Vacation Rentals in Ashland, OR

This charming cottage is situated in Ashland, just 2km from Weisinger Family Winery, Southern Oregon University, and the Schneider Museum of Art, offering a convenient base for exploring the town. It has received excellent reviews from previous guests.
The property features two bedrooms, two bathrooms, and can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, parking, and free Wi-Fi.

This six-bedroom apartment, sleeping up to twelve guests, is situated in Ashland's Siskiyou-Hargadine Historic District, within a 1.6km walk of the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library.
The 260 square metre property boasts a fully equipped kitchen, Jacuzzi, garden, terrace, parking, and free Wi-Fi; nearby attractions include the Angus Bowmer Theatre and Thomas Theatre, both within 1.6km.

This European-style straw bale home is located on 14 wooded acres in Ashland, just a few kilometres from the town centre and its restaurants, theatres, and shops. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
The two-bedroom home has a spacious open-plan living area with vaulted ceilings and earthen floors, covering 153 square metres. This eco-friendly dwelling offers a unique and sustainable experience with amenities including a fireplace, a terrace, a garden, a spa, parking, and internet access.

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 one-bedroom apartment is located in Ashland, just 5km from Weisinger Family Winery, Southern Oregon University, and Schneider Museum of Art, making it a convenient base for exploring the city's cultural attractions. It has received excellent user ratings, so you can be sure of a comfortable stay.
The 42 square metre apartment comfortably sleeps two guests and has a fully equipped kitchen, a private patio, and a garden. You'll also enjoy the use of a spa, parking, and free 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 charming bungalow is situated in a prime location just a 1.6km walk from the heart of Ashland, placing you within easy reach of the Oregon Shakespeare Festival, Lithia Park, and the Lithia Artisans Market. The property consistently receives excellent ratings for its cleanliness, location, and user experience, making it a popular choice for travellers.
The bungalow comfortably accommodates up to eight guests across three bedrooms and two bathrooms. It boasts a fully equipped kitchen, a spacious living area with a gas fireplace, a large deck with a gas grill, and a level 2 car charger for electric vehicles.

Grandview of Ashland, a one-bedroom house, is situated near Lithia Park and the Oregon Shakespeare Festival, approximately 2.9 kilometres from each.
This self-catering property sleeps up to 11 guests and boasts a fully equipped kitchen, three bathrooms, a Jacuzzi, sauna, private garden, free Wi-Fi, and free private parking; in-unit laundry facilities add further convenience.

This Ashland apartment, situated in the Historic Railroad District, is steps from downtown and within easy walking distance of the Oregon Cabaret Theatre and Allen Elizabethan Theatre.
The 35-square-metre (377 sq ft) self-catering flat offers a king-size bed, private parking, a patio (June-October), and accommodates two guests, with a microwave, air conditioning, and Wi-Fi included; one pet is permitted.

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 charming flat is situated in the heart of Ashland's Historic Downtown District, just 0.16 km from the Oregon Shakespeare Festival. The surrounding area is brimming with restaurants, wineries, and shops, making it a perfect base for exploring the town.
The apartment offers three bedrooms, sleeping up to [number of guests], and spans 110 square metres. Amenities include a kitchenette, a washer/dryer, a smart TV with DVR, and private off-street parking, ensuring a comfortable and convenient stay.

This smoke-free flat is located in the heart of Ashland's historic downtown district, just a kilometre from the Oregon Shakespeare Festival and the Ashland Library. The property has received excellent ratings for location, cleanliness and user experience.
The flat is well-equipped with a kitchen including a fridge, freezer, microwave, dishwasher and a washing machine. Relax in the garden, enjoy a game of tennis or take advantage of the spa and the balcony.

This charming cottage is situated on a working farm just a few kilometres from the centre of Ashland, offering a peaceful escape from the town's hustle and bustle while still being close to its attractions. It enjoys excellent ratings for location, cleanliness and user experience.
The self-catering property can accommodate two guests and provides a private area for relaxation, with a kitchen equipped with a fridge and microwave oven. You can enjoy a farm setting, stunning views, access to nature, and a welcoming atmosphere.

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 Ashland city centre apartment is ideally located less than 0.16km from a grocery store and coffee shop, and within a short walk of restaurants, the Plaza Center, and the Chozu Bath & Tea Gardens.
The 37 square metre flat offers a king-size bed, two bathrooms, and a kitchenette with microwave, accommodating two guests and featuring a private outdoor lounge area, high-speed 5G internet, and access to laundry facilities.

This Ashland apartment, a stone's throw from the Plaza Centre and a short walk (less than 0.8 km) from a grocery store, offers prime downtown accommodation near Ashland's key attractions.
The 28-square-metre flat features two bathrooms, sleeps two guests, includes a kitchenette with microwave, and boasts a private terrace, high-speed 5G internet, and a king-size bed.