Southern Oregon Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Southern Oregon, Oregon, USA

The Ashland Cottage, walk to town
10.0 (219 Reviews)
1 Bedroom 4 Guests
Swank House on Main St in Ashland
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10.0 (5 Reviews)
2 Bedrooms 4 Guests
Barclay Klum House by WanderLodges
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10.0 (8 Reviews)
1 Bedroom 2 Guests
Hanna`s House | Downtown Retreat, Steps to OSF
10.0 (170 Reviews)
1 Bedroom 4 Guests
The Mountain Ave House by WanderLodges
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10.0 (7 Reviews)
1 Bedroom 2 Guests
The Barn at Emigrant Creek
FromR2,669 per night
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10.0 (2 Reviews)
2 Bedrooms 6 Guests
Grandview of Ashland
FromR8,043 per night
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10.0 (5 Reviews)
1 Bedroom 2 Guests
The Perfect Vacation Cottage
FromR6,562 per night
10.0 (118 Reviews)
2 Bedrooms 4 Guests
Custom Ashland Home with Fantastic Mountain Views
10.0 (101 Reviews)
2 Bedrooms 4 Guests
Bluemoon Vacation Rentals - Bluemoon House
10.0 (1 Review)
5 Bedrooms 11 Guests
Stacy's 2nd St Cottage. Steps to downtown.
10.0 (96 Reviews)
2 Bedrooms 4 Guests
Casa Amore~Pet-Friendly~Walkable
10.0 (1 Review)
1 Bedroom 4 Guests
Serene Family Cottage-minutes to Downtown
10.0 (1 Review)
1 Bedroom 5 Guests
RedTail Inn - 3 Suites Sleeps up to 12
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9.8 (13 Reviews)
8 Bedrooms 24 Guests
Abigail's Bed and Breakfast Inn
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9.7 (49 Reviews)
7 Bedrooms 14 Guests
The Terra Cottage Inn - Ashland, Oregon
10.0 (72 Reviews)
2 Bedrooms 4 Guests
Mahar Homes - Plaza North on First
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9.7 (3 Reviews)
7 Bedrooms 22 Guests
High Street Cottage Artists' Garden Cottage Clean & Beautiful
10.0 (71 Reviews)
2 Bedrooms 4 Guests
Barclay Klum House by WanderLodges
FromR7,508 per night
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9.4 (10 Reviews)
2 Bedrooms 4 Guests
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 (62 Reviews)
1 Bedroom 4 Guests
The Matriarch Suites- Downtown Ashland, OR
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9.2 (43 Reviews)
3 Bedrooms 6 Guests
The Mountain House by WanderLodges
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9.2 (38 Reviews)
3 Bedrooms 6 Guests
Helman Street Penthouse with a View
10.0 (37 Reviews)
2 Bedrooms 4 Guests
European Style Straw Bale Retreat
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9.2 (4 Reviews)
2 Bedrooms 8 Guests
Arden Forest Inn
FromR2,984 per night
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9.1 (123 Reviews)
6 Bedrooms 12 Guests
The Ashland Social | Guest Studio
FromR3,371 per night
10.0 (25 Reviews)
1 Bedroom 2 Guests
Charming well appointed Cottage in Ashland (800 + sq. ft.)
10.0 (18 Reviews)
1 Bedroom 2 Guests
Bluemoon Vacation Rentals - Bluemoon Cottage
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9.0 (8 Reviews)
1 Bedroom 4 Guests
Hanna's House by WanderLodges
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9.0 (2 Reviews)
1 Bedroom 4 Guests
East Main Ease!
10.0 (15 Reviews)
2 Bedrooms 6 Guests
Top floor of modern duplex - walk to plays, SOU, Lithia Park
10.0 (13 Reviews)
1 Bedroom 2 Guests
The Matriarch Heritage House- Downtown Ashland
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8.0 (1 Review)
2 Bedrooms 4 Guests
Hanna's House by WanderLodges
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10.0 (3 Reviews)
1 Bedroom 2 Guests
Downtown Ashland House - Walk to Plaza and OSF!
9.8 (45 Reviews)
2 Bedrooms 8 Guests
Arden Forest Inn
FromR3,512 per night
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9.8 (103 Reviews)
1 Bedroom 2 Guests
Ashland's Mountain View Vacation Rental.
9.8 (42 Reviews)
2 Bedrooms 6 Guests
Grandview of Ashland
FromR15,934 per night
New
1 Bedroom 6 Guests
A Cowslip's Belle Inn
FromR3,697 per night
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9.8 (41 Reviews)
1 Bedroom 3 Guests
Sunset Cottage at Grizzly Peak Winery
New
1 Bedroom 4 Guests
Swank House in Downtown Ashland
9.8 (6 Reviews)
2 Bedrooms 4 Guests
Cozy Modern Cottage
New
1 Bedroom 2 Guests
Bayberry Inn B&B and Oregon Wellness Retreat
10.0 (12 Reviews)
6 Bedrooms 12 Guests
The Columbia Hotel
9.7 (3 Reviews)
5 Bedrooms 4 Guests
Winchester Inn
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9.4 (407 Reviews)
22 Bedrooms 49 Guests
Swank Boutique Suites
9.4 (43 Reviews)
7 Bedrooms 8 Guests
Swank House- Downtown Suite-Pet Friendly
9.4 (12 Reviews)
1 Bedroom 2 Guests
Chateau Herb ~ Miranda Carriage House Apt
9.6 (5 Reviews)
2 Bedrooms 4 Guests
The Peerless Hotel
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9.2 (184 Reviews)
6 Bedrooms 12 Guests

About Southern Oregon Vacation Rentals

With more than 347 Southern Oregon vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Southern Oregon.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Southern Oregon, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Southern Oregon. Places to stay near Southern Oregon are 654.08 ft² on average, with prices averaging R4,782 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Southern Oregon with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Southern Oregon?

What are the top vacation rentals in Southern Oregon?

How many Rentbyowner vacation rentals are available in Southern Oregon?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 347 in the Southern Oregon area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Southern Oregon.