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.

Current Weather 50°F
Big Sky Cabin~ in Town ~ Family & Pet Friendly

Big Sky Cabin~ in Town ~ Family & Pet Friendly

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Garden Creek ~ Downtown Jacksonville ~ Pet Friendly

Garden Creek ~ Downtown Jacksonville ~ Pet Friendly

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California Cottage ~ Downtown Jacksonville ~ Pet Friendly

California Cottage ~ Downtown Jacksonville ~ Pet Friendly

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Safari Studio ~ Downtown Jacksonville~ Pet Friendly

Safari Studio ~ Downtown Jacksonville~ Pet Friendly

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Peerless Entire Hotel ~ Downtown Ashland

Peerless Entire Hotel ~ Downtown Ashland

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Peerless Hotel ~ Guest Room 1 ~ Downtown Ashland

Peerless Hotel ~ Guest Room 1 ~ Downtown Ashland

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Peerless Hotel~ Guest Room 2 ~Downtown Ashland

Peerless Hotel~ Guest Room 2 ~Downtown Ashland

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Peerless Hotel~ Suite 3 ~ Downtown Ashland

Peerless Hotel~ Suite 3 ~ Downtown Ashland

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Peerless Hotel~ Guest Room 5 ~Downtown Ashland

Peerless Hotel~ Guest Room 5 ~Downtown Ashland

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Peerless Hotel~ Guest Room 6~ Downtown Ashland

Peerless Hotel~ Guest Room 6~ Downtown Ashland

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Peerless Hotel~ Suite 7 ~Downtown Ashland

Peerless Hotel~ Suite 7 ~Downtown Ashland

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Century House ~ 1920's Modern Restoration ~ Sleeps 6

Century House ~ 1920’s Modern Restoration ~ Sleeps 6

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Savage Upon Siskiyou House ~ Downtown Ashland ~ Sleeps 8

Savage Upon Siskiyou House ~ Downtown Ashland ~ Sleeps 8

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Savage Upon Siskiyou ~ Master Suite ~ Downtown Ashland

Savage Upon Siskiyou ~ Master Suite ~ Downtown Ashland

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Savage Upon Siskiyou ~ Front House ~ Sleeps 6

Savage Upon Siskiyou ~ Front House ~ Sleeps 6

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Red Hawk Hideaway ~ Saltwater Pool

Red Hawk Hideaway ~ Saltwater Pool~ Sleeps 6

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The House at Innsbruck Ridge ~ Sleeps 10

The House at Innsbruck Ridge ~ Sleeps 10

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

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

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The Barclay-Klum House ~ Sleeps 8

The Barclay-Klum House ~ Sleeps 8

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The Barclay-Klum House ~ North (Upstairs) Suite

The Barclay-Klum House ~ North (Upstairs) Suite

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Featured The Barclay-Klum House ~ North (Downstairs) Suite

The Barclay-Klum House ~ South (Downstairs) Suite

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Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF

Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF

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Blue Moon House ~ Just Five Blocks from OSF!

Blue Moon House ~ Just Five Blocks from OSF!

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Blue Moon House & Cottage ~ Just 5 Blocks from OSF

Blue Moon House & Cottage ~ Just 5 Blocks from OSF

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

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

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Madrona Lane Cottage ~ Countryside

Madrona Lane Cottage ~ Countryside

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Lori Lane House ~ 5 Blocks from Downtown Ashland

Lori Lane House ~ 5 Blocks from Downtown Ashland

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Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown

Lori Lanes ‘Juliet Cottage’ ~ 2 Bedroom ~ Downtown

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The Pioneer - Craftsman House - Closest to OSF!

The Pioneer – Craftsman House – Closest to OSF!

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

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

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

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

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The Pioneer North & South - Closest to OSF!

The Pioneer North & South – Closest to OSF!

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The Pioneer ~ Closest to OSF!

The Pioneer ~ Closest to OSF!

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

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

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Featured Straw Bale Retreat on Tolman Creek

Straw Bale Retreat on Tolman Creek

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The Aloha House ~ Pool and Hot Tub

The Aloha House ~ Hot Tub & Seasonal Pool

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Hidden Valley Retreat ~ Hot Tub ~ Sleeps 8

Hidden Valley Retreat ~ Sleeps 8

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Featured Capital House ~Pool~ Quiet Stay Minutes from Downtown

Capital House ~Pool~ Quiet Stay Minutes from Downtown

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Indigo Creek Loft

Indigo Creek Loft

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Rustic Rogue Cottage ~ Private Views of Table Rock

Rustic Rogue Cottage ~ Private Views of Table Rock

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Load More

“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

Mix Bakeshop

local dining

Harvey’s Place

local winery

Paschal Winery

local winery

Rellik Winery

local hiking

Hills & Valleys Outdoor Adventures

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