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Downtown Ashland
and
Greater Jackson County

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.

Century House ~ 1920's Modern Restoration ~ Sleeps 6

^$225_{/avg daily price}

Century House ~ 1920’s Modern Restoration ~ Sleeps 6

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2
6

The House at Innsbruck Ridge ~ Sleeps 10

^$350_{/avg daily price}

The House at Innsbruck Ridge ~ Sleeps 10

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Anne Hathaway's House ~ Just 4 blocks from OSF!

^$495_{/avg daily price}

Anne Hathaway’s House ~ Just 4 blocks from OSF!

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7.5
13

Featured

The Barclay-Klum House

^$195_{/avg daily price}

The Barclay-Klum House

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1
4

Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF

^$225_{/avg daily price}

Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF

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1
4

Blue Moon House ~ Just Five Blocks from OSF!

^$575_{/avg daily price}

Blue Moon House ~ Just Five Blocks from OSF!

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Blue Moon House & Cottage ~ Just 5 Blocks from OSF

^$800_{/avg daily price}

Blue Moon House & Cottage ~ Just 5 Blocks from OSF

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Courtside Cottage~5-minute walk from OSF~Dog Friendly

^$195_{/avg daily price}

Courtside Cottage~5-minute walk from OSF~Dog Friendly

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4

The 1910 Orchard Guest House ~ In the Foothills of Wine Country

^$145_{/avg daily price}

The 1910 Orchard Guest House ~ In the Foothills of Wine Country

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"Sky is the Limit" 5th Wheel in Oregon's Wine Country

^$119_{/avg daily price}

“Sky is the Limit” 5th Wheel in Oregon’s Wine Country

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1910 Orchard Guest House & RV in Oregon Wine Country

^$250_{/avg daily price}

1910 Orchard Guest House & RV in Oregon Wine Country

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5

Hound's Landing #A~A dog's walk to OSF~Pet Friendly

^$225_{/avg daily price}

Hound’s Landing #A~A dog’s walk to OSF~Pet Friendly

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1
5

Lori Lane House ~ 5 Blocks from Downtown Ashland

^$575_{/avg daily price}

Lori Lane House ~ 5 Blocks from Downtown Ashland

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Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown

^$195_{/avg daily price}

Lori Lanes ‘Juliet Cottage’ ~ 2 Bedroom ~ Downtown

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1
4

The Pioneer - Craftsman House - Closest to OSF!

^$325_{/avg daily price}

The Pioneer – Craftsman House – Closest to OSF!

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2
8

The Pioneer House -North Suite (Upstairs) - Closest to OSF!

^$225_{/avg daily price}

The Pioneer House -North Suite (Upstairs) – Closest to OSF!

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1
6

The Pioneer House - South Suite (Downstairs) - Closest to OSF!

^$325_{/avg daily price}

The Pioneer House – South Suite (Downstairs) – Closest to OSF!

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2
8

The Pioneer North & South - Closest to OSF!

^$550_{/avg daily price}

The Pioneer North & South – Closest to OSF!

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3
14

The Pioneer ~ Closest to OSF!

^$875_{/avg daily price}

The Pioneer ~ Closest to OSF!

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5
22

Spur Rail Loft House~ Just a few blocks to Downtown Ashland

^$195_{/avg daily price}

Spur Rail Loft House~ Just a few blocks to Downtown Ashland

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2
6

Featured

Straw Bale Retreat on Tolman Creek

^$265_{/avg daily price}

Straw Bale Retreat on Tolman Creek

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1
6

The Aloha House ~ Pool and Hot Tub

^$225_{/avg daily price}

The Aloha House ~ Hot Tub & Seasonal Pool

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2
4

Hidden Valley Retreat ~ Hot Tub ~ Sleeps 8

^$225_{/avg daily price}

Hidden Valley Retreat ~ Hot Tub ~ Sleeps 8

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1.5
8

Featured

Capital House ~Pool~ Quiet Stay Minutes from Downtown

^$275_{/avg daily price}

Capital House ~Pool~ Quiet Stay Minutes from Downtown

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2
6

Indigo Creek Loft

^$135_{/avg daily price}

Indigo Creek Loft

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Rustic Rogue Cottage ~ Private Views of Table Rock

^$125_{/avg daily price}

Rustic Rogue Cottage ~ Private Views of Table Rock

2
1
6

"Wow! We've been Airbnb hosts & stayed in many places and this is definitely at the top of the list. It is easy walking to just about anywhere you need to go. It has it's own parking space which can be invaluable in Ashland. Time for me to stop & you to go, this is a good one."

Mitch and Susan June 8, 2020

Area Attractions & Vendors

local dining

Paddington Station

local specialty shop

Pelindaba Lavender

local photography

Cornelius Matteo Photography
Family Vacation Portrait Photography

local dining

Ostras Restaurant

local dining

Standing Stone Restaurant

local theater or performance

Oregon Shakespeare Festival

local theater or performance

Oregon Cabaret Theater

local theater or performance

Camelot Theater

local bakery

local dining

Harvey’s Place

local winery

local winery

Search

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