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2nd Street Cottages

2nd Street Cottages is located on a quiet side street in the historic and lovely Railroad District. This is the perfect location providing all of the comforts and charm of a historic (renovated) home and the option of not having to drive to experience all that downtown Ashland has to offer. Just two short blocks to theatres, unique shops, world class dining, art galleries, tasting rooms, day spas, entertainment and people watching.

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Abbott's Cottages

Nestled around a central courtyard, Abbott's Cottages offer delightful accomodations ranging from a charming one room studio to a spacious three bedroom house. . .

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Abigail's Bed & Breakfast Inn

Built in 1904, Abigail's offers original Craftsman details, comfortable period-appointed rooms, colorful gardens and a relaxing front porch. Abigail’s is ideally located within walking distance of downtown Ashland; the Oregon Shakespeare Festival theaters; boutique shops, restaurants, Lithia Park and Ashland Creek.

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Ashland Commons - Groups, Families, Hostel

Perfect for individuals, families, small or large groups. Three units w/kitchen, common area, A/C, WiFi, parking, laundry, and patios. Private, family rooms, and dorms. Mtn. views; walk to downtown/OSF. A relaxing, affordable option.

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Ashland Creek Inn

Ashland’s finest all-suite boutique hotel. Luxury suites featuring sitting rooms, private decks, and kitchenettes all overlooking Ashland Creek in a private park setting.

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Ashland Haus

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom.

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Ashland Hills Hotel & Suites

Located on 14 acres the hotel boasts panoramic views of the surrounding mountains, intimate courtyard patio and spacious 2-room suites featuring: in room coffee and tea . . .

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Ashland Springs Hotel

Located in the heart of downtown Ashland, this historic landmark offers 70 tastefully appointed guest rooms with all modern amenities, complimentary breakfast & parking, restaurant, spa & salon. Hotel’s charming banquet spaces are perfect for your wedding, corporate meeting or any social gathering. Offering off site catering!

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Ashland's Main Street Inn

The new owner of Ashland's Main Street Inn intends to continue to offer top-quality travelers accommodations. Two spacious suites with full kitchens provide luxury and comfort in the elegant 1883 Victorian located two blocks from the Plaza.

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Bayberry Inn

A Retreat for All your Senses. This beautiful award-winning, Aesthetic Boutique B&B, is a 1920s Craftsman-style home. Offering all of today’s amenities while maintaining Ashland’s historic charm. Adorned with antiques and One-of-a-Kind works of art. Your accommodations include -beautiful comfortable rooms with private bathrooms, flat screen TVs with streaming services, Wi-Fi throughout, luxury BFF toiletries, USB chargers, ceiling fans, central heat/air, fresh robes, and more.

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Callahan's Siskiyou Lodge

Callahan’s Siskiyou Lodge is a full service lodging and dining resort nestled in a sylvan canyon of Southern Oregon's Siskiyou Mountains just off of Interstate 5! This enchanting high country restaurant and lodge is ten minutes south of Ashland, Oregon and offers 19 spacious hotel rooms with Jacuzzi tubs, wood-burning fireplaces and adjoining terraces.

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Carlisle Garden Suites

Nine luxury cottages and suites surround an exquisite tranquil garden, just a block away from downtown. All our units have been recently updated and have private entrances, kitchenettes with cooktops, refrigerators and basic supplies, luxury baths, free WI-FI and TV, A/C, morning pastries and coffee, and free parking. We have Queen, and King and Twin bed options.

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Chanticleer Inn

Walk to theaters and Ashland’s historic downtown. A warm welcome greets you at the Chanticleer Inn, a top-rated 1920 Craftsman in a quiet neighborhood; surrounded by secluded gardens. Enjoy gourmet breakfasts, organic shade-grown coffee, lots of cookies, AC, free WiFi, all ensuite bathrooms, fragrance-free products, and much more! Some rooms are dog-friendly.

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Country Willows Inn & Estate

Country Willows Inn is a charming boutique Southern Oregon bed and breakfast located in Ashland, Oregon. We’re located on five scenic acres just two miles from downtown Ashland. The grounds at Country Willows Inn perfectly combine the historical country atmosphere with modern amenities. The grounds feature a seasonal heated pool, hiking trails, stunning mountain views, and beautiful gardens with koi ponds and a duck pond.

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Friends of the Oregon Caves & Chateau

We are a non-profit organization cooperating with the National Park Service (NPS), bureau of the United States Department of Interior, in the preservation, stewardship and improvement of cultural and natural resources of the Oregon Caves National Monument. The Oregon Caves and the Chateau are unique assets of national significance that contribute to the identity and economic well-being of the local community.

Green Springs Inn

Green Springs Inn

Green Springs Inn & Cabins offers a sustainable getaway opportunity in a forested setting near the crest of the Southern Cascades. For a generation, Southern Oregonians and visitors from afar have made Green Springs Inn a breakfast, lunch and dinner destination.

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Iris Inn

The Iris Inn has been welcoming guests since 1982. In a peaceful setting, a short stroll from town, guests are invited to enjoy the spacious gardens surrounding the inn.

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Jacksonville Inn

The Jacksonville Inn is a historic bed and breakfast inn, restaurant, and wine shop located in the heart of the National Historic Landmark town of Jacksonville, Oregon.

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Journey To and Fro Travel

Travel Planning and Consulting

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Lake of the Woods

The perfect getaway! This high mountain lake resort sits beside one of the most beautiful and rare natural lakes found in the Southern Oregon Cascades. Amidst majestic firs and lofty pines one can enjoy a variety of outdoor recreational activities... summer & winter! We currently have 26 Cabins and 27 Rv sites. Visit our website at www.lakeofthewoodsresort.com

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Lithia Springs Resort & Wine Garden

Lithia Springs Resort - Relax. Soak. Dream. Stay in Ashland Oregon's only Luxury Hotel with in-room hot springs baths, HDTV, and WiFi.

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McCall House

Just one block from the acclaimed Oregon Shakespeare Festival, our lovingly restored Italianate mansion offers luxurious accommodations in Victorian inspired suites and guestrooms.

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McCracken Property Management

We're a boutique property management company specializing in short term rentals (Airbnbs) in Ashland! With a blend of experience as owners/investors as well as property managers we know what it takes to take care of your baby (property) and make sure our guests do too!

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Oak Street Cottages

Just a block to downtown, Oak Street Cottages are Ashland's very first vacation rental, now 20 years being "Ashland's Favorite Family Inn" Rent one cottage or all four!

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Oregon Wellness Retreat

Oregon Wellness Retreat, located within the Bayberry Inn, offers 3-to-7-night all-inclusive getaways. Everything from a romantic weekend to intensive workshop and connection building weeklong experiences.

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Palm Cottages

Conveniently located across from Southern Oregon University, Palm Cottages offer the opportunity to step outside of the ordinary. Guests enjoy award-winning gardens, mature trees, and lawn seating areas that are as welcoming as they are comfortable. The Oregon Shakespeare Festival is close-by (about 3 mins by car), making The Palm an ideal accommodation for travelers attending the plays as well as for those who desire unique style, complimentary wireless internet, effortless parking, and lush

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Paschal Winery and Vineyard

PASCHAL WINERY AND VINEYARD was started in 1990 by Roy Paschal and reflects the love for his family and for the beautifully-handcrafted artisan wines that bear the Paschal family label. When visiting, be sure and take notice of 5 new acres planted to Tempranillo, Malbec and Cabernet Sauvignon plus expanded Pinot Noir and Syrah plantings...

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Plaza Inn & Suites at Ashland Creek

Nestled in the heart of downtown Ashland you will find the area's premier lodging facility. Plaza Inn & Suites at Ashland Creek. We offer guests a unique experience they won't soon forget! With elegant furnishings and charming atmosphere, the 91 room upscale property will couple small town hospitality with the sophistication and culture Ashland has become world famous for.

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Prospect Historic Hotel-Motel and Dinner House

Crater Lake National Park’s closest full service town is showcased by the nationally registered Prospect Historic Hotel-Motel and Dinner House.

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Silver Frog Guesthouse

Cozy Guesthouse walkable 3 blocks to downtown Ashland shops, dining and entertainment.

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Stay Ashland - Ashland's Bed & Breakfast Network

Ashland’s Bed & Breakfast Network is a free reservation referral service provided by an association of more than 20 inns for visitors to Ashland, Oregon. The ABBN member innkeepers have met the high standards set for membership and demanded by our guests. On our member page, we invite you watch our short video because we love sharing our town with you!

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Swank House

CLASSY VIBES, LOCAL TOUCHES At every Swank House, your comfort is covered. Live it up with delightful touches around every corner — intentional, thoughtful, and locally-rooted in Ashland. 9 locations. Steps to Shakespeare theatre. Your Swank House awaits.

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The Peerless Hotel

Welcome to the historic Peerless Hotel, where comfort and quietude combine in this rare and exceptional historic property. This boutique hotel, which is listed on the National Register of Historic Places, is beautifully situated in an exceptionally quiet neighborhood that is walking distance to the Oregon Shakespeare Festival, Lithia Park, and the shopping and dining destinations of the Ashland Plaza.

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Timbers Inn & Suites

Pick of theatre goers for years! Clean, family-friendly, charming and affordable units. We have offered value in Ashland lodging for 50 years! Free Wi-Fi, continental breakfast, refrigerator, microwave, in-room coffee machines and pool. Walking distance to restaurants, bars and shopping. Across from Southern Oregon University dorms and approximately 1 mile from downtown Ashland and Oregon Shakespeare Festival. Book direct for a discounted rate.

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Tom Smith Travel

A full service travel agent for The Travel Society-A Virtuoso Member.  Air, hotel, cruise, car, tours, adventure travel and foreign independent travel.  Full service agency.

Travel Southern Oregon

Travel Southern Oregon

Travel Southern Oregon is the regional tourism development manager for the southern half of the Oregon. This 36 year old organization covers Douglas, Josephine, Jackson, Klamath and Lake Counties by supporting communities with assistance in tourism economic development

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Weisinger Family Winery

Weisinger's of Ashland is a family owned and operated winery situated on a hill overlooking the Rogue Valley. Founder, John Weisinger, was a pioneer in developing the Rogue Valley as awine producing region. His son, our Winemaker, Eric Weisinger, joins him today. Together their emphasis is on quality and capturing the finest character from the fruit grown in the Rogue Valley Appellation of Southern Oregon.

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Willow Witt Ranch

Nestled nearly a mile high in the Cascades just east of Ashland, 440 acre Willow-Witt Ranch is the hidden jewel of Southern Oregon.

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Winchester Inn

What do you get when you blend history, romance, with comfort, charm and culinary expertise? You get The Winchester Country Inn. On the National Registry of Historical Places, the Inn has been written up in the "Best Places to Kiss" and the rooms have been called " a wonderful fusion of Victorian charm with modern sensibilites."

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