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Modern Airy Retreat - Views, Walk to Everything

Enjoy the perfect mix of walkable Ashland and your private, airy, urban hideaway. Set in the historic Railroad District with fabulous cafes, restaurants and shops in the same block and nearby, this modern studio over a detached garage has views of trees or mountains from every window. It's only a 5 minute walk to Downtown and a 10 minute walk to Lithia Park and the Oregon Shakespeare Festival. Should you wish, you could park your car in your dedicated space and not use it again during your stay.

The Cutie Little Loft

The Cutie Little Loft is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with brand new appliances, and extra special little touches, will make your stay easy and enjoyable. Whether your main destination is Medford, or perhaps you plan to visit nearby cities like historic Jacksonville or Ashland, the CLL is a great point of access for all. Numerous restaurants, hiking trails and wineries are nearby allowing an eventful trip to the beautiful Southern Oregon.

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!

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.

Studio Cottage near downtown Ashland - Queen Bed!

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

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.

Mindy’s Ashland Hideaway

Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

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 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.

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. NOTE: AFTER JULY 1ST, 2026, COYOTE MOON WILL NO LONGER BE AVAILABLE FOR BOOKING AS AN AIRBNB.

Sweet Breeze Bungalow

Charming Alley bungalow in the historic railroad district. Walk score of 93. Immerse yourself in the heart of Ashland. 5 min. walk to downtown, an easy 8 min. walk to Shakespeare & Cabaret Theaters. Walk to pubs, restaurants, coffee shops, spa's, markets, movie theater, Lithia Park, Japanese garden and trailheads all within 5-12 mins. Nice bike ride to wineries 15 min away, or a 30 min. drive to Mt. Ashland for skiing, hiking, biking and more adventures.

Clean and Cozy Historic Home near Ashland

Bedroom 1 is set up with a full size bed, with all-cotton sheets. Mattress is medium firm. Bedroom 2 has a daybed with soft mattress. Bathroom is a few steps away. Ventilating windows, ceiling fan and individual mini-split with a/c or heat in bedroom. Radiant heat and ceiling fan in living room. Easy walk to restaurants, parks, library, bus line, groceries. I live nearby so am available if needed but you will have the house all to yourself!

Ashland tiny home with view and barrel sauna

Vaulted 8.5x20 craftsman tiny home built in 2023. Large wrap around deck overlooking the hills of Ashland. Stunning space to reset, relax and enjoy. Five minutes to downtown ashland. Great bird watching. Fall asleep to the sound of crickets on a comfortable queen bed in the upstairs loft. BBQ out on the deck, with all new amenities. Mini split heat pump and shared barrel sauna. We hope you enjoy the space as much as we do.