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.
Ashland, OR
18/09 – 20/09
337 €/nighttotal: 674 € (2 )
Swank Suites- Top Floor + Private Patio
1 2
apartment , Ashland
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.
10 9 reviews
Ashland, OR
18/09 – 20/09
295 €/nighttotal: 590 € (2 )
Peaceful 1-bedroom Bungalow With Ac In Charming Ashland
1 2
apartment , Ashland
This one-bedroom flat is located just 100 metres north of Ashland's downtown plaza, offering convenient walking access to the Oregon Shakespeare Festival, Oregon Cabaret Theatre, shops, restaurants, Lithia Park, and the Japanese Garden. The 46 square metre bungalow accommodates two guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a private patio and garden, and is ideal for those interested in mountain climbing, hiking, and mountain biking.
10 7 reviews
Ashland, OR
18/09 – 20/09
431 €/nighttotal: 862 € (2 )
Delightful 2~bedroom, Pet~friendly Cottage~walking Distance To Everything!
2 2
cottage , Ashland
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.
9.6 353 reviews
Ashland, OR
25/08 – 26/08
240 €/nightfor 1 night
Oak Street Studio
1 3
apartment , Ashland
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.
10 1 review
Ashland, OR
04/08 – 06/08
199 €/nighttotal: 398 € (2 )
Whimsy On B | The Studio
1 2
apartment , Ashland
This studio apartment is situated just a short walk from downtown Ashland and the Oregon Shakespeare Festival, placing you at the centre of the town's cultural hub. This accommodation offers space for two guests and features a king-size bed, a kitchenette with a toaster oven and hot plate, a full bathroom, and access to a quiet courtyard, all within a private triplex setting.
10 4 reviews
Ashland, OR
18/09 – 20/09
631 €/nighttotal: 1262 € (2 )
Grandview Of Ashland
1 2
house , Ashland
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.
10 26 reviews
Ashland, OR
10/07 – 12/07
311 €/nighttotal: 622 € (2 )
The Ashland Social | Guest Studio
1 2
studio , Ashland
This studio apartment is located just 0.4 kilometres from Ashland Plaza, placing you within easy reach of the city's main attractions, restaurants, and shops. It has received excellent user ratings, making it a popular choice for travellers. The apartment has a private entrance and can comfortably accommodate two guests. It features a kitchenette with a fridge, microwave, and other appliances, as well as Wi-Fi, heating, and parking.
10 19 reviews
Ashland, OR
26/08 – 27/08
333 €/nightfor 1 night
Stroll Inn~central Locale!
1 3
apartment , Ashland
This two-bedroom cottage is located in Ashland's historic Siskiyou-Hargadine District, a short walk from Lithia Park and the town's theatres and restaurants. The self-catering property sleeps four, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and a charming front porch; nearby attractions include spas and yoga studios.
10 92 reviews
Ashland, OR
20/08 – 22/08
169 €/nighttotal: 338 € (2 )
Beautiful Guest Suite With Private Deck Overlooking Forest And Waterfall
1 2
apartment , Ashland
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.
9.6 14 reviews
Ashland, OR
04/08 – 06/08
152 €/nighttotal: 304 € (2 )
Chateau Herbe ~ Vienna Room
1 2
castle , Ashland
Château Herbe, near Interstate 5 and Ashland, Oregon, offers a luxurious stay minutes from downtown Ashland and Grizzly Peak Winery. This French-style château provides a spacious, en-suite room with private patio, sleeping two guests, and access to communal sunroom, library, and coffee bar, plus stunning grounds including vineyards and gardens.
10 66 reviews
Ashland, OR
26/08 – 27/08
502 €/nightfor 1 night
Historic Ohana House - Walk To Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
3 3
apartment , Ashland
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.
Best family friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals
9.7 43 reviews
Ashland, OR
20/08 – 22/08
465 €/nighttotal: 930 € (2 )
Centrally Located Downtown Historic Home W/parking
1 2
apartment , Ashland
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.
9.6 4 reviews
Ashland, OR
07/10 – 12/10
1120 €/nighttotal: 5600 € (5 )
Luxury Ashland Mountain Escape: Pool, Hot Tub
4 4
house , Ashland
This waterfront villa near Ashland, Oregon, is located 1.4 kilometres from Weisinger Family Winery and 4.8 kilometres from Southern Oregon University. The 353-square-metre property boasts four bedrooms, four bathrooms, and sleeps twelve guests, offering a private pool, hot tub, barbecue grills, and a fully equipped kitchen including a dishwasher; laundry facilities are also provided.
Ashland, OR
20/08 – 22/08
625 €/nighttotal: 1250 € (2 )
Savage Upon Siskiyou | Prime Osf Location
3 2
house , Ashland
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.
10 36 reviews
Ashland, OR
27/06 – 04/07
382 €/nighttotal: 2674 € (7 )
"Enchantment" Medford, Oregon
4 2
apartment , Medford
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.
Best Ashland, OR holiday rentals with parking
10 8 reviews
Ashland, OR
04/08 – 06/08
298 €/nighttotal: 596 € (2 )
Barclay Klum House By Wanderlodges
1 2
house , Ashland
This comfortable house is located just 1.5 kilometres from Ashland Library and the Oregon Shakespeare Festival, making it ideal for exploring the town's cultural attractions. The surrounding area is peaceful and quiet, perfect for a relaxing getaway. The property features a fully equipped kitchen, a spacious garden and a terrace, allowing guests to enjoy both indoor and outdoor living. The house also offers a range of amenities, including free Wi-Fi, parking and a Jacuzzi for ultimate relaxation.
Ashland, OR
18/09 – 20/09
362 €/nighttotal: 724 € (2 )
Hanna's House By Wanderlodges
1 2
house , Ashland
This cottage is located 1 kilometre from Ashland's city centre, offering easy access to the Ashland Library, Oregon Cabaret Theatre, and Lithia Park. This property accommodates two guests and features a kitchen with a dishwasher, air conditioning, a garden, an on-site restaurant, and parking, with Wi-Fi provided and laundry services available.
Ashland, OR
04/08 – 06/08
232 €/nighttotal: 464 € (2 )
Whimsy On B | The Studio
1 2
studio , Ashland
This studio apartment is situated in central Ashland, a short walk from the Oregon Shakespeare Festival and the Allen Elizabethan Theatre, and within 2 kilometres of Grizzly Peak Winery and Weisinger Family Winery. The accommodation sleeps two guests and offers a king-size bed, a kitchenette with a toaster oven and hot plate, a private bathroom with a shower, air conditioning, Wi-Fi, and access to a garden and spa, with parking available.
9.4 3 reviews
Ashland, OR
04/08 – 06/08
564 €/nighttotal: 1128 € (2 )
2br Ashland Retreat: Steps To Shakespeare
2 2
apartment , Ashland
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.
Frequently asked questions about holiday rentals in Ashland, OR
What are some interesting places to visit in or near Ashland, OR?
Ashland is a great place to visit! You can't miss the Oregon Shakespeare Festival, which runs throughout the summer. If you're a nature lover, head to the Lithia Park, which has lots of hiking trails and beautiful scenery. For a more active day, try the Ashland Hills Golf Course or take a scenic drive to the Rogue River.
What are the best Airbnb and holiday rentals in Ashland, OR?
Which walking or cycling routes are the best in Ashland, OR?
For a relaxing walk, try the Lithia Park Loop Trail. It's a 2.5km paved path that goes around the park. If you're looking for a more challenging bike ride, head to the Bear Creek Greenway. It's a 16km paved trail that goes through the forest and along the creek.
What sports or outdoor activites can visitors enjoy in and around Ashland, OR?
Ashland is a great place to enjoy the outdoors. You can hike, bike, or even go rock climbing in the surrounding mountains. In the summer, there's great fishing in the Rogue River. If you're feeling adventurous, try whitewater rafting or kayaking.
What are the best holiday rentals with a pool in Ashland, OR?
What other towns or cities can be easily accessed from Ashland, OR?
Ashland is a great base for exploring Southern Oregon. You can easily drive to Medford, which is about 20 minutes away. It's a larger city with more shops and restaurants. Further afield, you can visit the Crater Lake National Park, which is about a 2-hour drive away.
What are the best rentals for families and kids in Ashland, OR?
What amenities are commonly available in vacation rentals in Ashland, OR?
Vacation rentals in Ashland typically have all the amenities you need for a comfortable stay. You can expect to find a fully equipped kitchen, a comfortable living space, and bedrooms with comfortable beds. Many rentals also have laundry facilities, a patio or balcony, and Wi-Fi.
What are the best rentals or Airbnbs with a jacuzzi in Ashland, OR?
What time of year is best to rent a vacation rental Ashland, OR?
The best time to visit Ashland depends on what you're looking for. The summer is the busiest time, with the Oregon Shakespeare Festival in full swing. If you prefer cooler weather and fewer crowds, consider visiting in the spring or autumn.
What are the local dishes in Ashland, OR region?
The local cuisine in the Ashland area features fresh, seasonal ingredients. Try a local favourite, the Rogue River trout, which is often served with a side of roasted vegetables. You can also find delicious burgers, pizzas, and other comfort food at local restaurants.
Destinations nearby
Best Ashland, OR holiday rentals with a balcony
9.4 11 reviews
Ashland, OR
18/09 – 20/09
409 €/nighttotal: 818 € (2 )
Barclay Klum House By Wanderlodges
2 2
apartment , Ashland
This two-bedroom apartment is located in Ashland, Oregon, just a short walk from the Oregon Shakespeare Festival and close to other attractions such as the Schneider Museum of Art and Lithia Park. The 139 square metre property features a fully equipped kitchen, a private balcony with garden views, and parking for guests, making it ideal for families or groups of up to seven people.
8.5 2 reviews
Ashland, OR
04/08 – 06/08
501 €/nighttotal: 1002 € (2 )
Pioneer Vacation Rentals - Pioneer Craftsman House
3 2
house , Ashland
This Craftsman-style holiday home is situated in Ashland, Oregon, a short walk (less than 1.6km) from Lithia Park and within a couple of miles (approximately 3.2km) of Southern Oregon University, the ScienceWorks Museum, and the Schneider Museum of Art. The 167 square metre property boasts three bedrooms, two bathrooms, and sleeps eight, featuring a fully equipped kitchen, private parking, a terrace, and garden; guests can enjoy nearby attractions such as the Oregon Shakespeare Festival and Oregon Cabaret Theatre.
Ashland, OR
18/09 – 20/09
789 €/nighttotal: 1578 € (2 )
Whimsy On B- 1 Block To Downtown Ashland
2 2
house , Ashland
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.
Ashland, OR
07/10 – 12/10
492 €/nighttotal: 2460 € (5 )
Lithia Springs Resort
2 4
resort , Ashland
Lithia Springs Resort is located in Ashland, Oregon, 4 kilometres from the city centre, offering convenient access to Ashland's attractions. This hotel boasts a spa, indoor and outdoor swimming pools, a fitness centre, and various business facilities including a conference hall, alongside a bar, library, and picnic area, ensuring a comfortable stay.
Best pet friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best pet friendly rentals
8.8 3 reviews
Ashland, OR
20/08 – 22/08
238 €/nighttotal: 476 € (2 )
Swank Suites | Step Free King
1 2
apartment , Ashland
This first-floor apartment in Ashland's historic Railroad District is situated one block from a grocery store and coffee shop, two blocks from an escape room, and within easy walking distance of downtown restaurants, Ashland Plaza Center, and Chozu Bath & Tea Gardens. The 37-square-metre (approximately 398 square feet) flat offers a king-size bed, a kitchenette, a private outdoor lounge, shared laundry facilities, high-speed 5G internet, a 65-inch smart TV with Netflix, and accommodates two guests; parking is also available.
9.5 84 reviews
Ashland, OR
10/07 – 12/07
257 €/nighttotal: 514 € (2 )
Studio With King-size Bed
1 2
studio , Ashland
This studio apartment is located in Ashland, just under 1.6km from the Oregon Shakespeare Festival and a little over 1.6km from ScienceWorks Museum, making it an ideal base for exploring the town's cultural attractions. The property has received excellent ratings for its location, cleanliness and overall user experience. The apartment offers one bedroom and one bathroom, comfortably accommodating up to two guests. Amenities include free Wi-Fi, private parking, a king-size bed, a flat-screen TV, and a kitchen equipped with a fridge, freezer, and microwave.
9.8 10 reviews
Ashland, OR
25/08 – 26/08
222 €/nightfor 1 night
Charming Carriage House In Ashland Near Downtown
1 3
cottage , Ashland
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+).
10 16 reviews
Ashland, OR
20/08 – 22/08
206 €/nighttotal: 412 € (2 )
Peaceful, Spacious Home On 8 Acres. Pet-friendly, Close To Town, And A Creek!
2 2
apartment , Ashland
This two-bedroom apartment is situated in a rural setting just 8 kilometres from downtown Ashland, offering a peaceful retreat amidst the natural beauty of the surrounding countryside. The apartment has received excellent user ratings, highlighting its appeal for those seeking a tranquil escape. The apartment, which can accommodate up to six guests, features a spacious living area with high ceilings and ample natural light. The property offers a range of amenities including a private jacuzzi, a terrace, a garden, and a spa, along with parking facilities and access to the internet.