Find short term rentals in Ashland, OR at the best prices
188 available short term rental offers
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Best Short term and Weekly rentals in Ashland, OR
9.9 480 reviews
Ashland, OR
05/09 – 07/09
$272/nighttotal: $544 (2 )
Charming Well Appointed Cottage In Ashland ( 800 + Sq. Ft. )
1 2
cottage , Ashland
This charming cottage is situated in the mountains near Ashland, within easy reach of ScienceWorks Hands-On Museum, North Mountain Park, and Lithia Park, offering a peaceful escape from the city. The property has received excellent ratings for cleanliness, location, and overall experience. The cottage offers a comfortable living space for up to two guests, with one bedroom and one bathroom. It comes equipped with a kitchen, a garden, and a range of modern amenities, including Wi-Fi and a Smart TV, as well as access to ski-in/ski-out facilities for winter sports enthusiasts.
9.9 144 reviews
Ashland, OR
08/08 – 10/08
$698/nighttotal: $1396 (2 )
Helman Street Penthouse With A View
1 4
apartment , Ashland
This two-bedroom apartment is located in Ashland's Historic Railroad District, just 0.4 km from the Plaza and within walking distance of the Oregon Shakespeare Festival. The apartment boasts a spacious open-plan living area with hardwood floors, a fully equipped kitchen with marble countertops and top-notch appliances, a large private deck with views, and a dedicated office space, making it ideal for families or groups of up to four guests.
9.8 9 reviews
Ashland, OR
17/09 – 23/09
$479/nighttotal: $2874 (6 )
Refurbished Barn On Acerage Just Outside Ashland
1 2
apartment , Ashland
This refurbished barn, offering a country escape on six acres, is located just 7 minutes by car from downtown Ashland and 10 minutes from Lithia Park and the Oregon Shakespeare Festival. This three-bedroom, one-and-a-half bathroom dwelling accommodates six guests and features a jacuzzi, garden, and parking, with opportunities for hiking, wine tasting, and day trips to Crater Lake.
9.8 61 reviews
Ashland, OR
08/08 – 10/08
$1025/nighttotal: $2050 (2 )
Mountain Ave House By Wanderlodges
1 4
apartment , Ashland
This three-bedroom house, situated in suburban Ashland, Oregon, is conveniently located 0.8 kilometres from Ashland's downtown plaza, offering easy access to restaurants, the Oregon Shakespeare Festival, and Lithia Park. The 3-bedroom property boasts a spacious layout with king-sized beds in each bedroom, accommodating up to six guests, and includes a well-equipped kitchen, two bathrooms, a private garden, parking for two cars, and access to a SMART TV.
9.4 200 reviews
Ashland, OR
05/09 – 07/09
$335/nighttotal: $670 (2 )
The Dogwood Suite At Tudor House Vacation Rentals
1 2
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.
9.6 37 reviews
Ashland, OR
17/09 – 23/09
$220/nighttotal: $1320 (6 )
1853 Farmhouse-country Yet Five Minutes To Ashland
1 2
house , Ashland
This 1853 farmhouse guesthouse is situated near Ashland's Wellsprings, a few kilometres from Lithia Park and the Oregon Shakespeare Festival. The property, offering a queen-size bed plus a loft space (at extra cost), sleeps four and includes a mini-sink, electric kettle, mini-fridge, and a full-size shower/bath; nearby attractions include extensive bike trails.
Ashland, OR
20/06 – 27/06
$349/nighttotal: $2443 (7 )
Ashland Retreat | Tennis. Pool.
1 2
B&B , Ashland
Ashland Hills Hotel & Suites offers a king-size bed guesthouse near downtown Ashland, Oregon, minutes from the Oregon Cabaret Theatre and Lithia Park. This pet-friendly hotel boasts a swimming pool, hot tub, fitness centre, and on-site restaurant, catering to couples with its one-bedroom, one-bathroom layout and capacity for two guests, plus access to various activities including bike rentals and live music.
9.4 8 reviews
Ashland, OR
08/08 – 10/08
$561/nighttotal: $1122 (2 )
Charming 1 Br Orliena Suite In Historic Downtown Ashland, Or. Walk To The Oregon Shakespeare Festival, Shops, And Dining. Features A Kitchenette, Plush Queen Bed, And Shared Hot Tub Access. Dog Friendly!
1 4
apartment , Ashland
This Ashland apartment, situated in the Siskiyou-Hargadine Historic District, is less than 0.8 km from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Ashland Library. The 56 square metre property features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, Jacuzzi, patio, free Wi-Fi, and parking.
9.7 12 reviews
Ashland, OR
08/08 – 10/08
$326/nighttotal: $652 (2 )
Chateau Herbe ~ Rosalind Carriage House 1bdr Apt
1 4
apartment , Ashland
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.
9.6 89 reviews
Ashland, OR
08/08 – 10/08
$702/nighttotal: $1404 (2 )
Blossom View Cottages - Charming Home Near Osf Plaza And Downtown
2 4
apartment , Ashland
This charming house is located in Ashland's Historic Railroad District, just a kilometre from both the Ashland Library and the Oregon Shakespeare Festival. The house has received excellent user ratings, making it a popular choice for travellers. This two-bedroom property spans 81 square metres and can accommodate up to six guests. The house features a fully equipped kitchen, a private garden, a terrace, a spa, and parking.
9.3 343 reviews
Ashland, OR
05/09 – 07/09
$294/nighttotal: $588 (2 )
Arden Forest Inn
1 2
B&B , Ashland
Arden Forest Inn is situated in Ashland, close to Southern Oregon University and around 8 miles from Mt. Ashland Ski Area. This guesthouse consistently receives excellent ratings for its location, cleanliness, and overall experience. The inn features a range of amenities for a comfortable stay, including a swimming pool, a terrace, and a garden. Guests can also enjoy a restaurant, a bar, and a fitness centre, along with room service and free parking.
9.8 14 reviews
Ashland, OR
05/09 – 07/09
$2156/nighttotal: $4312 (2 )
Redtail Inn - 3 Suites Sleeps Up To 12
4 2
house , Ashland
Redtail Inn - 3 Suites Sleeps 12 is located in a quiet neighbourhood in central Ashland, just a short walk from the Ashland Library and a 5-minute drive from Lithia Park. It has received excellent ratings for its location, cleanliness, and overall experience. The inn offers 3 suites, sleeping up to 12 guests, making it ideal for families or groups of friends. Guests can enjoy free Wi-Fi, parking, a terrace, and air conditioning, as well as easy access to the Oregon Shakespeare Festival, Southern Oregon University, and ScienceWorks Museum.
Best family friendly Ashland, OR Short term rentals
Among the 188 accommodations in Ashland, OR, here are the 4 best family friendly rentals
10 5 reviews
Ashland, OR
17/09 – 23/09
$788/nighttotal: $4728 (6 )
Barclay Klum House | Walk To Downtown | Soaking Tub & Gourmet Kitchen
2 2
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 43 reviews
Ashland, OR
17/09 – 23/09
$519/nighttotal: $3114 (6 )
Ashland's Mountain View Vacation Rental.
2 2
cottage , Ashland
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.
9.9 169 reviews
Ashland, OR
02/07 – 06/07
$574/nighttotal: $2296 (4 )
Serenity-themed, Fastest Wifi, 2 King Beds Home
1 5
apartment , Medford
This house is located in the Rogue Valley, just under 6.5km from Medford city centre, close to wineries and the Rogue Valley Country Club. The property has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The 2-bedroom house offers 137 square metres of space and can accommodate up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a Jacuzzi, a terrace, a garden, and parking.
10 36 reviews
Ashland, OR
20/06 – 23/06
$785/nighttotal: $2355 (3 )
"Enchantment" Jacksonville, Oregon
4 5
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 lodging with a kitchen
8.8 3 reviews
Ashland, OR
05/09 – 07/09
$530/nighttotal: $1060 (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.
10 4 reviews
Ashland, OR
20/06 – 23/06
$1115/nighttotal: $3345 (3 )
The R & R
4 5
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.
10 1 review
Ashland, OR
25/06 – 26/06
$563/nightfor 1 night
Step Into Modern Comfort Inside This Beautifully Renovated 2 Bedroom / 1.5 Bath Home. Enjoy A Spacious Chefs Kitchen, Cozy Living Room With Fireplace, And Spa-style Bathroom With Jetted Tub. Close To Downtown Medford And Room For The Whole Family.
3 3
apartment , Medford
This apartment is located in Medford's Downtown district, 400 metres from Cinemark Tinseltown Medford 15 and 1.3 kilometres from the Craterian Ginger Rogers Theatre. This 111 square metre flat sleeps six guests and features three bedrooms, two bathrooms, a private terrace, a fenced garden with a barbecue, complimentary Wi-Fi, air conditioning, a fireplace and a fully equipped kitchen.
9.8 11 reviews
Ashland, OR
25/06 – 26/06
$524/nightfor 1 night
Escape To This Artsy 2-bedroom Mcm Guesthouse In Charming Phoenix, Or. Unwind In The Luxurious Spa Soaking Tub After Exploring Southern Oregon. Features High-end Design For A Stylish, Quiet Retreat.
2 3
apartment , Phoenix
This charming bed and breakfast is situated in Phoenix, Oregon, just 5 kilometres south of Medford and 11 kilometres north of Ashland, making it a convenient base for exploring the region. It has received excellent guest reviews, highlighting its peaceful and comfortable atmosphere. The property offers two bedrooms and one bathroom, spread over 93 square metres and comfortably accommodating up to four guests. It features a private fenced yard, a well-equipped kitchen, a relaxing outdoor space with a hammock, and amenities such as air conditioning, a fireplace, and parking.
Frequently Asked Questions about short term rentals in Ashland, OR
What are the best short term rentals in Ashland, OR?
Cozy Santa Feinspired 2br Retreat With Queen Beds, Sofa Sleeper, Soaking Tub, Fireplace, And Large Fenced Backyard. Great Location Near Medford, Jacksonville Wineries, And Ashland.
3 5
apartment , Medford
This Santa Fe-style flat in Medford offers a central location, placing you 800 metres from the Craterian Theater at The Collier Center, 8 kilometres from Historic Jacksonville, and 19 kilometres from the Oregon Shakespeare Festival in Ashland. This three-bedroom, one-bathroom dwelling spans 89 square metres, accommodates up to six guests, and features a fully stocked kitchen, a lounge with a fireplace, and a secure garden, with parking and Wi-Fi provided.
10 7 reviews
Ashland, OR
05/09 – 07/09
$553/nighttotal: $1106 (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.
9.8 6 reviews
Ashland, OR
17/09 – 23/09
$425/nighttotal: $2550 (6 )
Swank Suites | King With Lux Tub
1 2
apartment , Ashland
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.
Ashland, OR
05/09 – 07/09
$511/nighttotal: $1022 (2 )
Swank Suites | King With Lux Tub
1 2
apartment , Ashland
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.
This three-bedroom house, sleeping six, is situated in Ashland's Historic Railroad District, within 1.6km of the Ashland Library, Oregon Cabaret Theatre, Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre. The property offers free Wi-Fi, a fully equipped kitchen with fridge, microwave, and dishwasher, a garden, parking, and is within easy walking distance of various attractions, making it ideal for families or groups visiting Ashland.
9.5 72 reviews
Ashland, OR
26/06 – 28/06
$159/nighttotal: $318 (2 )
Old Farmhouse
1 2
apartment , Phoenix
This countryside flat, offering a peaceful retreat from Phoenix, is situated just 3.2 kilometres from the nearest motorway, providing convenient access for exploring the region. This one-bedroom, one-bathroom flat accommodates two guests and includes essential amenities such as air conditioning, Wi-Fi, and a kitchen equipped with a fridge, microwave, and dishwasher, alongside on-site parking.
Ashland, OR
26/06 – 28/06
$797/nighttotal: $1594 (2 )
Ashland King Studio W/gym & Pool
1 2
B&B , Ashland
This guest house in Ashland is located near the Rogue Valley, a short drive from the town centre, offering convenient access to the Oregon Shakespeare Festival (approximately 1.5 kilometres away) and Southern Oregon University (approximately 500 metres away). The accommodation provides a private suite for two guests, featuring a king-size bed, air conditioning, Wi-Fi, a swimming pool, a hot tub, a fitness centre, and complimentary on-site parking, with a daily cooked breakfast available for an extra charge.
Ashland, OR
05/09 – 07/09
$1674/nighttotal: $3348 (2 )
Savage Upon Siskiyou | Prime Osf Location
3 2
apartment , Ashland
This Victorian flat is located in central Ashland, a mere 300 metres from the Oregon Shakespeare Festival and downtown attractions. This 3-bedroom, 2-bathroom residence accommodates up to 8 guests and includes a fully equipped kitchen, private parking with an EV charger, and a garden.