In the historic railroad district, walking distance to all the best of Ashland!

Ashland, Oregon

COVID-19 PANDEMIC - please call direct for information on cleaning protocols and further information on cancelation policies 541-821-8925 - cell
Welcome to The Heritage Suite at Second Street Cottages!
The Heritage Suite is located just two blocks from the center of Ashland, including the Oregon Shakespeare Festival theaters, delightful shops, and unique restaurants.

It is one of two separate suites at Second Street Cottages: a turn-of-the-century home now completely renovated as a travelers' accommodation. It is located on a lovely, quiet residential street in the historic Railroad District. We welcome guests to spacious, fresh rooms and wonderful outdoor spaces.

The Heritage Suite:
- 4 bedrooms, 3 full bathrooms (sleeps up to 8 people)
Consisting of:
* Two bedrooms with private baths and queen beds, and
* Two bedrooms with twin beds and a shared bath
- Living room, dining area
- Large, fully-equipped kitchen
- Oversized front porch and patio

The Heritage Suite has all the amenities: spacious rooms, hardwood floors, finely-appointed furnishings, TV/DVD player, free WiFi, and central air/heat.

The Heritage Suite has its own private entrance, an oversized front porch with table and chairs (seats 6) for outdoor dining – as well as casual sitting area for enjoying coffee, drinks, or just relaxing.

Please note there are security cameras on the exterior of the property.

Second Street Cottages also has a charming 2 bedroom/2 full bathroom unit: The Garden Suite. It can be seen at VRBO listing # 737950. Although the two suites are independent units, they can be rented together at the same time (depending upon availability). Please call for availability of a one night reservation. We are happy to accommodate if possible.



  • Fishing
  • Golf
  • Cycling
  • Basketball Court
  • Sailing
  • Hiking
  • Skiing
  • Cross Country Skiing
  • Ice Skating
  • Mountain Biking
  • Kayaking
  • Rock Climbing
  • Rafting
  • Golf Privileges Optional
  • Snowboarding


  • Fitness Center
  • Hospital


  • Museums
  • Winery Tours
  • Health/beauty Spa


  • Cleaned With Disinfectant
  • Check In And Check Out With No Person-to-person Contact
  • Minimum 1-day Vacancy Between Guest Stays
  • 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


  • Antiquing
  • Bird Watching
  • Sledding
  • Wildlife Viewing
  • Shopping
  • Boating
  • Water Sports


  • Not Necessary


  • Enhanced Cleaning Practices


  • Downtown


  • Property Has Guest Safety Measures


  • Coffee Grinder
  • Microwave
  • Coffee Maker
  • Pantry Items
  • Dishwasher
  • Dishes & Utensils
  • Kitchen
  • Stove
  • Kettle
  • Dishes & Utensils For Kids
  • Oven
  • Refrigerator
  • Blender
  • Toaster


  • Historic
  • Family

Suitability Chkbox

  • Minimum Age Limit For Renters


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


  • Pets Not Allowed
  • Wheelchair Inaccessible
  • Children Welcome
  • Non Smoking Only


  • Fire Station Contact
  • Emergency Exit Route


  • Games
  • Books
  • Television
  • Satellite/Cable
  • Video Library
  • DVD Player


  • Police Contact


  • Smoke Detector


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


  • Outdoor Furniture
  • Tennis
  • Golf
  • Deck/Patio
  • Ski & Snowboard
  • Lawn/Garden
  • Porch/Veranda

Dining Checkbox

  • Dining


  • Hospital Contact


  • Dining Area

Houses Rules

  • 04:00 PM
  • 11:00 AM
  • No parties/events
  • Smoking allowed
  • Pets allowed
  • Children allowed
  • Max occupancy: 8

Fees and charges are established based on occupancy. Additional charges will apply for any additional guests staying at the property (incl. children).

Cancellation Policy

  • 100% refund if canceled at least 14 days before arrival date.

96 Reviews

    Such a great location

    5/5 Stayed Jun 11, 2021
    Submitted Jun 15, 2021

    The house is great, such a nice location. We have two small kids (1yr and 3yr) and this house accommodates us nicely. Thoughtful things like child locks on the door to outside and a level, fenced front yard. Our ONLY qualm is the wood floor. It’s extremely old with some exposed nails and splintering wood. You really have to wear house slippers or shoes so you don’t get snagged or get a splinter (which we did!)

    Family reunion

    5/5 Stayed May 28, 2021
    Submitted Jun 1, 2021

    Perfect location, lovely front porch Upstairs got a little hot without air conditioning Overall great place otherwise

    Family COVID Reunion

    5/5 Stayed May 21, 2021
    Submitted May 25, 2021

    The property is exactly as photos shown. It is the best home away from home. Plenty of rooms to accommodate 6 of us, and the kitchen is fully stocked with cups, plates, cooking utensils, coffee maker.... making meal in the kitchen is as convenient as at home. We had an afternoon tea on the front porch, and It was the best treat for all of us, after days of outdoor activities. Thank you for the wonderful and delightful accommodation, this would be a very memorable trip for all of us.

    Excellent, very clean stay

    5/5 Stayed May 14, 2021
    Submitted May 18, 2021

    We had a minor problem and I couldn't believe how quickly Sugar came over to help. The house was spotless -- even my mom was impressed which is saying something! It could not have been better located, either -- just 1.5 blocks, I think, from the main drag but SILENT at night (how is that possible?). Anyway we had zero complaints. Thanks Sugar!

    Cute cottage right in the heart of Ashland!

    5/5 Stayed Feb 16, 2021
    Submitted Feb 20, 2021

    Super cute cottage. Walking distance to Ashland’s Main Street with shopping, restaurants and Lithia park! We had a great time walking around Ashland. The home was clean and had everything we needed for our stay. I would definitely stay here again!

    Quaint cottage and town

    5/5 Stayed Jul 26, 2020
    Submitted Aug 10, 2020

    My family and I came to Ashland, Oregon on a whim and I couldn’t have picked a better place to stay. The cottage was so quaint, clean, plenty of room, wonderful porch to have breakfast/lunch/dinner on, a front yard for the kids to run around in, wonderful location and walking distance to so many stores and shops. Hidden restaurants on side streets between houses you’d never guess were there. Sugar is fantastic! She’s easy to get a hold of, has made sure everything you need is there, and has a heart of gold! We are so happy with our experience and can’t wait to come back!

    Comfortable, well equipped, and central location

    5/5 Stayed Nov 25, 2019
    Submitted Dec 3, 2019

    This was a great spot for a family get-together for Thanksgiving. Close walking distance to downtown restaurants, Lithia Park, etc. Sugar (the owner) was very kind to stop by with a lantern as a wind storm was knocking out power in some parts of town (luckily didn't affect us). Only quibble might be a somewhat slow internet connection, which for this time didn't matter, but if needing to get some work done, that could use a speed bump.

    Wonderful, charming property a few steps from downtown Ashland

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

    House was absolutely lovely. Was spotless, well equipped and very very charming. Beds were comfortable and home contained everything you needed to feel very much at home. Location was excellent, an easy walk to all attractions. I came with 2 girlfriends and we LOVED it. We hope to return next year.

    Great location

    5/5 Stayed Oct 19, 2019
    Submitted Oct 21, 2019

    We loved our stay here. Very clean, very convenient, fit our needs.

    Terrific home in Ashland for a group

    5/5 Stayed Oct 7, 2019
    Submitted Oct 12, 2019

    We have stayed in Sugar's house numerous times and have enjoyed every time. It is a terrific base in Ashland for a group of six adults. The kitchen is well stocked, the location couldn't be beat and the front porch caps it all off. Sugar is an excellent hostess. We highly recommend this house.

    Great Stay in Ashland

    5/5 Stayed Oct 1, 2019
    Submitted Oct 3, 2019

    Lovely home and so convenient for everything in downtown Ashland. Nice not to have to figure out where to park, all around theater and restaurants are walkable.

    Location, location, location

    5/5 Stayed Sep 2, 2019
    Submitted Sep 7, 2019

    Great location. Walking distance to all that downtown Ashland has to offer. 0.3 mi to OSF. Great front porch for sitting and relaxing.

    Beautiful little cottage

    5/5 Stayed Aug 19, 2019
    Submitted Sep 3, 2019

    This is a beautiful little cottage and very comfortable. A very nice, functional kitchen as well. We really enjoyed sitting on the front porch in the evening.

    2nd Street

    5/5 Stayed Aug 12, 2019
    Submitted Aug 19, 2019

    Wonderful location & well appointed cottage—everything we needed for a pleasant & comfortable week

    Like home

    5/5 Stayed Jul 31, 2019
    Submitted Aug 4, 2019

    Have stayed for several years. Great experience.

    Our Home in Ashland

    5/5 Stayed Jul 25, 2019
    Submitted Jul 30, 2019

    We love staying at the Heritage House.

    Charming and lovely! Felt like home. Close to theaters. Perfect for us!

    5/5 Stayed Jul 16, 2019
    Submitted Jul 21, 2019

    Easy communication with Sugar, thoughtful touches, all the amenities we wanted. We’ll be looking to stay here again next year.

    Perfect porch, best location

    5/5 Stayed Jun 28, 2019
    Submitted Jul 2, 2019

    We had a great time here! Close walking distance to downtown, stores, restaurants, ect. Great food and friendly people in Ashland, we spent a lot of time sitting outside and enjoying the great front porch. Couldn’t be happier with our stay.

    Another great visit

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

    This is our third visit to this house (maybe fourth, I forget). It is comfortable and convenient. We go to Ashland for the theater, but what we enjoy is time with our family and friends. The front porch is conducive to that. We order pizza, get take out from Market of Choice, and cook easy dinners, and then eat on porch, while those walking by look on with envy.

    Good Base for OSF

    5/5 Stayed Jun 17, 2019
    Submitted Jun 20, 2019

    Enjoyed our time in Ashland.

    Beyond expectations

    5/5 Stayed Jun 6, 2019
    Submitted Jun 22, 2019

    The best for our family needs!

    Ashland regulars

    5/5 Stayed Jun 4, 2019
    Submitted Jun 9, 2019

    This is the second time that we've stayed at Sugar's property and we've greatly enjoyed it both times. Everything works and though the dining table is a bit small we were able to eat on the front porch each meal which was delightful.

    Cosy cottage in Ashland

    5/5 Stayed May 10, 2019
    Submitted May 12, 2019

    Well supplied charming cottage walking distance to all Ashland theatres and shops and restaurants.

    We found the perfect place for us

    5/5 Stayed May 2, 2019
    Submitted May 6, 2019

    My sisters and I have a yearly reunion in Ashland and have tried various rentals. We will be coming back here each year from now on. It has everything we need and want. Lovely front porch for appetizers and meals. Fully stocked kitchen, close to theaters but in a quiet neighborhood and comfy beds. Thank you Sugar!

    Wonderful property

    5/5 Stayed Apr 25, 2019
    Submitted May 1, 2019

    I've stayed here on several trips to Ashland and have nothing but superlatives. The location is perfect - theatre, restaurants, shopping, groceries are all easily walkable. The house is bright, the furnishings are comfortable, and the porch is great when the weather permits. I've stayed here with a group of women. This last visit we had three couples. Next time we'll have four couples. And in all cases the house worked really well for us. Sugar is a lovely host. Communications are all clear and pleasant. You cannot go wrong staying here!

    Wonderful home!

    5/5 Stayed Dec 21, 2018
    Submitted Dec 28, 2018

    We had a large family gathering in Ashland for Christmas. This house was perfect for all of us. Sugar provided so many extra touches, including a Christmas tree and Christmas decorations. It made everyone feel at home. The kitchen was well stocked. There were enough plates for all of us and there were good knives for preparing the food. Thank you for providing our home away from home.

    Very nice house in great location

    5/5 Stayed Oct 15, 2018
    Submitted Oct 23, 2018

    Our visit to Ashland was outstanding, as usual. Sugar's house is equipped, very comfortable for 6 adults, and an easy walk to the restaurants, shops and The Oregon Shakespeare theaters in town.

    flawless - would return

    5/5 Stayed Sep 25, 2018
    Submitted Oct 6, 2018

    nice usable porch, good beds, clean, well supplied.

    Great Place

    5/5 Stayed Sep 10, 2018
    Submitted Sep 17, 2018

    Wonderful experience


    5/5 Stayed Sep 5, 2018
    Submitted Sep 10, 2018

    Lovely house, well equipped, close to everything


    5/5 Stayed Aug 30, 2018
    Submitted Sep 3, 2018

    This is our second year. We plan to return again next year. It’s very clean and comfortable, has a great covered porch and is a short walk from the shops and theatre. We really enjoyed our stay.

    Great house in a great location!

    5/5 Stayed Aug 6, 2018
    Submitted Aug 9, 2018

    Beautiful spot with all the comforts of home, within walking distance to theater, restaurants and shops!


    5/5 Stayed Aug 1, 2018
    Submitted Aug 8, 2018

    Our group has stayed here for several years and like everything about the property and it’s location.

    Our HomeAway Again

    5/5 Stayed Jul 26, 2018
    Submitted Jul 31, 2018

    We love staying in the cottage every July. The smoke was pretty bad this year but we were fine when we were inside. Outdoor evening plays were canceled leaving us more time in the house. Thanks for keeping it so lovely for us each year.

    Clean, comfortable, close to everything we needed

    5/5 Stayed Jul 20, 2018
    Submitted Jul 26, 2018

    Always a great place to stay. Walk to town and theaters in minutes. Love the comfy front porch! Owner knows how to do it right.

    Terrific place to stay in Ashland

    5/5 Stayed Jul 12, 2018
    Submitted Jul 22, 2018

    This house is just wonderful! Every room is beautifully decorated and very comfortable. The kitchen is completely stocked even down to the saran wrap (which I forgot to buy). We were there during rather extreme heat (103) and the air conditioning worked perfectly. It's about 3 blocks from the theaters, and only 1.5 blocks from the ice cream parlor. It's such a great house that we have already booked a stay there for next year.

    Great location. Well maintained. Sugar very nice and responsive.

    5/5 Stayed Jul 2, 2018
    Submitted Jul 12, 2018


    Great family stay -- year after year

    5/5 Stayed Jun 29, 2018
    Submitted Jul 7, 2018

    2018 was our 25th annual family trip to Ashland, and our second year here, having discovered it in 2017. Truly one of great front porches in Ashland -- convenient for eating, reading, people watching, and catching up with our family that now spans three west coast states. The theaters and downtown are convenient, but the best part of the trip is just hanging out with family at a comfortable place. Skip the restaurants; get take out from Market of Choice; avoid the crowds; and relax.

    Perfect for a small group

    5/5 Stayed Jun 26, 2018
    Submitted Jul 1, 2018

    This was our 5th stay at the cottage and we hope to add many more to that number. Clean, cozy, close to the main streets of Ashland. If a rental cottage is what you're after then this is it.

    Strong Recommendation

    4/5 Stayed Jun 6, 2018
    Submitted Jun 14, 2018

    A great house, well supplied, great location. Comfortable, clean etc. we would strongly recommend this property and we have stayed in Ashland at many diff. places

    Great family stay in Ashland

    5/5 Stayed Jun 1, 2018
    Submitted Jun 7, 2018

    This is our second year to stay at Heritage House for our annual family get together.The house is spotless and comfortable, has a fabulous front porch, and the best location we have ever found. The opportunity to meet our host this time made it even better. We plan to be back every year!

    Almost Like Home

    5/5 Stayed May 29, 2018
    Submitted Jun 4, 2018

    We look forward every year to returning to “The Cottage”. The year we missed out on making reservations quick enough...we almost didn’t go to OSF. We found another option...but all we did was lament over how much better it would be at The Cottage. When we’re there...we feel at home...

    As always, a wonderful time

    5/5 Stayed May 10, 2018
    Submitted May 17, 2018

    This is the second time our group of friends has stayed at this property, and this time we also stayed at the Hideaway property located behind this one. Cozy, conveniently close to OSF, and thoughtfully set up, this is a great place for a group to stay while watching some wonderful performances. A chance of sighting deer in the early morning.

    Cheerful and cosy

    5/5 Stayed May 4, 2018
    Submitted May 7, 2018

    House was clean, cheerful, sunny, welcoming. Owner came to meet us personally and left a nice card to welcome us. We had a great time. All needs met.

    Great place to stay

    5/5 Stayed Mar 28, 2018
    Submitted Apr 10, 2018

    Have rented multiple houses in Ashland for the Shakespeare festival. This was the best! Close to the theater, close to the co op. Great places to eat near by.


    5/5 Stayed Mar 23, 2018
    Submitted Mar 26, 2018

    Everything was lovely! The location was perfect for walks, parks, theater, restaurants. The kitchen was well/appointed. Beds were comfortable. Sugar was very gracious, welcoming and thorough without impinging. Our only issue was the dining table only had room for 4

    Lovely cottage in Ashland

    5/5 Stayed Mar 9, 2018
    Submitted Mar 12, 2018

    We thoroughly enjoyed our stay here, 6 women, plenty of comfortable beds and three bathrooms, perfect! Only two blocks to Ashland's Main St and 4 blocks to the theaters. Very quiet despite being so close to Main St.

    Great place for our family

    5/5 Stayed Dec 23, 2017
    Submitted Dec 26, 2017

    This is a cozy little cottage with 4 bedrooms and so convenient to downtown, shops, and the center of the theater district. Everything seems to be close by. Sugar was very responsive to any questions we had. Absolutely no reservations recommmending this property.

    Great house in a wonderful community

    5/5 Stayed Oct 16, 2017
    Submitted Oct 21, 2017

    This is a terrific, well appointed house professionally managed. For the theaters and restaurants, it couldn't be in a better location.


    5/5 Stayed Sep 27, 2017
    Submitted Oct 20, 2017

    We have stayed here several times. It's a great location, and always in good shape. We've never had to call to have anything adjusted. The process to check in and check out is so easy. In a way, I wish I had a reason to meet Sugar, but we haven't needed to. We love the Keurig coffee that is provided too. We can really just check in after a long drive and relax that we are comfortably at our temporary home. Lots of charm and lots of comfort. We look forward to our next visit.

    Continues to be a great place to stay in Ashland

    5/5 Stayed Sep 22, 2017
    Submitted Sep 29, 2017

    Clean, comfortable accommodation. Close to everything, convenient to town, festival venues.


    5/5 Stayed Sep 10, 2017
    Submitted Sep 17, 2017

    This four bedroom / three bath home was perfect for me and three friends. We senior women travel to a different location each year. Rarely have we found a location and home so perfect! The Home owner's careful attention to detail is evident and wonderful.

    Perfect for an Ashland week-end.

    5/5 Stayed Aug 31, 2017
    Submitted Sep 15, 2017

    We rented the house for the first time this year. We liked it so much we've already booked for 2018. It's in a perfect location for the plays and is clean, comfortable and has a wonderful front porch that's perfect for an afternoon for cribbage.


    5/5 Stayed Aug 2, 2017
    Submitted Aug 6, 2017

    Great place to stay.

    "OUR" Home away

    5/5 Stayed Jul 27, 2017
    Submitted Aug 17, 2017

    We come to Ashland every year and stay at this location. It feels like our own home. We love the convenience of the location and the familiarity after so many years.

    Perfect for our annual family get together

    5/5 Stayed Jul 21, 2017
    Submitted Aug 1, 2017

    This was our 25th year coming to Ashland. Sometimes it has been as few as three people; once we had twelve. This year it was us and two daughters. (One daughter and our son-in-law had to drop out at the last minute.) But this home was perfect for us. It was convenient to the theater and the Coop. The kitchen was small but very well equipped. And the porch was great for eating and just hanging out. We would definitely stay here again.

    Family Shakespeare trip

    5/5 Stayed Jul 11, 2017
    Submitted Jul 17, 2017

    Six of us (2 couples, two singles) stayed six days in this lovely home. Comfortable accommodations, close to downtown and within walking distance to plays, restaurants, etc. Kitchen was well equipped, bedrooms & bathrooms comfortable. Great front porch for hanging out and watching the world go by. Two things could have made it better - there's no place inside for everyone to sit down together for a meal. The table on the porch will accommodate six, if you bring chairs from the kitchen, but the table is so big, it's hard to manuver around. But, we figured it out and had a great time.

    A+ porch sitting

    5/5 Stayed Jun 30, 2017
    Submitted Jul 6, 2017

    Thanks Sugar, for loaning us your wonderful home. We enjoyed the porch, the lawn, the very comfortable beds. It was so close to everything, we just walked.

    Great Accommodations, VRBO ruined whole experience

    5/5 Stayed Jun 26, 2017
    Submitted Jul 9, 2017

    Sugar Mejia is an excellent owner, Heritage Cottage is well maintained and is an outstanding house. BUT, dealing with VRBO will keep us from returning. You cannot be reached with concerns. Bills come without explanation, are paid, then at the last minute $271 was added, again without explanation. I have come away feeling cheated as we seem to have paid far more than the rate quoted plus taxes and cleaning fee. I can't prove a thing, as you provide no way for me to find out what was happening. At no time did I find out details of the billing. How you get by with this is a mystery to me. Just know Sugar will lose a client because of VRBO. I have stayed in one of Sugar's two second street cottages every year since 2013 and have shared them with family and friends. We will miss our annual trips. Fortunately, we have many choices available for our future visits not involving VRBO

    The perfect Ashland vacation lodging!

    5/5 Stayed Jun 21, 2017
    Submitted Jul 6, 2017

    A cozy and welcoming cottage! The bedrooms are well-separated from one another, and it is wonderful having three full bathrooms! Comfortable, very close to the theaters, a great socializing spot on the front porch and well-equipped with everything that you might need.

    Charming vacation home

    4/5 Stayed Jun 2, 2017
    Submitted Jun 15, 2017

    The vacation home on Second St. is in a perfect location for visiting Ashland. It is an easy walk to shopping, restaurants and the theaters. Our favorite part of the house was the large and accommodating front porch. Everything was great for our annual family visit. We will be coming back again next year.

    Fantastic Home and Location

    5/5 Stayed May 26, 2017
    Submitted Jun 8, 2017

    A beautiful home with great proximity to downtown Ashland. We loved the front porch in particular. It was a nice place to enjoy breakfast or wind down in the evening. The home is near a busy street, but the noise is not that noticeable outside and not noticeable at all inside. Plenty of parking. Cute decor.

    Best of Ashland

    5/5 Stayed May 24, 2017
    Submitted Jun 6, 2017

    We've been staying here for over 10 years and absolutely love it!

    Charming, clean and great location

    5/5 Stayed May 9, 2017
    Submitted May 12, 2017

    This was our third visit to the 2nd Street Cottages, and we will hopefully return again. A perfect place for a girls getaway.

    comfortable home close to downtown

    5/5 Stayed Mar 30, 2017
    Submitted Apr 13, 2017

    we had a great time

    Lovely place.

    5/5 Stayed Dec 23, 2016
    Submitted Jan 11, 2017

    Smaller than it appears in the ad but comfortably sleeps eight (four in twin beds). Nice kitchen with small dining area and living room. Nicely appointed and an easy walk to theaters and restaurants. Will stay again.

    Charming, perfectly situated house.

    5/5 Stayed Nov 22, 2016
    Submitted Dec 6, 2016

    Absolutely everything about this house was as advertised: it is attractive, comfortable, has all the amenities, and is located conveniently to downtown Ashland. Sugar was efficient and a pleasure to deal with. Our extended family of 7 could not have been more pleased.

    Lovely, Cozy Cottage

    5/5 Stayed Oct 29, 2016
    Submitted Nov 2, 2016

    Six of us stayed at the 2nd Street Cottages October 29th and 30th to celebrate a family member's birthday. It was perfect! The cottage had a well appointed kitchen where we cooked breakfast and a dinner with everything we needed. The Keurig coffee maker was nice, with a selection of coffee to suit everyone's taste, along with an assortment of teas. The bedrooms are beautifully decorated, with comfortable beds and linens. The cottage was clean and cozy, and we even managed to enjoy the beautiful covered porch despite some rain! The location is quiet and conveniently located just blocks from the theaters and restaurants. We loved having Sunday brunch at Larks which is located in the Ashland Springs Hotel. The food and service were spectacular! We enjoyed Lithia Park in all its fall glory, although I suspect it's beautiful any time of year! I highly recommend the 2nd Street Cottages and look forward to a return visit one day.

    A Delightful House

    5/5 Stayed Oct 17, 2016
    Submitted Nov 1, 2016

    Four women friends stayed at this house for a week. We were very happy with it. It is very clean. It is well supplied with dishes, pots and pans, silverware and utensils, everything you need when you rent a house. We ate many meals at the house so saved some money by eating in. There is a large screen TV and internet capability. I recommend this house!

    Perfect Ashland cottage

    5/5 Stayed Oct 15, 2016
    Submitted Oct 17, 2016

    We loved everything about this cottage! Great neighborhood, beautifully decorated with attention to detail, clean & has everything you could need. Great layout to bring us all together yet enough bedrooms and bathrooms to give us all our own space. The owner knew my sisters and I were treating our mom for her birthday and had flowers and balloons waiting. She also expedited the cleaning after the previous guests checked out so we could check in early since we arrived during a storm. She really knows how to make her guests stay perfect! We all felt spoiled & will return.

    We return often

    5/5 Stayed Oct 10, 2016
    Submitted Oct 18, 2016

    Very clean place and great location. Well equipped, and as described on VRBO. Helpful owner. Close to theater, Lithia Park and great restaurants.

    I'll keep coming back.

    5/5 Stayed Oct 6, 2016
    Submitted Oct 22, 2016

    Just did a repeat stay in this property and loved it all over again. The location is amazing, only about 1 1/2 block from Main Street. Just park the car and enjoy all that Ashland has to offer. The home is well appointed and comfortable. 4 bedrooms and 3 baths worked well for 4 guests. October weather was fabulous so we were able to enjoy the lovely front porch. Looking forward to my next stay in this home.

    A wonderful property, perfect location, and a place to return another time.

    5/5 Stayed Sep 27, 2016
    Submitted Oct 14, 2016

    Second Street Cottage, Heritage Suite, was perfect for our group of 5 college friends. The house is attractively decorated, very clean; the beds are comfortable, the kitchen is very well equipped. The front porch has two nice sitting areas and the house feels secure with its new picket fence that surrounds the front of the property. A perfect location in Ashland. An easy walk to the OSF theatres, restaurants, galleries, and grocery store. The owner couldn't be nicer or more accommodating. A wonderful property.

    Comfortable, great location, the best front porch in town for relaxing with friends.

    4/5 Stayed Sep 19, 2016
    Submitted Sep 29, 2016

    We enjoyed our stay (group of 5 adults) and when the coffee maker failed, Sugar was prompt with a replacement. Wi-fi was spotty at times, but always recovered. All in all, a great place we have enjoyed for several years.


    5/5 Stayed Sep 9, 2016
    Submitted Sep 12, 2016

    We thoroughly enjoyed our stay at the 2nd street cottage. It was within walking distance of the Festival and some great restaurants. The house is well furnished and immaculate - fluffy towels - just what you need in the kitchen - and even interesting books to read. We look forward to our next visit.

    Enjoyable house, great location for plays and restaurants

    5/5 Stayed Sep 7, 2016
    Submitted Sep 16, 2016

    We were four adults who came to see the plays in Ashland. This house was convenient and comfortable. No complaints at all. We loved how close it was theaters, Main Street, Ashland Co-op, and great parking.

    Clean, well-furnished attached cottage, with a caring host in a great location

    5/5 Stayed Sep 1, 2016
    Submitted Sep 16, 2016

    This was our second year in a row staying in Sugar's 2 story, 4br/3bath (which we use as 3 br) cottage, and won't be our last. We come out to Ashland to indulge in the plays of the Oregon Shakespeare Festival, and the enjoyable ambiance and great eating of Ashland. The cottage is located just off of the main downtown streets but is on a quiet block of well-kept homes and a church whose adjacent parking lot can be used for easy off-street parking, although we've never had trouble getting on-street parking as well. The reality is we rarely use the cars while there as the theatre, the Coop for groceries, the liquor and wine stores, the hardware store, the bookstore, the restaurants, the drugstore, etc. are all just a few blocks away. The cottage is setback from the street with a full-width covered front porch with table and chairs to enjoy sitting outside. With the two bedrooms with private baths separated from each other on the ground floor, and two bedrooms with a bath upstairs, there is great privacy for each of the couples. The place is spotlessly clean and well-equipted, and well maintained. Sugar checks in to see that all is fine, and she responds immediately to any concerns. A great experience.

    Great lodgings!

    4/5 Stayed Aug 27, 2016
    Submitted Aug 30, 2016

    The Suite is a clean, comfortable, convenient place for a visit to Ashland. Current owner is doing a great job of keeping it up. Noticed some nice improvements on our 2016 visit. Everything is in good working order. So close to town and Festival venue, while still being in a nice neighborhood. Will continue to book our family annual trip in 2nd Street Cottages.

    Good location and comfortable living space.

    5/5 Stayed Aug 3, 2016
    Submitted Aug 7, 2016

    We really like the neighborhood feeling and the easy walk to every place.

    Lovely home, wonderfully located

    5/5 Stayed Jul 12, 2016
    Submitted Jul 20, 2016

    Our extended family of 7 very much enjoyed making this our Ashland home for five nights while attending the Shakespeare Festival. The home and kitchen were very well equipped -- we cooked all but two meals in -- comfortable and welcoming. And the location couldn't be better! We would definitely stay here again if we needed four bedrooms.

    Comfortable and well-maintained.

    4/5 Stayed Jul 3, 2016
    Submitted Jul 14, 2016

    The location was perfect -- an easy walk to theaters, the main street, and the railroad district. The kitchen was very well stocked for any kind of cooking and eating and the front porch was perfect -- comfortable and full of chairs. We had a party of 8 staying at the house, with enough beds for all of us. The bedrooms upstairs (2 twins each) would have been uncomfortable if the weather had been hot. The heat rose and the air conditioning was inadequate. Fortunately, our week was very cool. The main floor was thoroughly comfortable. The house is listed as suitable for 8 and we all had places to sleep. The 8 of us really could not fit at the kitchen table, though, and the house became less perfect when more than 4 people stayed there. (I also was surprised to learn that the listing price was only for 4 and that each additional person had to pay extra-- per night.)

    A Special Cottage in Ashland

    5/5 Stayed Jun 27, 2016
    Submitted Jul 6, 2016

    This was my 4th visit to Second Street Cottages, my first since Sugar Mejia became the owner. All was very fine last year, but this year Heritage Suite was amazing! We are four single, older women who have enjoyed the cottage because of its comfort, its privacy and its convenience to downtown and the theaters. Sugar has put in vast amounts of money, time, effort and creativity to make our stay even more delightful than before. The new appliances, the additions in the bathroom, such as necessary grab bars, the new, comfortable furniture all enhanced the cottage. She has put new outdoor furniture on the porch, inviting one to read and relax outside.The box of goodies on the kitchen counter, the well-stocked cupboards, and the candies placed on the bedside tables, all added to our special delight. My niece, her husband and daughter were in Orchard Suite at the same time. Sugar made them very welcome, as they arrived early by plane and she solved the problem of their luggage having to be stored until their suite was available. She visited with them, gave them glasses of wine and made their first visit to Ashland begin memorably. She's a warm, gracious, charming hostess who instantly makes guests welcome and her friends. We have every intention of returning next summer to enjoy theater and our special cottage in Ashland. Thank you!

    Great house with ample space. We all 4 had our own room.

    5/5 Stayed Jun 6, 2016
    Submitted Jun 14, 2016

    Great location. Love the porch.

    Great Place for a Family

    4/5 Stayed May 27, 2016
    Submitted Jun 1, 2016

    The house is located right in the heart of Ashland, easy access to everything downtown. Great layout and perfect amenities for you and the family. It was also extremely clean and well maintained..... Very classy place. The owner was easy to get a hold of and answered all of our questions and concerns within a matter of minutes. I would definitely recommend this house for two families.

    Charming and quaint

    5/5 Stayed May 22, 2016
    Submitted May 29, 2016

    We five senior ladies have rented the same cottage twice and find it very clean, ample in space, and the beds comfortable. The location is great for shopping, dining, and an easy walk to the Shakespeare Theater. The front porch is perfect for a cool drink and socializing. Parking is ample and the neighborhood is safe and quiet. What's not to like? .

    5+ years and still enjoying it

    5/5 Stayed May 20, 2016
    Submitted May 25, 2016

    We've been going to the Cottage for more than 5 years (spring and fall) and and think of it as a second home in Ashland. Everything about it is just right!

    A cozy cottage and incredible host

    5/5 Stayed May 11, 2016
    Submitted May 27, 2016

    Our stay at Second Street Cottages met all of our expectations. It has all the comforts of home and is meticulously maintained. It is also close to the theaters and excellent restaurants. It is also within a few blocks of The Co-Op, a Whole Foods type of store and cafe. Our host, Sugar, is a gem. She is very responsive, hospitable and gracious. We plan to make this our Ashland home when we return next year. Thank you, Sugar, for everything. Dale and friends

    Really nice place

    5/5 Stayed May 1, 2016
    Submitted May 11, 2016

    We had a great time at the Heritage House in Ashland with our extended group. Everyone was comfortable and happy with the location and the set up. The porch is especially nice, kitchen well supplied and the bedrooms all comfortable, clean and private enough that we did not feel squeezed. Highly recommend and look forward to returning.

    It was a beautiful place to stay, so close to downtown. Everything is within walking distance.

    5/5 Stayed Apr 13, 2016
    Submitted Apr 28, 2016

    Second Street cottages are beautifully decorated & incredibly clean. My whole knitting group was comfortable. We had places to sit & knit and chat. We cooked together. Sugar was so available and helpful. It was just a wonderful experience. When we come back, we're definitely staying there again.

    Great Thanksgiving

    5/5 Stayed Nov 24, 2015
    Submitted Nov 29, 2015

    We spent 4 days here during Thanksgiving week while visiting our son who attends SOU. This was a wonderful house to celebrate a holiday in; a kitchen with far more (good!) supplies than I have ever seen in a VRBO home, a quiet peaceful place steps from downtown and Lithia Park, and a cozy relaxing house. The beds were comfortable, there were more than adequate supplies for our time there, and the extras provided were thoughtful - we even had a seasonal Welcome basket. We walked almost everywhere we needed - and had a dedicated parking spot for the times we did not. While a bit pricey for this time of year, this house was an excellent find; would definitely recommend it.

    Perfect family vacation house walking distance to Lithia Park!

    5/5 Stayed Oct 30, 2015
    Submitted Nov 2, 2015

    I've done VRBOs all over, and this was one of the best I've ever stayed in (the pictures don't even do it justice, in fact). 4 bedrooms, lots of beds for kids (they can stay upstairs), 2 big bedrooms for adults downstairs, 3 bathrooms with showers, nice wood floors, and even a Halloween goody basket and fruit, soda, etc. left for us (and coffee with coffeemaker etc.). And the location is perfect, quiet but very close to the main drag. An easy walk with the family to Lithia Park. And Sugar, the owner, was gracious and responsive and generous. I plan to stay here every time I go to Ashland (we have family here) if it's available. And I DEFINITELY recommend it for Halloween weekend in particular (Sugar gave great recommendations for activities).

    Heritage House

    5/5 Stayed Oct 4, 2015
    Submitted Oct 14, 2015

    A group of 7 senior ladies spent a wonderful 4 nights at this house. The kitchen was well furnished as was the rest of the house. There are 2 queen beds and 2 bathrooms on the main floor and 4 twin beds and one bathroom on the 2nd floor. We found the house very comfortable and near all the downtown area so we could walk everywhere. There is a wonderful coop grocery 1/12 blocks from the house.

    Great Location, Charming Cottage

    5/5 Stayed Sep 29, 2015
    Submitted Oct 6, 2015

    We stayed with another couple for 4 days for the the Shakespeare Festival and had a wonderful time! This cottage was immaculately clean and had everything we could possibly need to enjoy our stay. Afternoons on the porch with a glass of wine, easy walking distance to anything in Ashland, comfortable beds, central air conditioning, and excellent parking. Sugar was the best! Great communication. We forgot a wrist watch there and she promptly contacted us and arranged to mail it back. Thank You--We'll definitely be back. We've been to Ashland several times before and this is definitely the best place we've ever stayed.

    Well located and cared for accommodations for the 5 of us for the OSF

    5/5 Stayed Sep 3, 2015
    Submitted Sep 28, 2015

    A group of us, two couples and a single, stayed at Sugar's Garden Suite four nights while we attended a long weekend of plays at the Oregon Shakespeare Festival. Each of the couples had our ground floor suites with attached bathrooms, and the single had the run of the two upstairs bedrooms with hall bathroom - this work great as we each had our privacy. The well-equipped kitchen and adjacent dining space worked great for the meals we took at the house. The living room and front porch we're comfortable gathering spots. The beds were excellent, furnishing of good quality, and everything cleaned and thoughtfully provided for. Although only a block from a major thoroughfare, the street and house were very quiet, and we were never aware of tenants in the attached unit behind us. The cottage is also an easy walk to OSF, the Coop for food, and many restaurants, so we rarely needed to use our car while in Ashland. Parking right in front of the house or in the church parking lot to the side was easy and accessible. We had a great stay and would stay there again. Sugar's communications were thorough and accurate and caring. She called shortly after our arrival to make sure everything was okay.

    Perfect location!

    5/5 Stayed Aug 12, 2015
    Submitted Sep 7, 2015

    Excellent stay at Heritage! It is spacious and tastefully decorated. Everything you need to relax and entertain. Wonderful front porch and its in a peaceful location but right in the heart of the best Ashland has to offer! I love the new appliances and FULLY stocked kitchen. Very elegantly put together. Would highly recommend to anyone!

    Wonderful location in downtown Ashland

    5/5 Stayed Jul 10, 2015
    Submitted Jul 20, 2015

    Love this charming rental. I have stayed at this location numerous times but this was my first time with new owner. Noticed a few updates such as Keurig coffee maker!!! Very comfortable cottages / homes on beautiful property. Best location for Oregan Shakespear Festival!!


      Ashland, Oregon

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