Vacation Rentals in Ashland, OR

This Medford property, a spacious four-bedroom house, is situated 19 kilometres north of Ashland and 11 kilometres south of Jacksonville, offering easy access to the Oregon Shakespeare Festival and Britt Festival.
The 251-square-metre dwelling boasts a jacuzzi, terrace, garden, and parking, accommodating eight guests with amenities including a fully equipped kitchen, Wi-Fi, and access to nearby attractions such as the Beekman House and Craterian Ginger Rogers Theatre.

This Queen Anne-style apartment in Ashland, Oregon, is located less than 1.6 km from Ashland's downtown area, offering easy access to shops, theatres, and parks.
The property, sleeping four guests, boasts a well-equipped kitchen with a European gas stove and electric convection oven, two bedrooms (one queen, one double), a bathroom with a soaking tub and walk-in shower, private off-street parking, and a fenced yard.

Meadowsweet Farm, a substantial dwelling in Talent, is situated 9.9 kilometres from the Oregon Shakespeare Festival and 10.1 kilometres from Lithia Park, with the ScienceWorks Museum and Schneider Museum of Art also 12.4 kilometres away.
This air-conditioned property spans 297 square metres, accommodates up to 18 guests across its three bathrooms, and features an outdoor kitchen, WiFi, and private parking, making it suitable for larger groups seeking a holiday let.

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.

Hanna's House, a centrally located dwelling in Ashland's historic district, is a short walk from the Oregon Shakespeare Festival, the Oregon Cabaret Theatre, and Ashland Public Library.
This 165-square-metre (1776 sq ft) property features one bedroom, one bathroom, and sleeps four guests, offering a full kitchen, private garden, spa, parking, and air conditioning.

This Ashland cottage, situated in the Skidmore Academy Historic District, offers easy access to Grizzly Peak and Weisinger Family Wineries (within a short driving distance, depending on the precise location within the district).
The one-bedroom property sleeps four, featuring a queen bed, sofa bed, and queen air mattress, a fully equipped kitchen with microwave and dishwasher, plus WiFi, air conditioning, and streaming services (HBO, Hulu, Netflix, Disney+).

This Queen Anne-style holiday home in Ashland, Oregon, is situated less than 1.6km from the downtown area, offering easy access to shops, theatres, and restaurants.
The 500 square metre property boasts two bedrooms, one bathroom with a luxurious soaking tub and walk-in shower, a full kitchen including a gas stove and grill, three off-street parking spaces, a fully fenced garden, and can comfortably accommodate four guests.

This French Country style villa is located on the outskirts of Ashland, offering a peaceful retreat on three acres of land while still being just a short distance from the town's restaurants, shops, and attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The villa is a single-storey property with a floor area of 186 square metres. Amenities include a fully equipped kitchen, a Jacuzzi, a terrace, a garden, a spa, parking, and a rec room with a sofa bed, ensuring a comfortable and enjoyable stay for guests.

This modern apartment is situated in Ashland's Historic Downtown District, just a short walk from the ScienceWorks Hands-On Museum and The RRRink. The area is bustling with activity, offering a vibrant mix of shops, restaurants, and cultural attractions.
This two-storey property spans 110 square metres and comfortably sleeps up to 8 guests with three bedrooms and two bathrooms. It features a fully equipped kitchen, a smart TV with DVR, a washer/dryer, a jetted tub, a balcony, and a patio.

This Ashland holiday home is ideally located in the Historic Railroad District, less than 0.8km from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Angus Bowmer Theatre.
The 149 square metre property boasts two bedrooms, three bathrooms, and accommodates four guests, offering a fully equipped kitchen, garden, balcony, and parking.

This Ashland Railroad District apartment, located a short walk from a grocery store, coffee shop, and escape room, offers easy access to downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens.
The 37 square metre flat comprises two bedrooms, one bathroom, and sleeps two guests, featuring a king-size bed, jetted tub, private veranda with workspace, a kitchenette with microwave and mini-refrigerator, high-speed 5G internet, and a 65" Smart TV with Netflix.

This house is located in Ashland's Historic Downtown District, just 0.5km from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The 3-bedroom house spans 118 square metres and features a fully equipped kitchen, two bathrooms, a washing machine, and a garden. Guests can enjoy amenities such as air conditioning, parking, and a spa, making it ideal for a comfortable and relaxing stay.

This comfortable apartment is ideally located in the centre of Ashland, just a short walk from the Oregon Shakespeare Festival theatres. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. It comes equipped with a kitchen, air conditioning, parking, and internet access, making it a convenient and comfortable base for exploring Ashland.

This apartment is located in the heart of Downtown Ashland, just a short walk from the main street and all the city's attractions. It has received excellent ratings for location, cleanliness and overall user experience.
The flat is ideal for couples and comes with a comfortable king-size bed and a modern kitchen. It also features a private parking space, a seasonal patio, and is pet-friendly with a small fee for one pet.

This detached house in Ashland offers a prime location for Oregon Shakespeare Festival attendees, situated a mere 6-minute walk from Ashland Library and 0.8 kilometres from the Oregon Cabaret Theatre, with Southern Oregon University also within a 15-minute walk.
This spacious 186 square metre residence accommodates up to 15 guests with one bedroom and two bathrooms, featuring air conditioning, a private terrace, a garden, a spa, and a fully equipped kitchen including a dishwasher and oven, with Wi-Fi and nearby skiing opportunities.

The Oak Street Studio is situated on Water Street, just a few hundred metres from Lithia Park and the renowned theatres, making it a convenient base for exploring Ashland's cultural heart. The studio has received excellent ratings for its location, cleanliness, and overall user experience.
This self-catering apartment comfortably accommodates four guests with a king-size bed in the bedroom and a queen-size pull-out sofa in the living area. The studio includes parking, Wi-Fi, a TV, a kitchenette with a microwave and a full-size fridge, and a work-friendly space with a desk and a dining table.