Pets allowed:
Wi-Fi available:

Description from owner

Ashland's favorite family inn! Oak Street Cottages are located just a block from downtown Ashland, the Shakespeare Festival, the Plaza, and beautiful Lithia Park. Four houses sleep from 6 to 11 people, fully furnished, complete with private parking, patios, and homey touches. Enjoy the fireplace and indoor whirlpool tub-for-two in some cottages. We specialize in children of all ages! Pets welcome with prior approval and deposit. Handicapped-accessible cottage sleeps 6.

NOTE! The availability calendar on this site shows if we have openings in all 4 of our cottages (it is marked out if all 4 are booked)please see our online site for individual cottage availability.

Let Oak Street Cottages be your family's "home away from home"!

Beds: 2 Queen Beds, 5 Twin Beds, 1 Sofa Bed, 2 Cribs

TripAdvisor Property ID: 8610364

About the area

Oak Street Cottages are nestled in downtown Ashland, just one block from the Oregon Shakespeare Festival theaters, in the heart of the "new Ashland" art district! Over 20 restaurants and art galleries are within a 3-block walk of our four homey cottages! Says one of our guests:"What a quiet and pleasant retreat in the center of this magical town. We love it!" E. Miller

Owner profile

Constance D.

Languages spoken: English



  • Air conditioning
  • Balcony/Terrace
  • Grill
  • Heating
  • Balcony/Terrace
  • Fireplace
  • High Speed Internet
  • Linen provided
  • Parking Included
  • Balcony/Terrace
  • Pet Friendly
  • Wheelchair users


  • Ceiling Fans
  • Dishwasher
  • DVD player
  • Hair dryer
  • Iron
  • CD player
  • Refrigerator
  • Satellite TV
  • Microwave
  • Stove
  • Telephone
  • Toaster
  • Video player


  • Cycling Trips
  • Water sports
  • Horse riding

Reviews (6)

Very Good – based on 6 reviews Very Good
6 reviews

“Perfect location!”

Reviewed 29 Sep 2015

The cottage was exactly as advertised and pictured. Maybe even better! The minute we opened the door and smelled the fresh baked cinnamon bread we knew we were on to something. And the location could not be more ideal. We would stay here again in a heartbeat. Thank you!!

Owner's reply: Thanks, Linda and family! It's always nice to have new guests to introduce to the Oak Street many of our guests are returning now, some of them for 22 years! Glad to have you with us! Constance, Manager

“Excellent location, room for everyone”

Reviewed 1 Mar 2011

We were pleasantly surprised that this little cottage really had beds for all 9 (plus infant) of us, and still had an empty sofa/bed if we had more. The kitchen is small, but stocked well. Dining room table really could fit us as well. So it was easy to cook meals here together. 1-2 blocks to everything in town (theatre & restaurants), made it the perfect location for our ski & theatre trip to Ashland.

“Our stay at Oak Street Cottage”

Reviewed 28 Dec 2010

We were very pleased with our experience. They thought of everything to make our stay comfortable and relaxing.

“Just Right”

Reviewed 16 Apr 2010

The cottage was just what we needed to accommodate our Board of Directors for sleeping arrangements and meeting space. It was comfortable, spacious, tastefully decorated, and homey. The freshly baked bread that greeted us upon arrival was a nice touch. The only drawback was a difficulty in parking.

“Wonderful Location”

Reviewed 3 Sep 2008

Constance, Thank you so much for accomodating us at the last minute. We had a wonderful time at your cottage. It was quaint, cozy and quiet.The location to downtown was perfect.It couldn't have been closer. We would love to come back and will definitely recommend you to all our friends and relatives. Kind regards, Kelly Rodrigo and Family

“Excellent Accommodations”

Reviewed 24 May 2008

The cottage was as represented and in a perfect location. We had a great time, appreciated the home baked bread that greeted us upon arrival, and can't think of anything that would have made it better. Thank you.

Review 1-6 of 6
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