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Our top choices for Ashland guest houses

1. Modern 1 BR Guest House in Central Point, OR. Your ideal Southern Oregon stopover! Features AC, full kitchen, W/D, and dedicated workspace. Quick and convenient access to I-5 and local attractions.

Modern 1 BR Guest House in Central Point, OR. Your ideal Southern Oregon stopover! Features AC, full kitchen, W/D, and dedicated workspace. Quick and convenient access to I-5 and local attractions.
Central Point
10.0 out of 10, Exceptional, (3 reviews)
"I loved the little house. Everything was first class, clean as a whistle, fully equipped and what a comfortable bed!! Will definitely stay here again. Love love loved it!!"
United States
Anonymous traveler
The price is AED 399
AED 624 total
includes taxes & fees
15 Nov - 16 Nov
Modern 1 BR Guest House in Central Point, OR. Your ideal Southern Oregon stopover! Features AC, full kitchen, W/D, and dedicated workspace. Quick and convenient access to I-5 and local attractions.

2. Charleen's Cottage~Couple Perfect!Great Location! A Gem!

Charleen's Cottage~Couple Perfect!Great Location! A Gem!
Jacksonville
10.0 out of 10, Exceptional, (251 reviews)
"The property was absolutely perfect for us. It was nothing to walk the brick festival and a fun café right down the street. Would absolutely stay there again."
United States
Kacy
The price is AED 397
AED 487 total
includes taxes & fees
16 Nov - 17 Nov
Charleen's Cottage~Couple Perfect!Great Location! A Gem!

3. Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking
Medford
8.0 out of 10, Very good, (1 review)
"We didn’t appreciate the fact that they waited until exactly 4pm to send the info on how to get into the house. We had someone dropping us off at the house and had to wait outside until they finally got back to us, even though we tried throughout the day multiple times. The skylight woke us up super early because it got very bright in our room. The house was clean and fit our family of 6 well."
United States
Stephanie F.
The price is AED 520
AED 1,010 total
includes taxes & fees
2 Dec - 3 Dec
Near Downtown- Kitchen-Washer/Dryer-Parking

4. Charming Wine Country Carriage House – 2BR/2BA near Jacksonville Peaceful retreat in the heart of Southern Oregon wine country. Private, comfy, and perfect for couples or friends. Close to wineries, trails & historic Jacksonville.

Charming Wine Country Carriage House – 2BR/2BA near Jacksonville Peaceful retreat in the heart of Southern Oregon wine country. Private, comfy, and perfect for couples or friends. Close to wineries, trails & historic Jacksonville.
Central Point
10.0 out of 10, Exceptional, (15 reviews)
"This property is truly a top-tier stay. It is exceptionally quiet, incredibly spacious, and thoughtfully designed to accommodate groups of all sizes. The home was spotless upon arrival and fully stocked with everything we needed, from a well-equipped kitchen to plenty of seating, linens, and other conveniences that made our stay comfortable and stress-free."
United States
David S.
The price is AED 535
AED 1,069 total
includes taxes & fees
13 Nov - 14 Nov
Charming Wine Country Carriage House – 2BR/2BA near Jacksonville Peaceful retreat in the heart of Southern Oregon wine country. Private, comfy, and perfect for couples or friends. Close to wineries, trails & historic Jacksonville.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Ashland

World-class Shakespeare performances unfold in outdoor theaters surrounded by mountain views from June through October. Lithia Park's trails wind along Ashland Creek, perfect for morning walks before browsing the downtown galleries and craft breweries.

A stone bridge over a calm stream with autumn leaves.

Top reviews in Ashland