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The Red Tail Inn is a restored farmhouse located in downtown Ashland, just a short walk from the Oregon Shakespeare Festival and the city's charming shops and restaurants. This historic inn offers a unique blend of old-world charm and modern amenities, making it a perfect choice for travelers seeking a comfortable and convenient stay.
The Red Tail Inn features three separate suites that can accommodate up to 12 guests, ideal for families or groups of friends. Each suite includes a full kitchen, a luxurious bathroom, and comfortable beds with high-quality linens, ensuring a relaxing and enjoyable stay. Guests can also enjoy the shared hot tub, garden, and pet-friendly accommodations.

The Mountain House by WanderLodges is located in Ashland, just a short walk from the ScienceWorks Museum, the Oregon Shakespeare Festival, and the Schneider Museum of Art. This vacation rental has received excellent ratings for location, cleanliness, and overall user experience.
The house has 3 bedrooms and 2 bathrooms, offering space for up to 6 guests. The fully equipped kitchen, air conditioning, free Wi-Fi, and private parking make this a comfortable and convenient place to stay.

This Queen Anne-style house is located in Ashland, Oregon, less than a mile from downtown, providing easy access to shops, theaters, and restaurants.
The 5,380-square-foot home features two bedrooms, one bathroom, and can comfortably accommodate four guests, offering a fully equipped kitchen with gas stove, a fenced yard, three off-street parking spots, and a 55-inch smart TV.

This charming cottage is located in Ashland, just a short distance from Weisinger Family Winery, Southern Oregon University, and the Schneider Museum of Art. It's a great option for travelers looking for a comfortable and convenient base to explore the city. Guest rave about the cottage's excellent rating, making it a popular choice for visitors.
The cottage offers two bedrooms and two bathrooms, comfortably sleeping up to six guests. It's equipped with a range of amenities, including a kitchen, a swimming pool, a spa, and a terrace for relaxing and enjoying the beautiful Ashland weather.

This downtown Ashland apartment rental is one block from a grocery store and coffee shop, two blocks from an escape room, and within walking distance of the Oregon Shakespeare Festival and Lithia Park.
This 300-square-foot unit features one bedroom, two bathrooms, a king-size bed, a kitchenette with a microwave and mini-refrigerator, a private outdoor lounge, high-speed 5G internet, and accommodates two guests.

The Barclay Klum House by WanderLodges is located in Ashland, a short walk from the Oregon Shakespeare Festival and close to the Schneider Museum of Art. This 1,500 square foot apartment features two bedrooms, one bathroom, and can accommodate up to seven guests, making it ideal for families or groups visiting the area.

This house in Ashland is located one block from downtown, a 5-minute walk to the Oregon Shakespeare Festival, and 400 yards from the Oregon Cabaret Theatre, with the Ashland Library 7 minutes away on foot and Lithia Park 0.4 miles distant.
This accommodation offers air conditioning, complimentary WiFi, a terrace, and free private parking, with no bachelor(ette) or similar parties permitted.

This modern apartment is located in Ashland's Historic Downtown District, just a short walk from Paschal Winery and StoneRiver Vineyards, putting you right in the middle of all the action. The apartment is spacious, with 1180 square feet of living space, including three bedrooms and two bathrooms. The apartment offers a fully equipped kitchen, a smart TV with DVR, a washer/dryer, and a jetted tub in the upstairs bathroom, along with a choice of balconies and patios for relaxing.

This charming house is located in Ashland's Historic Railroad District, just a short walk from the Ashland Library and the Oregon Shakespeare Festival. Guests consistently rate it excellent, making it a popular choice for travelers.
The 2-bedroom house comfortably accommodates up to 6 guests in its 870 square feet of space. Enjoy amenities like a fully equipped kitchen, outdoor patio with barbecue, and a private spa, perfect for a relaxing getaway.

The Redtail Inn - 3 Suites Sleeps 12 is located in downtown Ashland, just steps from the Ashland Library and a short walk from the Oregon Cabaret Theatre. The inn has received excellent ratings for its location, cleanliness, and overall experience.
The inn offers three suites that can sleep up to 12 guests, making it ideal for families or groups of friends. Guests have access to amenities like free Wi-Fi, private parking, a terrace, air conditioning, and a TV.

This smoke-free apartment is located in Ashland's Historic Downtown District, just a short walk from the Oregon Shakespeare Festival, the Oregon Cabaret Theatre, and the Allen Elizabethan Theatre. Guests have rated this property excellent for location, cleanliness, and overall experience.
This rental features a fully equipped kitchen, a comfortable living area with a Smart TV, and a peaceful garden for relaxing. Enjoy convenient amenities like a washing machine, a coffee/tea maker, and access to a spa, tennis court, and parking.

This Ashland vacation rental is conveniently located near Lithia Park and the Oregon Shakespeare Festival, with easy access to Grizzly Peak and Weisinger Family wineries.
The two-bedroom, three-bathroom home sleeps six guests and boasts a gourmet kitchen with a wine fridge, a jacuzzi, sauna, and a private terrace with valley views, plus nearby access to hiking, mountain biking, and the RRRink.

This Ashland apartment rental offers a centrally located one-bedroom, one-bathroom unit perfect for solo travelers, providing easy access to Ashland's attractions.
The 1-bedroom apartment includes a kitchen with a refrigerator, air conditioning, a swimming pool, a jacuzzi, a garden, and a fitness center, accommodating one guest and offering a comfortable stay.

This farm stay is located just a short drive from downtown Ashland, the Oregon Shakespeare Festival, and award-winning restaurants, offering breathtaking views of Mt. Ashland and the Rogue Valley. The property has earned excellent user ratings for its peaceful atmosphere and stunning scenery.
This four-bedroom, three-bathroom farmhouse spans 2,900 square feet and comfortably accommodates up to ten guests. Enjoy the in-ground pool, hot tub, fire pit, and outdoor games like bocce ball, basketball, and ping pong, as well as the chef's kitchen, formal dining room, and the unique master suite with a 2,000 lb basalt bathtub.

This Ashland carriage house apartment is located in a gated community near Interstate 5, minutes from downtown Ashland and offering breathtaking mountain views.
The one-bedroom, one-bathroom unit sleeps four, includes a full kitchen, and provides access to a shared sunroom, library, coffee bar, patio, and on-site amenities such as vineyards, gardens, orchards, and a pond with pergola and fountain.

This Ashland Chateau Herbe apartment, near I-5 and downtown, offers stunning views of the Rogue Valley and mountains.
The one-bedroom, one-bathroom unit sleeps four, features a full kitchen, private balcony, and access to shared chateau amenities including a sunroom, library, and coffee bar, plus on-site gardens and vineyard exploration.