Find short term rentals in Ashland, OR at the best prices

This Ashland, Oregon house, built in 1887, is centrally located, within walking distance of Ashland's downtown area and a short distance (less than 1.6km) from Lithia Park.
Sleeping six guests across three bedrooms and one bathroom, this property offers a well-equipped kitchen, air conditioning, parking, internet access, and pet-friendly facilities.

This Talent guesthouse enjoys a convenient location near Interstate 5, opposite a park and cycle path.
The single-level, self-catering unit offers a bedroom, bathroom, and private dining areas (both indoor and outdoor), sleeping up to two guests, and features a small refrigerator, microwave, and coffee station.

This Ashland family home, a 148 square metre property, is situated a short 2.4 kilometre walk from Lithia Park and within easy reach of the Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre, plus the Oregon Shakespeare Festival (all within a 2.4 kilometre radius).
The three-bedroom dwelling boasts two bathrooms, sleeps eight guests, offers a fully equipped kitchen (including fridge, microwave, and dishwasher), a jacuzzi, patio, garden, parking, and free Wi-Fi.

The Red Tail Inn is a charming farmhouse guesthouse located in downtown Ashland, just a short walk from the Oregon Shakespeare Festival theatres and the town's shops, restaurants, and coffeehouses. It's a convenient base for exploring the vibrant cultural scene of this historic town.
The inn offers three separate suites, each with its own bathroom and kitchenette, accommodating up to 12 guests. Guests can enjoy luxurious amenities such as double walk-in rain showers, granite countertops, and a shared hot tub, perfect for relaxing after a day of exploring.

This charming house is located in the Siskiyou-Hargadine Historic District, just 1.5 kilometres from Southern Oregon University and the Oregon Shakespeare Festival. It has consistently received excellent ratings for location, cleanliness, and overall experience.
This one-bedroom property offers 93 square metres of space and can comfortably accommodate five guests. The house features a fully equipped kitchen, a fireplace, a washing machine, a terrace, a garden, and parking, making it ideal for a comfortable and enjoyable stay in Ashland.

This two-bedroom, two-bathroom house in Ashland is situated 500 metres from the Oregon Shakespeare Festival, shops, and restaurants.
This property offers accommodation for up to five guests with internet, air conditioning, and a kitchen, perfect for those visiting Southern Oregon.

This Medford apartment, ideally located for exploring the city and its surroundings, is within 3.2km of Lithia & Driveway Fields and 1.6km of Fichtner-Mainwaring Park.
This one-bedroom, one-bathroom flat offers 59 square metres of space, sleeping up to five guests and is close to Rogue Valley Mall and The RRRink.

This Ashland holiday home is located in the Historic Railroad District, a short 4.5km drive from the Oregon Cabaret Theatre and within walking distance of the Ashland Library.
The two-bedroom, two-bathroom property sleeps four guests and offers amenities including Wi-Fi, a fully equipped kitchen with dishwasher, in-unit laundry, and air conditioning; nearby attractions include North Mountain Park and the ScienceWorks Hands-On Museum.

This restored farmhouse, situated in Medford, is a mere 700 metres from Paschal Winery and StoneRiver Vineyards, offering a distinctive wine country escape with easy access to downtown Medford's attractions.
This family-friendly property accommodates up to 18 guests across 7 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a garden with an outdoor kitchen and fireplace, and parking, making it ideal for large groups seeking a comfortable stay.

This Ashland countryside cottage, located 5-8 minutes (approximately 3-5km) from Ashland's downtown area and the Oregon Shakespeare Festival, offers easy access to local wineries.
Sleeping eight guests, this four-bedroom, two-bathroom property boasts a large fenced backyard with a dog kennel, a grape arbor seating area, and a fully equipped kitchen including a dishwasher, plus air conditioning and Wi-Fi.

This luxurious Ashland apartment, close to Lithia Park and the Oregon Shakespeare Festival, offers easy access to wineries such as Grizzly Peak and Weisinger Family, and is within a few kilometres of hiking and mountain biking trails.
The two-bedroom property, sleeping up to six guests with a pull-out sofa bed and boasting three bathrooms, features a gourmet kitchen with wine fridge, hot tub, sauna, outdoor fire pit, and a terrace with sweeping valley views; a 20% discount on Oregon Shakespeare Festival B and C section tickets is also included.

This two-unit property is situated in Ashland's downtown district, a 5-minute walk from the Oregon Shakespeare Festival and 2 blocks from the central downtown area.
This accommodation offers a 3-bedroom apartment and a separate studio, sleeping up to six guests, with a private courtyard, a porch, and amenities including a full kitchen, kitchenette, fridge, freezer, microwave oven, dishwasher, and air conditioning.

The Ashland Carter House B&B is located in the historic downtown district of Ashland, within easy walking distance of the Ashland Shakespeare Festival and other attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
The Billiard Room is a private, self-contained unit within the main house, suitable for two guests. It features a kitchenette, a comfortable queen-sized bed, a private bathroom, and access to the garden, patio, and swimming pool during the summer months.

This Ashland apartment, situated in the Siskiyou-Hargadine Historic District, is less than 0.8 km from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library.
The 56 square metre property features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, Jacuzzi, patio, free Wi-Fi, and parking.

This guest house is situated in Ashland's Siskiyou-Hargadine Historic District, just 366 meters from the Oregon Shakespeare Festival and close to the Oregon Cabaret Theatre.
This 335 square meter accommodation offers a dog-friendly 'Rosette' room for two guests, featuring garden access, air conditioning, internet, and a terrace, with gourmet breakfasts and free parking provided, all within reach of skiing and Weisinger Family Winery.

This charming guesthouse is located in Ashland's Historic Downtown District, just a short walk from Lithia Park and Thomas Theatre, with the Oregon Shakespeare Festival and Oregon Cabaret Theatre a 10-minute walk away. The B&B has consistently received excellent ratings for its location, cleanliness, and overall experience.
The guest house features a shared space with a coffee/tea station, a microwave, and a refrigerator, perfect for a quick bite or a relaxing break. Guests can enjoy a complimentary full breakfast each morning, along with free Wi-Fi, self-parking, and a manager's reception, making it a great base for exploring Ashland's attractions.