Holiday houses in Jackson County

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Top-rated holiday rentals in Jackson County

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Top Guest favourite
The exterior of the unit is shown, featuring a private deck with seating and a view of the surrounding greenery. A well-maintained lawn is visible, along with flower beds and mature trees, which enhance the tranquil country setting.
Guesthouse in Medford
4.97 out of 5 average rating, 296 reviews

Mel-Ohana: your favorite country retreat!

Mel-Ohana is a quiet, private two bedroom, 1 bath upstairs unit with comfortable queen memory foam mattresses, kitchen amenities, and a beautiful large bathroom with tiled shower. Open, bright and airy, the country views are spectacular from both bedrooms. It's the perfectly-placed retreat, with Jacksonville/Britt 5 mins away, Ashland -25 mins., and 12 mins. from Medford shopping and restaurants. Wander the 1/2 acre lawn and garden area or share a bottle of wine on the ground-level cedar deck!

Top Guest favourite
A historic ranch home is set in a lush meadow adorned with wildflowers. A horse grazes peacefully nearby. The house features large windows and a spacious wrap-around deck, surrounded by towering trees, providing an idyllic natural backdrop.
Home in Prospect
4.97 out of 5 average rating, 222 reviews

Crater Lake "Meadow House" near south entrance.

One of closest to Crater Lake (28.9 miles), Rogue River, Lost Creek Lake, 3 waterfalls, +100 ranch acres of woodland trails. Upscale creature comforts; 2-story, 2500 sq. ft., fully-renovated historic ranch home: hardwood floors, fireplace, large kitchen, 2 bedrms w/2 private baths +an xtra small sleeping room, views of mtns & meadows are spectacular. Enjoy the ranch & wildlife relaxing on wrap-around deck. Perfect for couples, small getaways & sm families (kids over 10),or a work away. No pets

Guest favourite
A new tiny home is situated among tall pine trees, featuring a clean exterior with large windows adorned by flower boxes. A gas grill is positioned on a patio area, framed by a wooden fence and lush green grass.
Tiny home in Shady Cove
4.95 out of 5 average rating, 348 reviews

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.

Top Guest favourite
A cozy studio is nestled among tall pine trees, illuminated softly by warm outdoor lights. The clear night sky is filled with stars, adding a serene backdrop to the natural surroundings. A pathway leads to the entrance, inviting exploration of the tranquil setting.
Treehouse in Jacksonville
4.97 out of 5 average rating, 294 reviews

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.

Guest favourite
A bright bedroom features a spacious bed with neutral bedding layered with a green throw. Large windows allow natural light to fill the room, complemented by a ceiling fan. A wall-mounted TV is positioned above a modern desk area with a computer.
Home in Shady Cove
4.92 out of 5 average rating, 134 reviews

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!

Guest favourite
The cabin exterior is framed by lush greenery, with a vibrant orange facade contrasted by white windows. A wooden staircase leads up to a welcoming red door, surrounded by natural foliage, creating an inviting atmosphere within the forest.
Tiny home in Talent
4.94 out of 5 average rating, 120 reviews

Peaceful Forest Cabin w/Cedar Hot Tub

Welcome to our cozy cabin, nestled in Oregon’s lush forest beside a seasonal creek. Blending rustic craftsman charm with a bohemian flair, our cabin provides a warm ambiance with a well-equipped kitchenette , living room, and a walnut bar-top dining area. In the mezzanine loft, find an organic queen bed and a workspace with a fold-out futon. Enjoy our wood fired hot tub, Wagner Creek trails, nearby wineries and the Shakespeare festival, offering a mix of nature’s beauty and local culture.

Top Guest favourite
A spacious dining area features a large wooden table surrounded by six chairs. Natural light fills the room through two large glass doors that open to a deck with forest views. A bowl sits at the center of the table, adding a welcoming touch.
Home in Gold Hill
4.99 out of 5 average rating, 218 reviews

Hygge Hideaway. A home for rest and adventure

In Scandinavia, "hygge" represents contentment & coziness. Settle into this sun-soaked, mountain-side, madrone forest & valley view home for relaxation on the deck, wine by the fire, & mineral baths. This solar powered home has easy access to outdoor adventures. Options include Laundry, Wood Stove (fire logs avail $), & fully equipped Kitchen. Whether you're looking for a getaway, family event, road stop, or retreat - you're welcome here. Pets require PRE-APPROVAL.

Guest favourite
A private cabin is nestled alongside the Rogue River, surrounded by lush greenery and mature trees. A spacious deck overlooks the water, providing a serene outdoor space. A pathway leads from the cabin to the river's edge, enhancing accessibility.
Cabin in Trail
4.96 out of 5 average rating, 239 reviews

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.

Guest favourite
A charming cottage exterior features a dark gray facade with white trim and a welcoming orange door. Two evenly spaced windows are flanked by neatly trimmed shrubs, and a concrete pathway leads to the front entrance, surrounded by a well-maintained lawn.
Home in Medford
4.99 out of 5 average rating, 297 reviews

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.

Guest favourite
Home in Trail
4.95 out of 5 average rating, 223 reviews

Eagle’s Nest Cottage | 40 mins to Crater Lake

Rogue River Retreat enjoy a cozy weekend of unplugging and quality time with loved ones! - 60 minutes to Crater Lake National Park - Riverfront retreat on the tranquil Rogue River - Wake up to breathtaking river views - Lounge in the hammock while watching rafters, ducks, and fish drift by - Play Ping-pong - BBQing on the patio - Fishing off the dock (BYO poles) - Cook family meals together - Play board games - Stream movies on the Roku TV

Top Guest favourite
The exterior of the Ivy Cottage is framed by lush greenery and trees. A covered porch with seating is visible, inviting outdoor relaxation. A stone pathway leads up to the home, flanked by decorative rock borders and garden features, offering a charming and welcoming entrance.
Home in Jacksonville
4.97 out of 5 average rating, 314 reviews

Ivy Cottage

Located in the heart of quaint Jacksonville, the Ivy Cottage is a cozy getaway. Just blocks from the main street, a short walk to Britt Music Festival and 8 minute drive to Rogue X makes this the perfect location for all visitors of the area. The Ivy Cottage was built in 1925 and was newly refurbished with love in 2018. Offering 2 bedrooms, 1 bath, and a memory foam sleeper sofa, can sleep up to 6 guests.

Top Guest favourite
Home in Central Point
4.93 out of 5 average rating, 176 reviews

Close to Wineries • Hot Tub • Near Jacksonville

Bright, modern guesthouse in Rogue Valley wine country. This private retreat is perfect for couples or small families. Enjoy serene farmland views, a private hot tub, and a full kitchen. Comfortably sleeps up to 4. Located just minutes from Medford, wineries, and hiking trails, offering a perfect blend of countryside charm and convenient access to local attractions.

Popular amenities for Jackson County holiday rentals

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