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Applegate Wine Country cottage!

Our "Lil Wanderer" cottage is located right in the middle of Southern Oregon wine country. You will be staying in a cottage on a vineyard with our own winery and tasting room onsite. We’re open Saturday & Sunday. Also, with 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport,Troon, Schmidt, Blossom Barn, Rosellas & Solaro just to name a few. Downtown Grants Pass & Jacksonville are 30 minutes away. Highway 5 is 30 min away

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Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

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Mt Ashland Log Cabin w/Swedish sauna by PCTrail

Beautiful hand built rustic log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is the perfect quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

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The Red Dragon House

Just a few minutes outside of Ashland, this unique and spacious property will put you in a rural setting with excellent views of the surrounding hills of the Rogue Valley. Located on 5.2 acres, with two security gates that are, remnants of a previous cannabis operation, the property affords ample privacy, and is invisible from the street, providing a perfect getaway for those that seek it. We are adjacent to I-5, so if road noise is an issue, this property may not be right for you.

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C Street Station Cottage

Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

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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.

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Modern Crash Pad | Pet Friendly | West Wing

NEW! Upgraded to KING bed!! A modern suite located steps away from the Ashland conference center and just minutes to downtown. Step into this light filled space which boasts stunning walk in shower, antique brass fixtures, and convenience kitchenette. Thoughtfully designed including heated bathroom tiles. Enjoy the breathtaking views of Grizzly Peak, and the local non-commercial airport. 1 pet welcome with fee. Note that we do not have a fenced yard. (#18-243).

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Cozy camping close to town

The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, hot water kettle, lending library, and games; this adorable camper is supremely functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland's picturesque downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

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Manzanita Cottage

Enjoy staying in this newly-constructed cottage in the heart of Ashland's historic railroad district. Park your car and enjoy all that Ashland has to offer by foot. Easy walking distance to downtown shops and restaurants, OSF, Lithia Park and the Ashland Food Coop. Outdoor enthusiasts can start their mountain biking, running or hiking adventures right from their door. Your hosts can help to point you in the right direction. (Permit #: PA-2018-00531)

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Rogue River Retreat

A nature lovers retreat on the beautiful Rogue River. Watch osprey from the sprawling cedar deck, fish for salmon right on the river bank, or take a soak in the deep tub, this peaceful cabin you won't want to leave. Located half way between Grants pass and Medford with easy access to the 5 freeway, you can enjoy all that Southern Oregon has to offer. The cabin has one deluxe bathroom and one cozy bedroom that has a king size bed with a water view.

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Coyote Moon

Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.8 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island. Perfect for a romantic couples getaway and also great for those visiting Ashland for the Oregon Shakespeare Festival. Wireless internet and Netflix and internet TV.

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The Barn at Emigrant Creek

You will be a 10 minute drive from Downtown Ashland and feel like you are out in the country. The home sits on 8 private acres and has river frontage and a beach on the year round Emigrant Creek. There are beautiful views in all directions of mountains, trees and wildlife. The home is a two story residential barn built in 2012 and remodeled in 2022 (the main living quarters is upstairs).

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seo.landing_pages.refinements.washer-and-dryer.APARTMENT

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Broken Chair Ranch

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Great location to I-5 and city! King bed!

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Downtown 3 Bedroom Upstairs Flat with views "B"

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Suite Madrona

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Light and Bright! Entire 2 Bedroom Apt!

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Brand New Stylish MCM Studio

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Cowslip's Lower Garden Suite

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Boho-Modern |Lux Spa |Close to Downtown

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Charming Cottage, Walk To Downtown!

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Ivy Cottage

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Clean, pet friendly, 2-Bedroom Cottage with yard.

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Hygge Hideaway. A home for rest and adventure

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Private Carriage House

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Southern Oregon Gem (EV Charger)

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Cheerful new 2 bedroom home in cul de sac Netflix

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Perfect Location! Entire house, pet friendly!

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Black Pearl

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Modern, retro updated bungalow

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The Executive Suite

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Plaza North Suite 203 Windsor

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Spacious Modern Condo Walk Downtown & OSF

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Plaza North Penthouse

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Spacious Modern Condo Walk To Downtown & OSF

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Plaza North Suite 201 Alexander

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