Stacy's 2nd St Cottages .. Steps to theaters, Lithia Park and downtown Ashland

Ashland, Oregon

Located downtown in quiet residential area in historic Railroad District . 2 blocks to Shakespeare Festival and 92 acre Lithia park with walking, hiking ,playground and year round Ashland creek.. One block to shopping, dining and Varsity movie theater. Walking distance to Southern Oregon University . Our cottage has 2 bedrooms and 1 bath with double sink. One bedroom has king bed, 2nd bedroom has two twin beds. Kitchen fully equipped. Washer/Dryer, wireless internet, TV with built in DVD Apple TV with Netflix.
Outside area is a beautiful large private courtyard with tables, chairs, propane fire-pit with comfortable seating, propane BBQ. Access to 2 nd street through front courtyard gate entrance. Our property has only one rental. owners have own private outdoor spaces so your outdoor area is never shared. Private off street parking with easy access to back entrance of cottage. Park your car and leave it, easy walking to downtown and theaters. Electric outlet in guest parking area. Free EV charging station in City of Ashland public parking lot one block away. City bus stop across street serves Medford, Jacksonville areas. Owner lives in upstairs apartment
Fully licensed BL00832 PA-2013-01166
Looking to extend your trip to Crater Lake check out our listing vrbo 1368904 for a large home on creek that sleeps 8 all family owned and are managed by grandkids Marie and Shanoah Stanley



  • Downtown


  • Town
  • Mountain View


  • Swimming
  • Cycling
  • Fishing
  • Skiing
  • Golf
  • Mountain Biking
  • Hiking
  • Ice Skating
  • Mountain Climbing
  • Rafting
  • Cross Country Skiing
  • Kayaking
  • Rock Climbing
  • Snowboarding
  • Snowmobiling


  • Not Necessary


  • Antiquing
  • Bird Watching
  • Shopping


  • Fitness Center
  • Hospital
  • Laundromat


  • Museums
  • Winery Tours
  • Health/beauty Spa


  • Cleaned With Disinfectant
  • High-touch Surfaces Cleaned With Disinfectant (like Countertops, Light Switches, Handles, And Faucets)
  • All Towels And Bedding Washed In Hot Water That’s At Least 60ºC/140ºF


  • Enhanced Cleaning Practices


  • Air Conditioning
  • Heating
  • Linens Provided
  • Washing Machine
  • Clothes Dryer
  • Fireplace
  • Parking
  • Internet
  • Towels Provided
  • Wireless Internet
  • Iron & Board
  • Hair Dryer
  • Paper Towels
  • Shampoo
  • Basic Soaps
  • Toilet Paper
  • Living Room


  • Dishwasher
  • Refrigerator
  • Stove
  • Oven
  • Microwave
  • Grill
  • Coffee Maker
  • Toaster
  • Blender
  • Coffee Grinder
  • Ice Maker
  • Pantry Items
  • Dishes & Utensils
  • Kitchen
  • Kettle
  • Dining Table


  • Television
  • DVD Player
  • Smart TV


  • Lawn/Garden
  • Porch/Veranda
  • Deck/Patio
  • Outdoor Furniture
  • Fire Pit


  • Not Suitable For Children
  • Pets Not Allowed
  • Non Smoking Only


  • Historic


  • Dining Area

Dining Checkbox

  • Dining


  • Hospital Contact


  • Deadbolt Lock
  • First Aid Kit
  • Fire Extinguisher
  • Carbon Monoxide Detector
  • Exterior Lighting


  • Emergency Exit Route
  • Fire Station Contact


  • Smoke Detector


  • Police Contact


  • Fenced Yard
  • Desk
  • Desk Chair

Houses Rules

  • 03:00 PM
  • 11:00 AM
  • No parties/events
  • Smoking allowed
  • Pets allowed
  • Children allowed
  • Max occupancy: 4


Cancellation Policy

  • 100% refund if canceled at least 30 days before arrival date.

37 Reviews

    Terrific Location, Comfy Cottage for 4

    5/5 Stayed Oct 10, 2019
    Submitted Oct 13, 2019

    We lucked out, snagging this reservation for the OSF outdoor theater closing weekend. The cottage was clean and comfortable, with a spacious dual-sink bathroom and conveniently equipped kitchen. Stacy was very responsive to questions before and during our visit. The hot tub was fantastic for the crisp, chilly October nights, and the location made it convenient to get to the theaters, downtown restaurants and shops, and the Ashland Co-op. The off street parking made unloading and loading super easy.

    The perfect Ashland cottage

    5/5 Stayed Sep 24, 2019
    Submitted Sep 29, 2019

    Immaculate, comfortable, spacious, very close to theaters, wonderful patio -- who could ask for anything more!

    A lovely stay!

    5/5 Stayed Aug 30, 2019
    Submitted Sep 3, 2019

    The cute little cottage was exactly as described. It was clean, well-equipped, comfortable, and very convenient. I strongly recommend staying here!

    A wonderful place to stay

    5/5 Stayed Aug 20, 2019
    Submitted Aug 27, 2019

    Everything about the property was perfect. Great location lovely home perfect courtyard. We loved the hot tub too. Perfect place for my husband and I plus our two teens. Good base for OSF and the college. Highly recommended.

    Great Getaway

    5/5 Stayed Aug 14, 2019
    Submitted Aug 18, 2019

    Our family had a great time in Ashland at Staceys Cottage. Super cute place, and so close to everything! We walked to the plays every evening. Thoroughly enjoyed our stay! Thank you Stacey, we will be back!

    Wonderful in every way!

    5/5 Stayed Aug 9, 2019
    Submitted Aug 13, 2019

    This is a fantastic place. Very peaceful. Quiet courtyard. Everything you'll need is here! We enjoyed it as a family gathering spot! Well located near everything in town. The owner was helpful and very accommodating. We would definitely go back!

    Cozy and welcoming!

    5/5 Stayed Jul 30, 2019
    Submitted Aug 5, 2019

    Stacy’s cottage was just perfect for a visit to Ashland! Comfortable and great outdoor space! Walking distance to theatres. We plan to stay here every time we go to Ashland!

    Ashland stay

    5/5 Stayed Jul 26, 2019
    Submitted Jul 31, 2019

    Stacy's Cottage was close to everything! We appreciated the short walk to the theater combined with the feel of living in a neighborhood. Her place was clean, quite and comfortable (despite the heat wave we hit (appreciated the A/C). Would definitely book her place again.

    Wonderful stay all around.

    5/5 Stayed Jul 19, 2019
    Submitted Jul 23, 2019

    This is such a wonderful place with a beautiful backyard patio. The house is clean, quiet and conveniently located just a few blocks from the festival , so there is no need for driving and parking downtown since everything you need is in walking distance. We never had the chance to meet our host, but we did meet her mother who lives in the front cottage. She was very friendly and helpful. Looking forward to staying here again the next time we are in Ashland.

    Fabulous spot in Ashland

    5/5 Stayed Jul 13, 2019
    Submitted Jul 21, 2019

    This cottage was perfect for our family of four including two teens. We cooked several meals in the well-equipped kitchen and slept soundly in the comfortable beds. Everything was clean and cozy. And it took under 10 minutes to walk to the Shakespeare festival! Tons of great shops and restaurants within only a few blocks. Can’t beat it!


    5/5 Stayed Jun 14, 2019
    Submitted Jun 19, 2019

    We have been going to Ashland once or twice a year for 25 years now. This is by far the loveliest place we have ever stayed. The courtyard is to die for and the location is perfection.

    A Perfect Place

    5/5 Stayed Apr 11, 2019
    Submitted Apr 18, 2019

    I don't know if I've ever stayed in a vacation rental in which the owner has been as thoughtful in making sure everything would be so perfect for our comfort. And the location couldn't be better. I can't think of think of anything that Stacy could have done better. Thank you for a wonderful time!

    Wonderful stay!

    5/5 Stayed Dec 23, 2018
    Submitted Jan 7, 2019

    We really enjoyed our four days at this spotless and charming home in Ashland over the holidays. The fully stocked kitchen and open kitchen-dining-living room layout was perfect for spending time with family and cooking together. The home is extremely dark and quiet at night, and we loved spending time in the courtyard and hot tub in the evenings. The short walk to town and the co-op make it incredibly easy to enjoy good food. Thank you for everything Stacy!

    Comfortable, quiet, convienant

    5/5 Stayed Oct 19, 2018
    Submitted Oct 22, 2018

    We really enjoyed staying in the cottage, it was quiet, very comfortable, and convienant for all activites in Ashland.

    Perfect place to spend a week doing OSF plays

    5/5 Stayed Sep 17, 2018
    Submitted Sep 25, 2018

    Stacy's cottage is tucked away in a quiet area of Ashland, situated in it's own little piece of heaven. It's an oasis from the hot days with a comfy house, porch and patio to enjoy. The decor is eclectic with a mix of modern and old and adds to the charm of the cottage. The kitchen is well equiped and the place is spotless. We are used to a lot of house rules in VRBO's and a long list of what we need to do when it is time to leave, but not here. A simple load the towels in the clothes washer and that's it! I always like to leave things tidy, though, so did a bit more. If I were to get picky, I would say that a few more smaller serving bowls would have been welcome, but the kitchen has a lot of appliances from the hot water pot to a stick blender. Measuring cups and spoons brought a smile to my face too. While we ate many meals out, we did do a bit of occasional cooking and were able to find what we needed, even some common things likes spices that you need just a pinch of in your favorite recipe. We looked forward to meeting Stacy, but alas, she had a very busy week and that didn't happen. Her mother, Ina, was a delight and I enjoyed my conversations with her as we were leaving the patio for a play or a meal. The large rooms in the cottage gave us plenty of spread out room and the king bed was very comfy. There are twin beds in the other bedroom. Lots of hangers for clothes in both closets. If you are a TV addict, there are just a few channels available on the tv, but there is Netflix included if you are craving a TV fix. We travel to Ashland each year for OSF and will hope that this cottage is available on our next adventure.

    Perfect for our 4-women Ashland getaway!

    5/5 Stayed Sep 13, 2018
    Submitted Sep 16, 2018

    Really good location, within short walking distance of downtown Ashland shopping, restaurants, and Oregon Shakespeare Festival. Our own cottage was very clean, tastefully furnished, quality art on the walls, and complete kitchen with good appliances -- plus courtyard with nice outdoor seating and tables and hot tub (spa). Quiet location, very little street or neighborhood noise. Convenient (reserved) parking. We will definitely choose Stacy's Second Street Cottages for our next visit to Ashland!

    Great location, great place

    5/5 Stayed Sep 4, 2018
    Submitted Sep 9, 2018

    Everything as advertised... although not exactly two blocks to plays, more like 5 minute walk... very close. Pleasant quiet place, full kitchen, air conditioning, and nice water fountain outside the bedroom window. Unfortunately several nights with air quality issues—that’s a problem with living in such a lovely spot, surrounded by forests. By that I mean Ashland and Oregon. Will stay again, I hope!

    Stacy's 2nd St Cottages

    5/5 Stayed Aug 23, 2018
    Submitted Sep 2, 2018

    My husband and I visit Ashland every summer - the draw is the Oregon Shakespeare Theater. But we also love being in Ashland. This is our third year staying at Stacy's Cottages, which is really more of a very comfortable small home. It has everything we need, and if it doesn't, Stacy, Ina and Richard take care of anything special we want right away. Oh, did I mention, the location is amazing . I hesitate to say how much we like it for fear of not being able to get our own reservation. We like to spend 10 -14 days here every summer.

    Comfortable and in a great location!

    5/5 Stayed Jul 31, 2018
    Submitted Aug 4, 2018

    Very nice cottage, with a beautiful private courtyard. Fantastic location, very short walking distance to everything in Ashland. Overall great place!

    Great spot super close to downtown

    5/5 Stayed Jul 22, 2018
    Submitted Jul 26, 2018

    We really enjoyed our stay at the cottage. We visited during fire season and the cottage had everything we needed to escape the smoke. Thanks!

    Best location

    5/5 Stayed Jul 5, 2018
    Submitted Jul 16, 2018

    Comfortable, clean, and all around the best place to stay in Ashland.

    Stacey’s is as comfortable as Ashland itself. You can count on it being the same great vacation.

    5/5 Stayed Jun 27, 2018
    Submitted Jul 7, 2018

    Like coming home. Not much changes in Ashland, especially not Stacey’s. It’s a big part of a special summer week.


    5/5 Stayed Jun 17, 2018
    Submitted Jun 29, 2018

    Everything was perfect! The beds were comfy, the kitchen was very nicely equipped and we love the outdoor garden area. We have been been staying at Stacy's for several years and will be back next year!

    Lovely cottage

    5/5 Stayed Jun 4, 2018
    Submitted Jun 14, 2018

    Immaculate, comfortable cottage in a quiet & convenient location. Thank you Stacy for this wonderful oasis.

    Favorite rental

    5/5 Stayed Sep 16, 2017
    Submitted Sep 24, 2017

    We come to Ashland twice a year and have tried several rentals over the years. Often we're here with my mother and whenever we need a two bedroom home, Stacy's is our favorite. Perfect distance from the Main Street businesses and OSF. Clean, comfortable, quiet and has everything we need. Stacy is a wonderful host and we highly recommend this rental.

    Felt like home

    5/5 Stayed Jul 11, 2017
    Submitted Jul 21, 2017

    Our second time staying at Stacy's and we felt very comfortable and at home. It is cozy, which was good for our group discussions and projects. It is SO conveniently located, perfect for getting to town, plays, the Ashland Food Co op and the bike path.

    Absolutely Outstanding

    5/5 Stayed May 2, 2017
    Submitted May 7, 2017

    Stacy's 2nd Street Cottages are perfectly located and give easy access to just about everything Ashland has to offer. We didn't even need a car. The house is charming and very well maintained, the beds are comfortable with lots of pillows to choose from and the WiFi signal is strong. Stacy stays in the background but if you have questions or any problems she is very responsive (we lost our WiFi signal in a thunder storm and she reset the router within minutes of our call).

    Charming, well-appointed and in a perfect location.

    5/5 Stayed Aug 24, 2016
    Submitted Aug 28, 2016

    This was our eighteenth annual trip to Ashland for the Shakespeare Festival. I think this cottage has become our favorite place to stay. We particularly liked spending time in the garden.

    Very nice - as advertized

    5/5 Stayed May 31, 2016
    Submitted Jun 7, 2016

    The cottage was clean and convenient to the main district. We especially liked spending time out in the patio. We would go there again. Nancy

    The place to stay in Ashland!

    5/5 Stayed Aug 4, 2015
    Submitted Aug 13, 2015

    This is our second time staying at Stacy's 2nd Street Cottage and I almost hesitate to review it because I'm afraid if everyone knows what a great place it is, I won't be able to get future reservations!! Two bedrooms that worked great for us with our two grown sons (twin beds in the second room). The kitchen is fully equipped and I love being able to cook since we need to eat gluten-free. I bring my own toaster because of the gf issue, but otherwise, everything we need is there. Visiting the cats each evening is a nice bonus since we miss ours when traveling. Great access to the theaters and stores - walked everywhere.

    Stacey's Cottages, Asland, OR

    5/5 Stayed Jul 27, 2015
    Submitted Aug 4, 2015

    A second time at Stacey's. Perfect for theater goers and Ashland shoppers. Easy walk from both. Clean and comfortable for two, three or four.

    Simply the best!

    5/5 Stayed May 12, 2015
    Submitted Jun 29, 2015

    We've been going to Ashland for over 15 years, and have stayed in many different locations. We have to say that nothing compares to Stacy's 2nd Street Cottages. Clean, quiet, comfortable accommodations, off-street parking, a beautiful enclosed patio (with 2 sweetheart kitties), 3-10 minutes walking distance to the Food Co-Op, numerous restaurants, shopping, Lithia Park and of course, the OSF theates. A full and well-supplied kitchen, excellent HVAC, TV, DVD, radio, hot tub, and your wonderful hostess, Stacy. We have stayed twice, and are already planning our next trip. We highly recommend!

    What an immaculate, shining jewel!

    5/5 Stayed Sep 15, 2014
    Submitted Sep 24, 2014

    Three of us journeyed back to Ashland to recapture our previous years of fun and enjoyment. We discovered Stacy's 2nd Street Cottages online and perhaps had a bit of trepidation . . . who knows what we might find? Upon arrival we all breathed a sigh of relief -- IMMACULATELY CLEAN, everything works, within 1-3 blocks of literally everything Ashland has to offer -- and there's Stacy. When we couldn't figure out how to get the DVD out of the TV, she was there. The kitchen is full-on, the patio is a lovely place to eat, drink and read books. And even though we didn't use the hot tub, lifting the lid we could see it was as immaculate as the rest of the cottage. The beds and bedding were lovely and comfortable. We would go back -- and highly recommend.


    5/5 Stayed Jun 16, 2014
    Submitted Jun 26, 2014

    We have been traveling to Ashland each year for more than a decade and have enjoyed several types of accommodations. Nothing has compared with our stay at Stacy's 2nd Street Cottage. From our initial booking through our departure, Stacy was the perfect hostess. The cottage was beautifully appointed, the kitchen well stocked with cookware and dishes. Turns out we only ate dinner out twice during our week-long stay as it was easy to cook in due to the available cookware. We also took advantage of the great barbecue grill on the oh-so-comfortable courtyard. When we did dine out some of Ashland's best restaurants (Peerless, Alchemy, Smithfields) are within just a few blocks of the cottage, couldn't have been easier. The OSF is also easily within walking distance. We plan to return to Stacy's and have already recommended her cottage to friends who now have reservations for a week this October. Truly a home-away-from-home experience. Our thanks to Stacy for making this year's Ashland trip an absolute joy!

    Comfy and convenient

    5/5 Stayed Jun 11, 2014
    Submitted Jun 17, 2014

    he location could not be more convenient for theater-going and hanging around downtown Ashland. It's an 8-minute walk to the Oregon Shakespeare Festival's theaters and a 2-block walk to the Ashland Food Coop, where we bought locally raised pork chops and locally caught Rogue River salmon to grill for dinner. The living room/dining room/kitchen are spacious enough, the bedrooms comfortable, the bathroom has two sinks, and the patio a quiet place to relax in nice weather. Stacy, the owner, prefers to stay in the background but she's good about responding to emails and phone calls to make sure everything is as it should be. Just what I want from a vrbo rental.

    Best Cottages in Downtown Ashland!

    5/5 Stayed Apr 24, 2014
    Submitted Apr 28, 2014

    We enjoyed a wonderful weekend in Ashland, thanks to Stacy's accommodations. The location couldn't have been better and the cottage was just what our family needed, with all of the amenities, including a private hot tub! If we needed anything during our stay, Stacy was extremely helpful and responsive. We look forward to our next visit and will definitely tell friends and family to stay here for the perfect vacation!


    5/5 Stayed Feb 18, 2014
    Submitted Feb 25, 2014

    LOCATION, LOCATION, LOCATION. Stacy’s Second St. Cottages has the best of all. Having stayed in many hotels during our visits to Ashland over the past 40-plus years, we are delighted to have discovered this lovely secluded spot with such easy access to any activity we might desire. Just off the main street, in a quiet residential neighborhood, within easy walking distance of all one needs, it provides privacy, peace and tranquility both inside and out. The conversational arrangement of the love seat and sofa around the coffee table in the living room is the perfect spot for planning the day’s adventures over coffee prepared in the fully equipped kitchen, with perhaps some pastries from one of several bakeries within easy walking distance. On chilly mornings the gas fireplace provides a cozy ambiance. Nearby historic Jacksonville provides a lovely outing, as do the many wineries in the surrounding area, should you have a car. Otherwise Lithia Park offers many walking trails as well as various garden areas, a children’s playground and two ponds for leisurely strolling or sitting in the sun or shade. Also nearby is a walking trail just this side of the tracks in the Railroad District, which also has various businesses, including the Food Co-Op, the nearest source of groceries. For those with a car, there is private parking behind the cottage, which is an incredible convenience during the height of the Oregon Shakespeare Festival season. A car is NOT necessary to enjoy Ashland, as all three OSFA theaters, as well as a fine cinema offering first-run quality films, book stores, and a wide variety of boutiques and great restaurants are all within easy walking distance. For relaxation after a full day of activities, the secluded courtyard is a great place to enjoy a glass of wine around the fire pit. A dining table allows for al fresco meals, and the hot tub will relieve any tension from a busy day. The downstairs unit comfortably will accommodate four guests, with two in the king bedroom and two others in the twin room. For a larger group, the upstairs, if available, will accommodate three more, with two in the queen bedroom and one other in the pull-down bed in the living room. The upstairs unit, at an additional cost, has its own large bath and a small kitchen, but its best feature is the lovely deck with a view of the surrounding mountains. Based on several decades of enjoying the delights of the town, we find Stacy’s Second St. Cottages the best.


      Ashland, Oregon

      Rates & Availability

      37 Reviews
      Minimum Stay 2 Nights

      Your dates are Available!


      Includes taxes and fees