Downtown Ashland Rentals

Home to world-class theater, summer and winter outdoor adventure, shopping, dining, and more. Our properties allow easy access to the cultural, culinary, and relaxing experiences that make Ashland the crown jewel of the Rogue Valley.


Properties Available 32 properties available
Aloha House is a 2 bedroom, 2 bathroom open floor plan, modern luxury home that sleeps 4. The property is made up of two studios with separate kitchen, living, bathing, and sleeping areas connected by a spacious and beautifully designed outdoor patio. Both have king-sized beds and bathrooms, one with a spa tub and sauna and the other with a shower.
Hot Tub Hot Tub
Hot Tub
Hot Tub & Seasonal Pool
Aloha House
2 Bedrooms
$174 - $1,214 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
The Anne Hathaway House has seven bedrooms and seven and a half bathrooms, a huge commercial kitchen, dining room with seating for 12, a living room with a library, washer and dryer, front porch and ample outdoor seating surrounded by garden. Downstairs there are three king bedrooms, and one queen bedroom, each with its own bathroom. There is a sit
Kitchen & Laundry Kitchen & Laundry
Kitchen & Laundry
Just 4 blocks from OSF!
Anne Hathaway House
7 Bedrooms
$349 - $1,644 / per night
Bedrooms 7 bedrooms
Bathrooms 8 baths
Guests 14 guests
The Barclay-Klum House is a 4-bedroom, 2-bath historic remodel located less than one mile from downtown Ashland. Modern design elements have been carefully integrated to complement the historical significance of the home. The results are stunning! The North Suite (Upper Floor) is a 2-bedroom, 1-bath unit with stunning 12-foot ceilings and tall wind
3 Minutes to Plaza 3 Minutes to Plaza
3 Minutes to Plaza
3 Minutes to Plaza ~ Charming Kitchen
Barclay-Klum House
4 Bedrooms
$249 - $1,244 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
The Barclay-Klum North Suite is a 2 bedroom, 1 bath historic remodel located less than one mile from downtown Ashland. Modern design elements have been carefully integrated to complement the historical significance of the home. The results are stunning! There is a queen-sized bed in the main bedroom and a full bed in the other bedroom. The bathroom
Charming Kitchen Charming Kitchen
Charming Kitchen
North (Upstairs) Suite~ 3 Minutes to Plaza ~ Charming Kitchen
Barclay-Klum North
2 Bedrooms
$149 - $844 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
The Barclay-Klum South Suite is a 2 bedroom, 1 bath historic remodel located less than one mile from downtown Ashland. Modern design elements have been carefully integrated to complement the historical significance of the home. The results are stunning! There is a king-sized bed in the main bedroom and two twin beds in the second bedroom. The bathr
Downstairs Suite Downstairs Suite
Downstairs Suite
South (Downstairs) Suite~3 Minutes to Plaza~ Kitchen
Barclay-Klum South
2 Bedrooms
$125 - $544 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace, large 'smart' flat screen television and plenty of seating. Outdoors enjoy the gardens and the large deck area with more seating and private parking.This house is just 5 blocks from the Oregon Shakespeare Festival. Guest
Gourmet Kitchen Gourmet Kitchen
Gourmet Kitchen
Just 5 Blocks from OSF~ Gourmet Kitchen
Blue Moon Compound
6 Bedrooms
$349 - $2,691 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 15 guests
History...Originally built as a farmhouse in the 1890’s, our Ashland, Oregon Inn has been hosting visitors to the area since 1991. It was named The Mouse Trap Inn as a nod to a historic (and now defunct) pine mousetrap factory in the city which once supplied 90% of the nation’s traps! Of course, with Ashland’s theatrical history, many visitors asso
5 Blocks to OSF 5 Blocks to OSF
5 Blocks to OSF
Pet Friendly ~ 5 Blocks to OSF
Blue Moon Cottage
1 Bedroom Pet Friendly
$125 - $444 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace, large 'smart' flat screen television and plenty of seating. Outdoors enjoy the gardens and the large deck area with more seating and private parking.This house is just 5 blocks from the Oregon Shakespeare Festival. Guest
Gourmet Kitchen Gourmet Kitchen
Gourmet Kitchen
Just Five Blocks from OSF!~ Gourmet Kitchen
Blue Moon House
5 Bedrooms
$249 - $1,244 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 11 guests
This spacious three bedroom historic home has been fully renovated, has brand new furnishings, and is perfect for up to 6 guests. Three private bedrooms all include king beds and plenty of space to relax. There are two full bathrooms, one of each floor. Enjoy the large, well-appointed kitchen with concrete countertops and gas stove. Also includes a
1 Mile -Shakespeare 1 Mile -Shakespeare
1 Mile -Shakespeare
1920's Modern Restoration ~ Sleeps 6~ One Mile to Shakespeare
Century House
3 Bedrooms
$174 - $1,044 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Courtside Cottage is a studio that sleeps four guests and includes a king size bed in the single bedroom with a comfortable sofa sleeper located in the living room area. The bathroom is quite large considering the size of the living space and accommodates two adults getting ready for the day easily. The private patio with outdoor dining table makes
Courtside Cottage
Studio Pet Friendly
$125 - $624 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32" flat panel smart tv, with wi-fi. There is a full kitchen with stove and oven, coffee maker
Downtown Ashland Downtown Ashland
Downtown Ashland
5 Blocks to Downtown Ashland ~Kitchen
Lori Lane - Juliet
2 Bedrooms
$125 - $524 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Lori Lane is a 5 bedroom, 3 and half bathroom, modern home that sleeps 10. Juliet Cottage can also be rented to increase the occupancy to 14. The primary bedroom has a king-sized bed and bathroom with shower en-suite. Four additional bedrooms have king and queen-sized beds, beautifully decorated with your absolute comfort in mind. Enjoy cozy firepl
Main Floor Bedroom Main Floor Bedroom
Main Floor Bedroom
5 blocks from Downtown Ashland ~Kitchen ~Main Floor Bedroom
Lori Lane Compound
7 Bedrooms
$344 - $2,115 / per night
Bedrooms 7 bedrooms
Bathrooms 4 baths
Guests 14 guests

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