Downtown Ashland Oregon Rentals

Downtown Ashland Oregon

BookStayHop offers the best vacation rentals and cabins in the area. Check our Downtown Ashland Oregon Rentals below. We are sure you will find the perfect fit for your family vacation! Our Downtown Ashland Oregon Rentals are located in the heart of Ashland, surrounded by restaurants, theaters and more.

Downtown and the surrounding neighborhoods offer visitors the best of both worlds. A short walk away from Ashland’s wonderful restaurants, art galleries and shops where you can people-watch from many sidewalk cafes, or enjoy a stroll through Lithia Park. Conveniently located near I-5 and all amenities, Downtown Ashland Oregon is a great place to visit!

If you are planning to book a cabin please browse our Green Springs Inn Cabins and Hyatt Praire Cabins. We have the best selection in the area at the best rates! 



Properties Available 29 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 -
$349 - $999 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (1)
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 -
$502 - $1,644 / per night
Bedrooms 7 bedrooms
Bathrooms 8 baths, 1 half bath
Guests 14 guests
Rating 5 (4)
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
$163 - $844 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
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
$609 - $1,244 / 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
$151 - $399 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
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
$437 - $789 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 11 guests
Welcome to Casa Amore Cottage in the heart of Ashland's Historic Railroad District. Stroll to coffee shops, restaurants, shopping and the world famous Oregon Shakespeare Festival from this eclectic neighborhood of vintage 1800's homes, businesses and cottages. This two story cottage features a king bedroom suite with full bathroom upstairs, and que
NEW! NEW!
NEW!
Casa Amore Cottage
1 Bedroom - Pet Friendly
$133 - $444 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath, 1 half bath
Guests 4 guests
Rating 5 (1)
Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival, boutique shops, award-winning wineries, and restaurants Ashland is famous for, Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer.Two studio cottages are available separately behind the house off the brick t
2 Blocks to Downtown 2 Blocks to Downtown
2 Blocks to Downtown
2 Blocks to Downtown
Helman House
2 Bedrooms -
$169 - $399 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (2)
Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival, boutique shops, award-winning wineries, and restaurants Ashland is famous for, Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer.If you’re looking for privacy, comfort, and convenience, look no further than
NEW! NEW!
NEW!
Helman House Studio A
Studio
$118 - $224 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 3 guests
Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival, boutique shops, award-winning wineries, and restaurants Ashland is famous for, Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer. If you’re looking for privacy, comfort, and convenience, look no further tha
NEW! NEW!
NEW!
Helman House Studio B
Studio
$114 - $217 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 3 guests
Your reservation will include the Helman House and two cottages (sleeps 10). Updated with all modern amenities, Helman House boasts two largebedrooms, a king-size bed downstairs and two kings upstairs, two full baths, and a basic kitchen for light & simple meal preparation. Enjoy the bright kitchen nook for your sunny morning coffee or a long s
NEW! NEW!
NEW!
Helman Mega
4 Bedrooms
$323 - $636 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 13 guests
Convenient to the many theaters—including the world-renowned Oregon Shakespeare Festival—, boutique shops, award winning wineries, and restaurants Ashland is famous for, Helman House is a home away from home for visitors eager to experience all Southern Oregon has to offer. If you’re looking for privacy, comfort, and convenience, look no further th
NEW! NEW!
NEW!
Helman Studios A and B
2 Bedrooms
$143 - $274 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

Tell us what you're looking for and someone will contact you with available options.

I agree