Vacation Rentals in Ashland, OR

This Airstream caravan, named 'Peaceful Airstream With Panoramic Views', is located on a 5+ acre estate near Ashland, Oregon, approximately 6.4 km from Ashland's town centre and 21 km from Medford Airport, offering easy access to the Shakespeare Festival and Britt Festivals.
The 6.1-metre-long, fully refurbished Airstream features a queen-size bed, shower, small bathtub, fully equipped kitchen, solar panels, and accommodates up to four guests, with a private terrace and access to the estate's garden.

This farm stay is located just a few kilometres from downtown Ashland, near the Oregon Shakespeare Festival and a range of restaurants, offering a peaceful escape from the city. It has received excellent user ratings, highlighting its high standards.
The farmhouse spans 269 square metres and comfortably accommodates up to 10 guests. It boasts a large in-ground pool, a hot tub, a chef's kitchen, and a variety of recreational activities, including bocce ball, basketball, and a pond with a pergola and swing.

The Mountain House by WanderLodges is located in Ashland, just 2.2 kilometres from the ScienceWorks Museum and 2.9 kilometres from the Oregon Shakespeare Festival, making it a convenient base for exploring the town's attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The three-bedroom house spans 158 square metres and can comfortably accommodate up to six guests. Amenities include a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, air conditioning, and private parking, ensuring a comfortable and enjoyable stay.

This five-bedroom Ashland farmhouse, sleeping fourteen, is situated on a mountainside, approximately 5 kilometres from Weisinger Family Winery and Emigrant Lake, and within 10 kilometres of the ScienceWorks Hands-On Museum and North Mountain Park.
The 418-square-metre property boasts a fully equipped kitchen with dishwasher, air conditioning, a jacuzzi, a terrace, a garden, parking, an arcade/game room, barbecue grills, and a hot tub; ideal for families seeking a relaxing getaway.

This Ashland carriage house apartment is situated within a gated castle community near Interstate 5, offering easy access to Ashland's city centre and is only a short drive from local attractions.
The one-bedroom, one-bathroom apartment sleeps four guests and boasts access to a sunroom, library, coffee bar, and patio within the main chateau, plus on-site amenities including vineyards, gardens, and a pond.

This one-bedroom cottage is situated in Ashland's Skidmore Historic District, just 0.6 kilometres from the town centre.
The property features a private garden, a fully equipped kitchen, and laundry facilities, making it ideal for a comfortable stay for up to three guests.

This townhouse, ideal for family stays, is located just a few blocks from Ashland's central district, offering easy access to dining, entertainment, Lithia Park, and the Oregon Shakespeare Festival.
Enjoy spectacular mountain views from the covered deck and garden of this fully furnished, 3-bedroom, 2-bathroom property, which sleeps up to six guests and is available for monthly rentals of 30 days or more.

This modern three-bedroom, three-bathroom house in Ashland, Oregon, is situated in a quiet residential neighbourhood at the foot of the mountains, a short walk (approximately 1.5km) or cycle ride from the town centre and directly adjacent to mountain trails.
The property boasts a spacious open-plan layout, sleeping up to seven guests, and features a gourmet kitchen, a Jacuzzi, a fitness centre with exercise bike and treadmill, extensive outdoor amenities including a hot tub, ping pong table, trampoline, and a large garden backing onto a wooded park and seasonal creek.

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 holiday cottage in Ashland offers a prime location, a mere 5-minute stroll from the Oregon Shakespeare Festival and 400 metres from the Oregon Cabaret Theatre, placing it conveniently 1 block from downtown Ashland.
Guests can enjoy air-conditioned rooms with complimentary private parking and WiFi, featuring a terrace, private bathroom, and flat-screen TV, with no bachelor(ette) or similar parties permitted.

Château Herbe, near I-5 and Ashland, Oregon's city centre, offers a unique stay minutes from Grizzly Peak and Weisinger Family wineries.
This one-bedroom castle apartment, sleeping two, features a private en-suite bathroom, queen-sized bed, and access to shared chateau facilities including a sunroom, library, coffee bar, and patio, alongside on-site gardens, orchards, and a pond.

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 one-bedroom cottage in Ashland offers excellent walkability, situated just metres from downtown attractions, the Oregon Shakespeare Festival, and Lithia Park, with convenient access to local trails.
This rental property accommodates up to four guests and features a king-size bed, a fully equipped kitchen with a fridge, freezer, and microwave, air conditioning, in-unit laundry, and a private, fenced patio, with parking and internet also provided.

This four-bedroom apartment is located just 0.2 kilometres from Ashland's bustling town centre, putting you within easy walking distance of shops, restaurants, Lithia Park and the Oregon Shakespeare Festival. It has received excellent ratings for location, cleanliness and user experience.
The apartment is spacious and comfortable, sleeping up to eight guests, and features a fully equipped kitchen, air conditioning, parking and internet access. You can also enjoy the beautiful woodwork and leaded glass details of this historic Craftsman property, as well as explore the nearby Lithia Park and its walking trails, gardens and picturesque creek.

This studio flat in Ashland offers an excellent location, situated directly adjacent to the 93-acre Lithia Park and just a 5-minute walk from downtown's dining, shopping, and the Oregon Shakespeare Festival, with easy access to the Allen Elizabethan Theatre and Angus Bowmer Theatre.
This self-contained accommodation for two guests features independent heating and cooling, radiant floor heating, a fully equipped kitchen with a coffee maker and ice maker, and shared laundry facilities, making it ideal for exploring the cultural attractions of Ashland.

This mountain-situated flat in Ashland offers a 7-minute drive to Lithia Park and a 5-minute drive to North Mountain Park, with cultural venues like the Thomas Theatre and Oregon Shakespeare Festival a mere 6-minute drive away.
This 148 square metre dwelling accommodates up to six guests across three bedrooms and two bathrooms, providing essential amenities such as complimentary Wi-Fi, air conditioning, a dryer, and an ironing board, alongside easy access to local wineries and outdoor pursuits like hiking and biking.