Ashland Cottage Rentals By Owner

Ashland Cottage Rentals

Highly Rated

Cottage

The Ashland Cottage, walk to town

10.0

Exceptional

(226 Reviews)

1 Bedroom 1 Bath 4 Guests 600 ft²

R4,807/Night 7 Nights - R33,656

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Bluemoon Vacation Rentals - Bluemoon Cottage

House

Bluemoon Vacation Rentals - Bluemoon Cottage

9.0

Exceptional

(8 Reviews)

1 Bedroom 1 Bath 4 Guests 850.35 ft²

R4,332/Night 7 Nights - R30,324

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Stacy's 2nd St Cottage. Steps to downtown.

Highly Rated

Cottage

Stacy's 2nd St Cottage. Steps to downtown.

10.0

Exceptional

(98 Reviews)

2 Bedrooms 1 Bath 4 Guests 1200 ft²

R6,828/Night 7 Nights - R47,797

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Warm and Inviting Ashland Cottage Less Than Half-Mile to SOU

House

Warm and Inviting Ashland Cottage Less Than Half-Mile to SOU

1 Bedroom 1 Bath 2 Guests 462.85 ft²

R2,482/Night 7 Nights - R17,375

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Highly Rated

Cottage

The Terra Cottage Inn - Ashland, Oregon

10.0

Exceptional

(73 Reviews)

2 Bedrooms 1 Bath 4 Guests 600 ft²

R3,642/Night 7 Nights - R25,491

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New

House

Sunset Cottage at Grizzly Peak Winery

1 Bedroom 1 Bath 4 Guests

R4,200/Night 7 Nights - R29,394

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High Street Cottage Artists' Garden Cottage Clean & Beautiful

Highly Rated

Cottage

High Street Cottage Artists' Garden Cottage Clean & Beautiful

10.0

Exceptional

(71 Reviews)

2 Bedrooms 1 Bath 4 Guests 800 ft²

R3,778/Night 7 Nights - R26,454

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House

Cozy Modern Cottage

1 Bedroom 1 Bath 2 Guests 602.78 ft²

R4,046/Night 7 Nights - R28,316

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Courtside Cottage - WalkScore 93 - Dog Friendly

Highly Rated

Cottage

Courtside Cottage - WalkScore 93 - Dog Friendly

10.0

Exceptional

(62 Reviews)

1 Bedroom 1 Bath 4 Guests

R3,644/Night 7 Nights - R25,507

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Cottage

Charming, Comfortable Garden Studio Above The University.

10.0

Exceptional

(22 Reviews)

1 Bedroom 1 Bath 3 Guests 385 ft²

R1,204/Night 7 Nights - R8,426

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Charming well appointed Cottage in Ashland (800 + sq. ft.)

Price Dropped

Cottage

Charming well appointed Cottage in Ashland (800 + sq. ft.)

10.0

Exceptional

(18 Reviews)

1 Bedroom 1 Bath 2 Guests 800 ft²

R2,658/Night 7 Nights - R18,600

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Cottage

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

10.0

Exceptional

(7 Reviews)

2 Bedrooms 2 Baths 4 Guests

R6,628/Night 7 Nights - R46,393

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More Top-Rated Cottage Rentals in Ashland Area

Why Choose Rent By Owner for your Ashland Cottage Rentals?

What makes our Cottage Rentals special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Ashland

How to Book Your Ashland Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Ashland

More Top-Rated Cottage Rentals in Ashland Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Ashland, OR

Tashi Choling Buddhist Center

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Ariel Ski Lift

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Windsor Ski Lift

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Mount Ashland Ski Area

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Comer Ski Lift

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Ashland Library

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North Mountain Park

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Southern Oregon University

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Skidmore Academy Historic District

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Historic Downtown District

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Historic Railroad District

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Siskiyou-Hargadine Historic District

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Frequently Asked Questions About Ashland Rental Cottages

1. What are the top Cottages in Ashland?

There are a lot of options in Ashland. If you plan on staying in the Ashland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Ashland:

2. How many Cottages are available in Ashland?

Currently, the total number of properties listed by RBO in 2026 is over 40 in the Ashland area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Ashland. 