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 85°F
Century House ~ 1920's Modern Restoration ~ Sleeps 6
$225/avg daily price

Century House ~ 1920’s Modern Restoration ~ Sleeps 6

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Savage Upon Siskiyou House ~ Downtown Ashland ~ Sleeps 8
$345/avg daily price

Savage Upon Siskiyou House ~ Downtown Ashland ~ Sleeps 8

  • 3
  • 2
  • 8
Savage Upon Siskiyou ~ Master Suite ~ Downtown Ashland
$125/avg daily price

Savage Upon Siskiyou ~ Master Suite ~ Downtown Ashland

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  • 1
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Savage Upon Siskiyou ~ Front House ~ Sleeps 6
$235/avg daily price

Savage Upon Siskiyou ~ Front House ~ Sleeps 6

  • 2
  • 1.5
  • 6
The House at Innsbruck Ridge ~ Sleeps 10
$350/avg daily price

The House at Innsbruck Ridge ~ Sleeps 10

  • 5
  • 3
  • 10
Anne Hathaway's House ~ Just 4 blocks from OSF!
$495/avg daily price

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

  • 7
  • 7.5
  • 13
The Barclay-Klum House ~ Sleeps 8
$450/avg daily price

The Barclay-Klum House ~ Sleeps 8

  • 4
  • 2
  • 8
The Barclay-Klum House ~ North (Upstairs) Suite
$225/avg daily price

The Barclay-Klum House ~ North (Upstairs) Suite

  • 2
  • 1
  • 4
Featured The Barclay-Klum House ~ North (Downstairs) Suite
$195/avg daily price

The Barclay-Klum House ~ South (Downstairs) Suite

  • 2
  • 1
  • 4
Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF
$225/avg daily price

Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF

  • 1
  • 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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  • 5
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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

  • 6
  • 6
  • 15
Courtside Cottage~5-minute walk from OSF~Dog Friendly
$195/avg daily price

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

  • 1
  • 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

  • 2
  • 1
  • 3
"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

  • 1
  • 1
  • 2
1910 Orchard Guest House & RV in Oregon Wine Country
$250/avg daily price

1910 Orchard Guest House & RV in Oregon Wine Country

  • 3
  • 2
  • 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

  • 2
  • 1
  • 5
Lori Lane House ~ 5 Blocks from Downtown Ashland
$575/avg daily price

Lori Lane House ~ 5 Blocks from Downtown Ashland

  • 5
  • 4
  • 10
Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown
$195/avg daily price

Lori Lanes ‘Juliet Cottage’ ~ 2 Bedroom ~ Downtown

  • 2
  • 1
  • 4
The Pioneer - Craftsman House - Closest to OSF!
$325/avg daily price

The Pioneer – Craftsman House – Closest to OSF!

  • 3
  • 2
  • 8
The Pioneer House -North Suite (Upstairs) - Closest to OSF!
$225/avg daily price

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

  • 2
  • 1
  • 6
The Pioneer House - South Suite (Downstairs) - Closest to OSF!
$325/avg daily price

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

  • 3
  • 2
  • 8
The Pioneer North & South - Closest to OSF!
$550/avg daily price

The Pioneer North & South – Closest to OSF!

  • 5
  • 3
  • 14
The Pioneer ~ Closest to OSF!
$875/avg daily price

The Pioneer ~ Closest to OSF!

  • 8
  • 5
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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

  • 3
  • 2
  • 6
Featured Straw Bale Retreat on Tolman Creek
$265/avg daily price

Straw Bale Retreat on Tolman Creek

  • 2
  • 1
  • 6
The Aloha House ~ Pool and Hot Tub
$225/avg daily price

The Aloha House ~ Hot Tub & Seasonal Pool

  • 2
  • 2
  • 4
Hidden Valley Retreat ~ Hot Tub ~ Sleeps 8
$225/avg daily price

Hidden Valley Retreat ~ Sleeps 8

  • 3
  • 1.5
  • 8
Featured Capital House ~Pool~ Quiet Stay Minutes from Downtown
$275/avg daily price

Capital House ~Pool~ Quiet Stay Minutes from Downtown

  • 3
  • 2
  • 6
Indigo Creek Loft
$135/avg daily price

Indigo Creek Loft

  • 1
  • 1
  • 2
Rustic Rogue Cottage ~ Private Views of Table Rock
$125/avg daily price

Rustic Rogue Cottage ~ Private Views of Table Rock

  • 2
  • 1
  • 6
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"The cottage is an absolute delight! The space is clean, fresh, and updated with thoughtful and smart features and amenities! It has everything you could need for your trip to Ashland and the location is too perfect, tucked in right next to downtown and a short and easy walk to everything! We thoroughly enjoyed our stay and hope to come back and stay here again in our future visits to Ashland!"

Quinlyn 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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