Southern Oregon Vacation Rentals

• Bedrooms: 3
• Bathrooms: 3
• Sleeps: 8

Enjoy your stay at Maxfield's, a turn of the century vintage home in Ashland, Oregon. Built in 1903...

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• Bedrooms: 2
• Bathrooms: 1
• Sleeps: 4

Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, ...

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• Bedrooms: 2
• Bathrooms: 2
• Sleeps: 6

Please note: Rates do not include food service and we do not accommodate pets. Two bedroom 1 1/2 ...

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• Bedrooms: 4
• Bathrooms: 3
• Sleeps: 10

Asian meets Craftsman in this two story hillside home perched high above the city lights. Full ...

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• Bedrooms: 1
• Bathrooms: 1
• Sleeps: 2

Nestled in the hills just above the Roxy Ann Winery and minutes from Roxy Ann Peak hiking trails, ...

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• Bedrooms: 2
• Bathrooms: 1
• Sleeps: 4

Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to ...

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• Bedrooms: 2
• Bathrooms: 2
• Sleeps: 5

Helman Guest House is a charming early 1900's two bedroom home that can comfortably sleep up to 5 ...

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• Bedrooms: 3
• Bathrooms: 2
• Sleeps: 8

Three freshly renovated farm houses in a cattle country setting with snow capped mountain back drop...

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• Bedrooms: 4
• Bathrooms: 2
• Sleeps: 16

Relax, refresh and "reboot" for a log cabin ranch vacation at the pristine Green Springs Box R ...

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• Bedrooms: 3
• Bathrooms: 2
• Sleeps: 10

Abbott's Cottages is proud to offer the "Avocet", a delightful three bedroom/two bath vacation ...

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• Bedrooms: 3
• Bathrooms: 2
• Sleeps: 7

The Rockhouse in Latakomie Shores on Agency Lake is the perfect place to stay for anyone in the ...

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• Bedrooms: 1
• Bathrooms: 1
• Sleeps: 2

Bed and Breakfast: The Settlement Steve and Debbie enjoy sharing their home. The two guest bedrooms...

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• Bedrooms: 3
• Bathrooms: 2
• Sleeps: 7

The Mountain-View House is an nearly brand new, spacious three bedroom two bath house overlooking ...

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• Bedrooms: 1
• Bathrooms: 1
• Sleeps: 2

Cottage, 1 bedroom, 1 bath (Sleeps 2) Country cottage above detached garage less than 10 minutes ...

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• Bedrooms: 6
• Bathrooms: 4
• Sleeps: 14

Location & Luxury! Just a block from town and renowned Oregon Shakespeare Festival and.easy ...

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• Bedrooms: 3
• Bathrooms: 2
• Sleeps: 7

The Lakeview House is an nearly brand new, spacious three bedroom two bath house overlooking Agency...

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• Bedrooms: 1
• Bathrooms: 1
• Sleeps: 2

The Pine Street Cottage, operated by Country House Inns Jacksonville, is located one block from the...

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• Bedrooms: 2
• Bathrooms: 1
• Sleeps: 4

Find Ashland Vacation Rentals on FlipKeyWelcome to the ArtYCottage nestled in the Cascade foothills...

per night

• Bedrooms: 3
• Bathrooms: 1
• Sleeps: 8

Relax, refresh and "reboot" for a log cabin ranch vacation at the pristine Green Springs Box R ...

per night

• Bedrooms: 3
• Bathrooms: 2
• Sleeps: 6

The idyllic chalet nestled in the pines of Latakomie Shores, with a private park and beach just ...

per night