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Holiday houses in Jackson County

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Top-rated holiday rentals in Jackson County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright living room features large windows that allow abundant natural light, complemented by a comfortable brown sofa and a cozy armchair. Lush green plants add a touch of nature, while a simple coffee table rests atop a textured area rug.
Home in Jacksonville
4.99 out of 5 average rating, 322 reviews

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, fireplaced open living room with an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, Britt Gardens, and more

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 cozy living area features wooden paneled walls and a stylish electric fireplace. Comfortable seating is provided by a plush sofa and a large ottoman. A decorative rug lies on the wooden floor, and natural light filters through the window covered with horizontal blinds.
Cabin in Grants Pass
4.92 out of 5 average rating, 316 reviews

Charming 2br cabin 300ft from the Rogue River.

Located next to the beautiful Rogue River, minutes from interstate 5, between Medford and Grants Pass. The Carley Cabin is your place to create memories of a lifetime, whether you are fishing(one of the best fishing holes), rafting, wine tasting (local wineries galore), going to Britt or Shakespeare, exploring Crater Lake or historic Jacksonville, taking a Hellgate Jet Boat excursion or just a getaway. Come barbeque and relax on the patio or take a walk down to the river and enjoy the fire pit.

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.

Guest favourite
Guesthouse in Jacksonville
4.94 out of 5 average rating, 145 reviews

La Petite Maison + Hot Tub

Welcome to La Petite Maison! Come take it easy at our unique and tranquil home away from home. Located in the heart of the Applegate with nearby wineries and exquisite views of the mountains. Our guest house is equipped with 1 master bedroom, full kitchen/bath, dining and living room with and private SPA on your very own deck! Only a 10 minute drive from the historic town of Jacksonville. At La Petite Maison you will have the peace and quiet of the country, and all that you may need.

Top Guest favourite
A comfortable living area features a grey sofa with orange accent pillows and a light purple armchair. A decorative area rug in rich colors anchors the space. Large windows allow for natural light, complemented by vibrant orange curtains and a wall-mounted TV.
Apartment in Phoenix
4.95 out of 5 average rating, 186 reviews

5 Star Luxury Southern Oregon Suite

Great little getaway on the outskirts of town. Away from the hustle and bustle of the city center, but minutes away from all the great places the Rogue Valley has to offer. This 800 sq foot apartment has been completely renovated to meet all the needs of travelers that are looking for an overnight stay or a long term place to land. This space offers updated heating and air, strong wi-fi, separate bedroom and working space. 2 smart TV's, designated parking, and a private entrance.

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.

Top 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

Popular amenities for Jackson County holiday rentals

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  2. United States
  3. Oregon
  4. Jackson County