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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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Secluded Forest Log House 15 minutes to Ashland

Beautiful hand built rustic log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to downtown Ashland, 20 minutes to Mt. Ashland Ski Area, and a five minute walk to Pacific Crest Trail. This home is the perfect quiet, serene getaway: close enough to Ashland to be convenient, yet completely secluded and private. Features include private covered parking, fully equipped kitchen, large private covered deck overlooking the forest, seasonal wood-fired sauna, and walking trails.

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Comfortable 2 bedroom guesthome with cottage charm

Keep it simple at this peaceful and centrally-located place. This recently completed guesthouse provides the perfect getaway and retreat to see beautiful Southern Oregon. Located within the heart of Central Point, this large lot gives you the feel of being out on the farm. With fruit trees, hens and a beehive you will enjoy the beauty of simple living. Located conveniently off of interstate 5 this can be a quick stay but also a central location to explore all that Southern Oregon has to offer.

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Tiny Cottage w/Firepit/Hottub/Outdoor tubs

Enjoy the charm of staying in a Tiny Forest Cottage, surrounded by nature on the outskirts of town. This tiny cottage has all the essentials that you need for your stay. Tucked between Grants Pass & Merlin (8 mins from Merlin & 15mins from Grants Pass). The closest access to the river is only 10 mins away at Matson Park! After a day of exploring; stargaze in your cabins outdoor bath-tubs, enjoy the peaceful wooded view from the hot tub or roast smores by the fire pit. Perfect Couples getaway!

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The Loft at Highcrest

The Loft at Highcrest is a wonderful hideaway to relax and unwind with all the amenities of home. We've taken extra care in creating a versatile space filled with natural light that includes two outdoor areas to lounge in. Guests will have full use of laundry facilities, wi-fi and a complete kitchen. At 1,000 sqft there's plenty of room to stretch out. The Loft is situated just minutes from wineries, amazing restaurants and shopping. This is a pet and smoke free loft and property.

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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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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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Wood Hamlet - Picasso Cottage by Downtown, kitchen

Our 'Picasso Cottage' sleeps up to 2 adults and is perfect for those who wish to enjoy artful living close to downtown Ashland! The space is the entire bottom floor of Carriage House, with full bathroom, bedroom (queen bed) with sitting area, washer/dryer, living room and full kitchen. Between shows relax on patio or by the swimming pond in garden. Private parking behind Carriage House. Walk to theater! (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

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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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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, French press, hot water kettle, lending library, and games; this adorable camper is both functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

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BEE WELL Organic Spa Garden Studio

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

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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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Boho-Modern | Lux Spa | Close to Downtown

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Peace on the Rogue river Studio

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Suite Madrona

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West Park Unit B

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Light and Bright! Entire 2 Bedroom Apt!

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Peaceful Secluded Getaway in the forest

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Broken Chair Ranch

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

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Casa Bella

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Ashland Haus Retreat - 1 block from downtown!

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Britt Bungalow in the Heart of Jacksonville

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Peaceful Private Retreat on Rogue River Downtown

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Hygge Hideaway. A home for rest and adventure

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Mid Century Modern 2 Bedroom, Walk to Downtown

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Private Carriage House

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The Downtown Mint

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The Executive Suite

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Peaceful, quiet, pet-friendly home with a king bed

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Selah House!

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Mahar Homes - Plaza North 203 Windsor Suite

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Phoenix OR Duplex-Full House Rental (1,100 Sq Ft)

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Spacious Modern Condo Walk To Downtown & OSF

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Modern, retro updated bungalow

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Black Pearl

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