My family (including 4 kids) and my parents rented the Cottage and the Garden studio for several…read moredays. We had a blast. The owner is friendly and always accommodating. The sitting on horses, feeding chickens and trampoline were big hits with the little kids. The location of the ranch is just south of town, but still very accessible to Ashland and Medford (and the winery next door!). The owner was great about cleaning the grill for us and responded quickly when we had an issue or a question. All and all, a great trip, and beautiful ranch.

Beautiful country ranch with warm and gracious hosts. The ground floor apartment slept the three of…read moreus very comfortably. It even got chilly at night and the little electric fireplace warmed us right up. Just minutes from town and sooo beautiful, peaceful and quiet. The stove, microwave, and fridge were a great bonus. Would highly recommend it. Debbie and Jeff are amazing!

Recently stayed here and loved everything about the Lark cottage! Frequent Ashland every year for…read morethe last 14 minus Covid and this has been added as one of my favorites. Owners are very responsive and pet friendly. Parking is easy onsite and there's also plenty of street parking in the quiet neighborhood. The cottage is very accessible to town, across the street from the co-op. You can pretty much ditch your car for the entire time of stay and walk pretty much everywhere. Farmers market, beasys and local coffee shops are a plus. Cottage is very clean, well stocked and just as advertised. Thanks again to the owners! Loved everything about your beautiful cottage.

My son was going to attend the bicycle University right down the road so we set up a month for him…read moreto be down there and staying at the cottages, though that did not work out for him to come down and attend. I still wanted to give a shout out to Jamie who is so awesome to deal with setting up the reservations and then having to cancel. Communication was great. Thank you and I would definitely recommend them

The Delaunay House is the jewel of Ashland! You couldn't find a more centrally located guest house!…read moreWe enjoyed our stay so much because of the location, the decor and the sense that we were in a special house.. Deborah Delaunay has done a fantastic job of creating an elegant, functional, and wonderful place to be when wanting to really experience Ashland. All within 2 blocks: the Ashland Food Coop, the Oregon Shakespeare Festival, the Ashland Armory, the creek and the downtown plaza. Its just crazy good!

This place is for sale, so they probably don't care anymore. This place is an absolute dump, with…read moreold dusty, creeky furniture and none of the charm shown on the website. It is between two outdoor cafe/bars and the Armory so getting sleep with all the noise is impossible. The place reeks of gas. Deborah, the owner is rude, arrogant and unresponsive. She claims that she is nearby, but when we called because of the smoke alarm, she didn't call back for three hours and then just told us to take the batteries out ourselves. We complained about the gas smell and she said don't worry about it. Why is this woman in business! Even though we had rented the whole house for the weekend, she called us at 11am and demanded that we drop everything and move our things out immediately because she wanted to show the house to someone that afternoon and wanted to have her cleaners come in. When we tried to talk with her, she complained and whined while her guests, including a 94 year old gentlemen, moved things to accommodate her. Awful woman and an awful drafty old house.

Quiet. Secure. Incredibly comfy bed, pillows, and bedding. Bathroom completely remodeled and…read moreamazing.

This place is so beautiful and very cozy! Thankfully they also have rooms for dog owners, as we had…read moreour sweet dog with us as well. The rooms are well equipped and very comfortable! The front desk manager was very helpful & welcoming. I would definitely stay here again :)

Sylvie and her team are professional, friendly, and very responsive to client needs. Highly…read morerecommended!

We had a great experience renting with these guys. Great communication and easy to use portal to…read moremake requests and they were always quick to respond. They also helped us find another place to move to when our lease was up. Highly recommend!

It's beautiful. The host is wonderful and the views are incredible. If you just want to relaxing…read moreplace to decompress and enjoy the beauty that is part of southern Oregon. This is the place to stop.

From the owner: We have the best views in Ashland. We have the most private oasis to stay at. We have a calm and…read moreprivate place for family vacations. We have a perfect spot for a wellness retreat. We have an awesome home to stay at

Stay here! You won't regret it…read more The setting and the hosts are wonderful. The rooms are great and comfortable. The grounds are nice and peaceful and even have a koi pond. Everything is within walking distance.

We resist the urge to so highly rate a place such as this, because it usually means we won't be…read moreable to get in again, it becomes so popular! But here goes... The innkeepers are ttruly charming folk who provide a beautiful experience with simple yet perfect accommodations. The setting couldn't be better and the location is ideal, situated almost downtown, half a block to the shops, bookstores, bars, and restaurants of the village. We rented a lovely one bedroom apartment for the most reasonable price. Best of all, walking distance to Caldera Brewery tap house! We loved doing laundry at Henry's laundromat, where we would visit the Book Wagon used bookstore next door. One has to drive to the laundromat, and the adjoining bookstore, but it's not a long drive. The location is also ideal because it's on the Northwest part of town closest to the town of Talent, where we enjoyed shopping for books, antiques, and other items.

Lisa is absolutely the best. She goes above and beyond for her landlords. Does an amazing job. Has…read moregreat insight. Cannot recommend enough.

LONG STORY BELOW. BEWARE!…read more THE OWNER OF ASURENT, LISA PETRINI, THREATENED ME FOR MY HONEST REVIEW! I slightly revised this review, today April 29, 2026 as a few problems were resolved on April 28th. Lisa, I investigated the law and you have nothing on me. This is protected speech. Have your lawyer check the S.L.A.P.P. law. I'm retired and I'll be happy to go to Medford several times to see you in court. There will be no arbitration on your efforts to stop me from exercising my First Amendment rights. Our experience has involved serious issues with financial handling, communication, and decision-making. The owner, Lisa, withheld over $500 from our owner disbursement, claiming an unpaid utility bill with the City of Ashland. This claim is incorrect. I contacted the City directly and received written confirmation that somebody (I thought it was the tenants, but, Lisa said it wasn't) established their own service, our account is fully paid, and the landlord account was closed. I emailed the city's communication to Lisa. Despite this, Lisa refused to acknowledge the City's confirmation and continued to claim she did not received a response from them. SERIOUSLY BAD NEWS REGARDING UTILITIES. TENANTS BEWARE!!! Added tonight on April 29, 2026 - The City of Ashland emailed me. Lisa Petrini, owner of Asurent, closed the utilities account for the property and left the tenants without utilities, including electricity, water, sewer, and other city services. The missing smoke and carbon monoxide detectors were photo documented during the original walk through with the staff of Asurent Property Management. See below for the response I received from Lisa Petrini. The original review was dated April 24, 2026. On April 28, 2026 Lisa threatened me for the review. I revised the review on April 29, 2026. We were also informed that tenants reported a gas smell--an issue that should be treated as an emergency. I immediately directed our contractor and Jahnke (HVAC) to inspect for a potential gas leak, as Asurent indicated it may be related to the HVAC system. Asurent then stated that the gas company had already responded and shut off the service. However, when our contractor and Jahnke arrived, the gas was on, and no leak could be detected using their equipment. During this same discussion and following threats, Lisa claimed that required smoke and carbon monoxide detectors were not present. This is highly questionable. The home was fully remodeled prior to engaging Asurent, and all required detectors were installed. Asurent also completed an initial walkthrough with us at that time. Given the inconsistencies already noted, this claim raises further concerns. Lisa claims she has the walk through documents stating that there are missing detectors. I ASKED HER FOR THE WALK THROUGH DOCUMENTS IN ORDER TO ENSURE THE DETECTORS WERE NOT PRESENT. SHE HAS NOT PROVIDED ME WITH THESE DOCUMENTS. We've experienced holds on our net proceeds (deposits minus expenses) that were not released until my threats were issued. See above about the threats from the property manager. We have encountered inconsistent information in regards to utilities, expenses and repairs. Based on this experience, I cannot recommend this company to other property owners.

Spent two nights at the Jessel House and would agree a 3* review is most appropriate. The…read morepositives would be the location is within walking distance {1+ mile} of downtown and the property itself {patio and outdoor firepit area} are beautiful. The Homeowner was very responsive during VRBO communication and sent a very lovely RSVP via mail to confirm our stay. The not so positives - walking in the house it appears to be both neat and clean, but once settled in that's not the case. There are cobwebs everywhere and all of the furnishings and the house in general needs to be more thoroughly cleaned and dusted throughout. There was mold in the shower and on the tiles and also on the inner shower curtains in both bathrooms - this needs to be addressed@ Our reservation was for six and there were only two rolls of tp in each of the bathrooms which we quickly ran out of. The furnishings are a bit outdated and the two twin beds in particular really {really} need new more comfortable mattresses - they're very hard and not very comfortable. We had no hot water at all the first morning of our stay. We contacted the house manager first thing in the morning, who did eventually reply after about an hour of calling and texting. The Homeowner, who we also called when we couldn't reach the house manager, did not respond to our call. House manager did finally respond and open access to the downstairs flat so that we could shower which we greatly appreciated. Apparently, a breaker had tripped but once reset we did have hot water for the remainder of our stay. Overall, I really think a thorough and deep cleaning, updated mattresses and ensuring the home is equipped for the number of guests staying here this would have easily been a four-star review.

Friends and I wanted to spend a week in Ashland, but started planning way too late (2 months in…read moreadvance)....everything was taken except for the Jessel House. So we plunked down $1700 for the week to rent the upper unit (3 bedrooms, 2 baths), and were sorely disappointed. It's an old house that is in great need of updating. The landlord and handyman had to come over 3 times during our stay! They had to fix a long list of items: running and leaking toilets and swamp cooler, dull rusty knives, doors that stuck or didn't close, inadequate and dirty linens and blankets, a nest of bees outside (with frequent visitors inside), funky furnishings and beds that had seen better days, a spotty wi-fi. The owner was prompt to come over, but would argue about repairs or our suggestions to improve. He did finally fix most of the problems, but we ended our stay with a vow never to return. For the money, it was far below the quality of most vacation rentals. We did think the location was nice (7-8 blocks from the OSF), quiet, and with a decent yard.

Sugar has such a lovely place! So inviting, clean, and comfortable. The front porch is wonderful…read morefor morning coffee, an evening meal, or wine with friends. The main home is roomy and was wonderful for our whole family! The kitchen is well equipped and we were able to make most of our meals together. The cottage is within walking distance of many delicious restaurant, however. And downtown Ashland is full of interesting shops, coffee, places, as well as the Oregon Shakespearean festival, a world class theater. Second Street Cottages was a terrific find and we will be back! Sugar is the BEST!!

Absolutely beautiful location The cottages, are immaculately kept and so lovely! I've stayed at…read morethis location many times and have never been disappointed! The owner is so sweet and accommodating as well.