Ashland theaters are a block away!

Oak Street Cottages, Ashland\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\'s Favorite Family In
“ Excellent ”
6 Reviews
171 Oak St, Ashland, OR 97520


Bedrooms: 4
Bathrooms: 2
Sleeps: 11
Type: Cottage
Per night: $350
Per week: $2,100
Pets allowed: Yes
Internet: Yes
Description of the Ashland vacation cottage rental
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"!
Area Information
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

Availability Calendar


Begins Ends Week
Weekly Monthly Min
Jan 01 2014 Dec 31 2015 $350 $350 $2,100 - 2 Nights
Check In: 4 p.m. Check Out: 10 a.m.
Lodging tax: 10%
Deposits: Deposit of $250 required within 10 days to hold reservation. Balance of stay is due 30 days prior to arrival.
Payment Options: American Express, Mastercard, Personal Check, Visa
Other Fees: Dog deposit (by request only), $50, plus $150 minimum damage fee.


  • Beds

  • 2 Queen Beds
  • 5 Twin Beds
  • 1 Sofa Bed
  • 2 Cribs
  • Features

  • Air Conditioning
  • Fireplace
  • High Speed Internet
  • Patio
  • Balcony
  • Full Kitchen
  • Housekeeper
  • Pet Friendly
  • Beach Chairs
  • Hardwood Floors
  • Linens Provided
  • Porch
  • Beach Towels
  • Heating
  • Parking Included
  • Wheelchair Accessible
  • Deck
  • Appliances

  • Alarm Clock
  • Coffee Maker
  • Microwave
  • TV (Cable/Satellite)
  • Blender
  • DVD Player
  • Oven
  • Telephone
  • CD Player
  • Dishwasher
  • Radio
  • Toaster
  • Ceiling Fan
  • Hair Dryer
  • Refrigerator (Full)
  • VCR
  • Charcoal Grill
  • Iron
  • Stove
  • Activities

  • Bicycling
    (<1 mile)
  • Restaurant
    (<1 mile)
  • Volleyball Court
    (2 miles)
  • Cross-Country Skiing
    (10 miles)
  • Grocery Store
    (<1 mile)
  • Shopping Area
    (<1 mile)
  • Golf
    (3 miles)
  • Fishing
    (10 miles)
  • Hiking
    (<1 mile)
  • Gym/Fitness Center
    (1 mile)
  • Horseback Riding
    (5 miles)
  • Miniature Golf
    (10 miles)
  • Ice Skating
    (<1 mile)
  • Pool
    (1 mile)
  • Jet Skiing
    (5 miles)
  • Snowmobiling
    (10 miles)
  • Live Entertainment
    (<1 mile)
  • Racquetball
    (1 mile)
  • Lake
    (5 miles)
  • Kayaking
    (15 miles)
  • Movie Theater
    (<1 mile)
  • Water Park
    (1 mile)
  • Sailing
    (5 miles)
  • Whitewater Rafting
    (15 miles)
  • Park
    (<1 mile)
  • Winery
    (1 mile)
  • Water Skiing
    (5 miles)
  • Downhill Skiing
    (20 miles)
  • Playground
    (<1 mile)
  • Tennis
    (2 miles)

Other Vacation Rental Amenities
We specialize in groups and families. Rent one or all four cottages for your gathering...all located just a block from downtown Ashland in a unique garden setting from Oak Street to Water Street. Walk to shopping, theaters, restaurants, plays, galleries, park, and skatepark! Children welcome. We have cribs and highchairs available on request.

Reviews for this vacation cottage rental in Ashland, Oregon

Have you been a guest of this property? Write a review!
Jill Thompson

Jill Thompson

San Diego, CA

Great place to stay

June 29, 2013

Beautiful cottage with all amenities. Great location to town

Bonnie Friedman

Bonnie Friedman

Boston, MA

Excellent location, room for everyone

March 1, 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.

Tina Marie Beatty

Tina Marie Beatty

Fresno, CA USA

Our stay at Oak Street Cottage

December 28, 2010

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

Pat Andrews

Pat Andrews

Eureka, CA

Just Right

April 16, 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.

Kelly Rodrigo

Kelly Rodrigo

Long Beach, California

Wonderful Location

September 3, 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

Alice LaMoree

Alice LaMoree

Medford, Oregon

Excellent Accommodations

May 24, 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.

More Information

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Page Views This month: 29 This year: 90 Since listed: 8,623
Last updated: March 17, 2015

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Owner Profile

Constance Dean

Constance Dean


More about the owner
  • School:

    Big Valley High, Modoc High, Big Valley High, 1971, San Francisco State University
  • Work:

    Certified Kitchen and Bath Designer, Inn Manager, Certified Emotion Code Practitioner
  • About:

    I have been the manager and one of the owners of Oak Street Cottages now for 18 years! I love watching these beautiful homes transform your by year to become more comfortable and welcoming for all of our guests, who see the Oak Street Cottages as their " home away from home". My pleasure is to make...
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