This two-bedroom, one-bathroom house in Ashland, Oregon is conveniently located approximately 1.6km from Ashland Dog Park and within 4.8km of North Mountain Park, Lithia Park, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre. The smoke-free property sleeps four guests and offers amenities including a sauna, hot tub, in-house laundry facilities, and is within easy reach of Ashland's major parks and theatres.
9.5 60 reviews
Ashland, OR
09/09 – 13/09
128 €/nighttotal: 512 € (4 )
Loft On The Lane
1 1
apartment , Ashland
This Ashland studio apartment is situated in the historic Skidmore district, 0.4 kilometres from Ashland Plaza and within easy walking distance of parks. The self-contained apartment, sleeping two guests, boasts a queen-size bed, fully equipped kitchenette with convection oven, private deck with Grizzly Peak views, high-speed Wi-Fi, air conditioning, and designated off-street parking.
10 23 reviews
Ashland, OR
09/09 – 13/09
248 €/nighttotal: 992 € (4 )
Cowslip Historic Main House, Great For Gatherings!
1 1
apartment , Ashland
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.
10 7 reviews
Ashland, OR
04/08 – 06/08
227 €/nighttotal: 454 € (2 )
Swank House -Downtown Suite- Pet Friendly
1 2
apartment , Ashland
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.
9.9 239 reviews
Ashland, OR
15/10 – 19/10
206 €/nighttotal: 824 € (4 )
Historic Cottage Close To Plaza
1 1
house , Ashland
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.
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.
9.8 76 reviews
Ashland, OR
20/08 – 22/08
370 €/nighttotal: 740 € (2 )
Pet Friendly W/ Hot Tub By Town!
1 2
apartment , Ashland
This three-bedroom apartment is situated in a residential area, just a short walk from the centre of Ashland, Lithia Park and the Varsity Theatre. The property consistently receives excellent ratings for its location, cleanliness and overall experience. The apartment comfortably accommodates up to six guests and features a well-equipped kitchen, a large garden and a private deck with a barbecue. Guests can enjoy the vintage stereo system, the bar, and the family-friendly games provided.
9.4 16 reviews
Ashland, OR
20/08 – 22/08
177 €/nighttotal: 354 € (2 )
Chateau Herbe ~ Oberon Suite W/ Kitchen
1 2
apartment , Ashland
This Ashland apartment, a mile (1.6km) from Ashland Dog Park and within three miles (4.8km) of Lithia Park, North Mountain Park, the Allen Elizabethan Theatre, and the Angus Bowmer Theatre, offers stunning mountainside views. The one-bedroom, one-bathroom flat sleeps four, boasting a fully equipped kitchen, private balcony, shared garden, Smart TV, and parking; nearby activities include exploring Ashland's renowned parks and theatres.
10 37 reviews
Ashland, OR
26/08 – 27/08
300 €/nightfor 1 night
Hanna's House | Downtown Retreat, Steps To Osf
1 3
bungalow , Ashland
Hanna's House, a self-contained apartment, is situated just 0.16 km from Ashland's town centre, offering easy access to shops, restaurants, and Lithia Park. This one-bedroom cottage sleeps four guests, boasting a full kitchen with dishwasher, air conditioning, heated floors, private parking, and garage storage for outdoor equipment.
10 4 reviews
Ashland, OR
07/10 – 12/10
651 €/nighttotal: 3255 € (5 )
The R & R
4 4
apartment , Talent
This holiday home is situated in Southern Oregon, a 5-minute drive from downtown Ashland, offering convenient access to multiple lakes, hiking trails, and local wineries. This expansive 743 square meter property boasts four bedrooms, two bathrooms, and capacity for ten guests, featuring a heated swimming pool, a gourmet kitchen with a six-burner gas range and two ovens, a formal dining room, and ample parking for an RV.
9.7 319 reviews
Ashland, OR
15/10 – 19/10
211 €/nighttotal: 844 € (4 )
The Maple Apartment At Tudor House Vacation Rentals
2 1
apartment , Ashland
This apartment is located in the Siskiyou-Hargadine Historic District, just under 2 kilometres from Southern Oregon University and the Oregon Shakespeare Festival. The area is charming and steeped in history, offering a unique and authentic Ashland experience. Guests have consistently rated the apartment as excellent for its location, cleanliness, and overall experience. The apartment offers two bedrooms and two bathrooms, providing ample space for up to six guests within its 84 square metre floor area. It includes a well-equipped kitchen, a terrace, a garden, a spa, and parking, along with internet access, a DVD player, and books, ensuring a comfortable and enjoyable stay.
9.7 55 reviews
Ashland, OR
25/08 – 26/08
427 €/nightfor 1 night
Oak Tower Cottage
2 3
apartment , Ashland
This charming cottage is situated on Oak Street, just a short walk from the vibrant downtown area of Ashland, which is home to theatres, restaurants and art galleries. The property has consistently received excellent ratings for location, cleanliness and overall guest experience. The cottage has two bedrooms and two bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, air conditioning, parking, internet access and a private entrance.
Best family friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best family friendly rentals
10 12 reviews
Ashland, OR
15/10 – 19/10
722 €/nighttotal: 2888 € (4 )
The Ashland Social | Entire Estate
4 1
apartment , Ashland
This five-bedroom Ashland house, sleeping up to twelve guests, is conveniently located less than 1.2km from Southern Oregon University and the Schneider Museum of Art, and under 2km from North Mountain Park and the Oregon Cabaret Theatre. The 282-square-metre property boasts five bathrooms, a private swimming pool, Jacuzzi, sauna, terrace, garden, and fully equipped kitchen; free Wi-Fi and parking are also included.
10 5 reviews
Ashland, OR
09/09 – 13/09
498 €/nighttotal: 1992 € (4 )
Barclay Klum House | Walk To Downtown | Soaking Tub & Gourmet Kitchen
2 1
apartment , Ashland
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.
9.8 151 reviews
Ashland, OR
15/10 – 19/10
213 €/nighttotal: 852 € (4 )
Beautiful And Peaceful Cottage Close To Downtown
1 1
apartment , Ashland
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.
10 8 reviews
Ashland, OR
15/10 – 19/10
334 €/nighttotal: 1336 € (4 )
Barclay Klum House By Wanderlodges
1 1
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.
Best Ashland, OR holiday rentals with parking
9.5 32 reviews
Ashland, OR
20/08 – 22/08
387 €/nighttotal: 774 € (2 )
Stroll Into Ashland From Abigail's Two Bedroom Private Vacation Cottage.
1 2
cottage , Ashland
Abigail's Self Catering Cottage in Ashland, Oregon, is conveniently located within walking distance of the Ashland Theatres, the Plaza, and Lithia Park. This 65 square metre (700 square foot) self-catering holiday home sleeps four guests in two bedrooms, boasting a fully equipped kitchen, a spa, a garden, parking, and free Wi-Fi.
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.
9.4 3 reviews
Ashland, OR
04/08 – 06/08
208 €/nighttotal: 416 € (2 )
Swank Suites + Private Porch Patio
1 2
apartment , Ashland
This Premier Suite, situated in Ashland's Historic Railroad District, is a one-minute walk from a grocery store and coffee shop, two minutes from an escape room, and within easy walking distance of downtown restaurants, the Plaza Centre, and Chozu Bath & Tea Gardens. This 37-square-metre (approximately 398 square feet) first-floor apartment features a king-size bed, a jetted tub, a kitchenette with microwave and mini-refrigerator, private outdoor lounge access, high-speed 5G internet, and accommodates two guests.
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.
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
10 5 reviews
Ashland, OR
18/09 – 20/09
791 €/nighttotal: 1582 € (2 )
Hot Tub | Sauna |Firepit |Sleeps 6!
2 2
apartment , Ashland
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.
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.
9.4 201 reviews
Ashland, OR
15/10 – 19/10
184 €/nighttotal: 736 € (4 )
The Dogwood Suite At Tudor House Vacation Rentals
1 1
apartment , Ashland
This apartment is situated in the Siskiyou-Hargadine Historic District, just 1.5 kilometres from Southern Oregon University, Ashland Library, and the Oregon Cabaret Theatre, and less than 1.6 kilometres from the Oregon Shakespeare Festival and Thomas Theatre. It has consistently received excellent ratings for location, cleanliness, and overall user experience. This one-bedroom, two-bathroom flat spans 74 square metres and comfortably accommodates up to five guests. Enjoy a fully equipped kitchen, a terrace, a garden, a spa, parking, and free Wi-Fi in public areas, along with a washing machine, a TV and DVD player, and air conditioning.
Ashland, OR
26/08 – 27/08
493 €/nightfor 1 night
Whimsy On B- 1 Block To Downtown Ashland
2 3
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.
Best pet friendly Ashland, OR holiday rentals
Among the 203 accommodations in Ashland, OR, here are the 4 best pet friendly rentals
9.4 3 reviews
Ashland, OR
07/10 – 12/10
1210 €/nighttotal: 6050 € (5 )
Ashland Group Retreat! The Redtail Inn Offers 3 Full Suites Within One Booking, Sleeping Up To 12. Great Location For The Shakespeare Festival. Ample Space For Your Large Family Or Friend Group.
4 4
apartment , Ashland
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.
9.6 355 reviews
Ashland, OR
26/08 – 27/08
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.
Ashland, OR
07/10 – 12/10
687 €/nighttotal: 3435 € (5 )
Meadowsweet Farm- Sleeps 18, Outdoor Kitchen
7 4
house , Talent
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.
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.