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Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

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The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

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Kelly’s Farm 4 miles to Ashland

Nestled on the border of the Shakespeare hamlet of Ashland, Oregon, is Kelly’s farm. Only four miles away, come soak in the views. Kelly’s farm has horses, goats, chickens, gardens, fruit and nut trees with views of Mt. Ashland’s seven-thousand feet high profile in its front and bucolic rolling hills in its back. Bring your dog! You have access to a large fenced in yard right from your private entrance and deck. ***Unfortunately we are not set up for children under 4 or kitty cats. ***

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Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

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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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Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. Charging is available for your electric cars in the upper parking area.

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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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Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

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Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin has remodeled upgrades and is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakepeare Fetival, Plaza shops, beautiful Lithia Park and Resturants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the pituresque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings!

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Weisinger Winery Vineyard Cottage

Our vineyard cottage is located at Weisinger Family Winery in Ashland, Oregon. Built c. 1920, our vineyard cottage was the original farmhouse on the property and was recently remodeled in order to encompass the amenities and comforts of home. The hot tub and BBQ on the deck overlook our Pinot Noir vineyard. The property has wonderful views and privacy. A complimentary bottle of wine, cheese, and crackers are awaiting your arrival along with a free tasting in our tasting room.

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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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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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Mountain House property studio apartment

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Siskiyou Chateau

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Mountain Retreat CozyCabin Hyatt Prairie w/HOT TUB

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The Birdhouse Retreat| Views

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Tiny Groove with sauna and soaking tubs

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Historic Dunn Ranch Ashland Or.

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Perk's home away from home

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Timberlake Pines Suite

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