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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Guest Houses in Ashland and around

Our top choices for Ashland guest houses

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.
Dining

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.

10.0 out of 10, Exceptional, (8)
"Huge, comfortable, beautiful property- such a relaxing spot. My son and I enjoyed the peace and quiet. This rental has every amenity one could need, was clean, and exceeded our expectations! The location was ideal, close to Medford and Jacksonville. We hope to come enjoy this space again!!"
The price is €353
includes taxes & fees
25 Aug - 26 Aug
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.
Sleek Modern ADU conveniently located near I-5.
Exterior detail

Sleek Modern ADU conveniently located near I-5.

The price is €174
includes taxes & fees
23 Sept - 24 Sept
Sleek Modern ADU conveniently located near I-5.
Near Downtown Studio-Parking-SmartTV -Kitchenette
Exterior detail

Near Downtown Studio-Parking-SmartTV -Kitchenette

10.0 out of 10, Exceptional, (2)
"Nicely decorated, updated and comfortable. ."
The price is €133
includes taxes & fees
24 Aug - 25 Aug
Near Downtown Studio-Parking-SmartTV -Kitchenette
Charleen's Cottage~Couple Perfect!Great Location! A Gem!
Exterior

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

9.8 out of 10, Exceptional, (167)
"Very nice cottage to stay at. Comfortable and clean with everything that you need."
The price is €117
includes taxes & fees
10 Sept - 11 Sept
Charleen's Cottage~Couple Perfect!Great Location! A Gem!
Near Downtown- Kitchen-Washer/Dryer-Parking
Fridge, microwave, oven, stovetop

Near Downtown- Kitchen-Washer/Dryer-Parking

9.6 out of 10, Exceptional, (15)
"The house is secluded, lovely and well stocked. The managers were quick to answer questions and very helpful. I would definitely stay there again."
The price is €167
includes taxes & fees
1 Sept - 2 Sept
Near Downtown- Kitchen-Washer/Dryer-Parking
Near Downtown- Kitchen-Washer/Dryer-Parking
Fridge, microwave, oven, stovetop

Near Downtown- Kitchen-Washer/Dryer-Parking

The price is €237
includes taxes & fees
2 Sept - 3 Sept
Near Downtown- Kitchen-Washer/Dryer-Parking
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.
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Top Ashland Hotel Reviews

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

10/10 Excellent
"So clean and a lovely indoor pool. Very pleased. "
Patricia 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Ashland by IHG