest and Starlight Meadow. We're at the end of a private road on 20 acres. The property is gated for your comfort and peace of mind. There's a large trampoline at the edge of the meadow perfect for stargazing and sunsets. The creek flows October thru June depending on rainfall. Six miles from Shady Cove where you'll find restaurants and a grocery store. 40 miles to Crater Lake. 26 to Ashland. Treat yourself!

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.

Country Garden Cottage

Newly remodeled Garden Cottage with living area/kitchenette, bedroom, and bathroom. Cottage has high ceilings, ceramic tile floors, quartz countertop, cherry wood cabinets and new mini-split heater/air conditioner. It is bordered on two sides by a garden common area with seating, fountain, and a grape vine covered pergola. New Roku TV installed. Conveniently located: * 5 min to I-5 * 10 min to airport * 3 min to Central Point * 10 min to Medford * 5 min to Jacksonville * 25 min to Ashland

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.

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 Shady Knoll

Relax and Unwind at this peaceful retreat. Near the Rogue River, this beautiful property is over an acre w/ lush green grass all around. Updated home w/ nice features & a notable primary bedroom&bathroom. Both rooms have work spaces & home has excellent wifi ~ 200mbps. Start your mornings with a delicious nespresso and enjoy the bird chirping outside. Outdoor oasis with comfy patio seating and outdoor dining area, backyard lights, fire pit, BBQ, and yard games. Close to TONS of outdoor fun!

Hill House at Double Day Ranch

Located in the foothills of the Cascades, just east of historic Butte Falls, Double Day Ranch is the ideal spot for your multi-family wilderness getaway. A relaxing retreat with views of pasture, barns, wildlife, and beautiful stars. Explore the Sky Lakes Wilderness, swim in Willow Lake or Fish Lake, hike Mt. McLoughlin or take a day trip to Crater Lake. All this while enjoying premium accommodations including king size memory foam beds, comfortable living spaces and high-speed internet.

Aviator-Themed, Fastest WiFi, 2 King Beds Home

Book 30+ nights and receive a ★ FREE ★ $100 Gift Card to any Rogue Valley restaurant! Beautiful Rogue Valley listing - 1,475 sq/ft! ★ Covid-19 Friendly ★ Our cleaners have been trained on the proper use and application of PureGreen 24, an EPA-approved, non-toxic cleaner that provides 24-hour residual protection. ★ ★ Close to Wineries and the Rogue Valley Country Club ★ ★ ★ ★ Less than 4 Miles to Downtown Center ★ ★ ★ ★ Great Views of RoxyAnn and the Siskiyou Mountains ★ ★

Ripple Rock Lodge- Gateway to Crater Lake

The Ripple Rock Lodge offers amazing views of The Rogue River Gorge and Lost Creek Lake. The lodge has a large patio with ambient lighting, and both gas and charcoal grills! It is located on a 10 acres parcel of woodlands to explore with access to the Rogue River and numerous hiking trails. Medford International Airport is approximately 40 miles from the Lodge and Crater Lake National Park is approximately 35 miles. Now offering as a wedding venue, please message with any inquiries!

Rogue River Lodge, Riverside Cabin

One of the Upper Rogue's most popular private cabins along the Rogue River. Cabin built in 1937 & recently refurbished with all of modern conveniences - family & pet friendly, with large deck overlooking the Rogue River. Private cabin located just steps from the Rogue River - fully equipped cabin, with private hot tub and dry/moist sauna. Only 52 miles to Crater Lake National Park, with local fishing, rafting, hiking, wineries, golfing & more.

Luxurious Station House Suite A

Step into the lavishly detailed space of the Jacksonville Station House Suite A, with private rooftop views and chic elegance throughout. This Station House unit has two bedrooms, two bathrooms, Smart TVs, an incredible rooftop patio, high ceilings and sunny views. The full kitchen takes center stage here, bold and opulent, a joy for any chef yet a short walk to shops and restaurants.