Ashland Guest Houses

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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.

Central Point

Rod B.

includes taxes & fees

14 Sept - 15 Sept

2. 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

Pamela S.

includes taxes & fees

17 Aug - 18 Aug

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

Jacksonville

Varun

includes taxes & fees

14 Sept - 15 Sept

Coffee/tea maker, fridge, microwave, oven

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

Medford

includes taxes & fees

14 Sept - 15 Sept

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Top Ashland Hotel Reviews

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Great location to Shakespeare Theatre and close to the park, restaurant and all other stores, gift shops. The breakfast was great and the area was very quiet and nice. The only thing might be mentioned that body washer and shampoo is so small to use with even 2 persons. Better be provided with enough quantities for reservated number of persons. Otherwise I loved to stay here with my son for Shaspeares performance."

Ashland Hills Hotel & Suites

10/10 Excellent

"As sprawling Ashland Hills is well-designed to host large events, it isn't the place one would go for intimacy or charm, or walking access to downtown. But it's a perfect place to go if you like spacious, clean rooms and comfortable beds (with soft pillows!), and easy access to parking, pool, tennis courts, a large, fenced dog area for my Golden Retriever - and beautiful views if you ask in advance. Too tired to venture out, I was somewhat surprised to be able to order a dinner with perfectly cooked wild salmon! (I'm guessing that a real espresso bar would be a popular addition, but there are plenty within a 5 minute drive.)"

Callahan's Mountain Lodge

10/10 Excellent

"Callahans is a southern Oregon institution. I have been going to this resort in the mountains for over a half century. My wife and I spent the night, had dinner and breakfast: we watched the Perseid meteor shower from the top of nearby Mt Ashland. From cocktails on the wonderful expansive decks to a tasty scallop dinner choice, it was a wonderful evening….. The room was standard but was expansive and tastefully decorated with mountain themes. The staff truly wanted us to have a great time. Consider this resort for a mountain get away……"

Timbers INN and Suites

8/10 Good

"Great service from Gurpik (not sure I've spelled his name right...), who moved me to a ground-floor room so I could secure my bike overnight. The pool—small, but refreshing—was very nice after a long day's drive in hot summer temperatures. The pizza place right next door is also a nice "amenity," good pizza and beer. Had a good night's sleep after the family right over my room upstairs quieted down, lot of noise from running but did not go on too late. All in all, very good value for a place tp stop over in Ashland."

Palm Cottages

10/10 Excellent

"The room was very clean, something as a former maid I always look for. Staff was very helpful. We loved the soaps and staff was great about finding which particular soap brand used and even a store location for us. Motel was quiet at night and the beds were very comfortable. Kitchenette was perfect for our needs, we didn't plan to cook any meals but morning tea and coffee were much appreciated. The atmosphere was the best, quirky, retro, but not weirdly so, with peaceful colors and beautiful artwork. The patio area is stunning, a work of art. In all, if we come back to Ashland for more Shakespeare Festival fun the PALM will be our first choice for lodging! Oh, and seeing a deer calmly grazing on the wildflowers added to the fun!"

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