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

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!

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

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.

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.

We stayed in the Oak Lawn cottage for the weekend with our dog and had a fabulous time in Ashland…read more The manager was so helpful. The cottage is well appointed, there is nothing we needed (coffee, tea, large bath towels, great bedding). Beautiful garden entry, picket fence, shaded patio with a bbq grill. Space for our pup to enjoy the outside. Within a block of downtown, restaurants, shopping, a dog park and 2 miles from the wineries. We parked our car and walked everywhere. We will definitely be back and can highly recommend for anyone visiting Ashland.

We stayed in the Studio for one night in order to catch "The Tempest" playing at the very walkable…read moreShakespeare Festival. The pictures on the website don't do this little gem justice. The space is so much more than a "studio." There's a sitting area, a small living room, a dining table, a "kitchen area" with coffee, microwave, and full sized refrigerator, plus a bathroom. The bedroom has its own doors that close, which we love because we never sleep at the same time. Anyway, this spot is amazing. And Donna treated us just like upscale Airbnb guests; always available by text. I'd stay here again in a heartbeat.

Location was perfect! We could walk to the theater, restaurants and the shops very easily. We…read morestayed in the Red McCall space which had a separate room for our 11 yr old and a king bed with bathroom access for me and the spouse. It was cozy, had thoughtful amenities and there were notes to help navigate the guest in the space (hot tub use, step stool location etc). The owners have put some time into the remodel and it is welcomed. Also hot tub was hot and ready to use (which was needed for the 40-50 degree nighttime). Highly recommend!

Upscale stay, better than anticipated. Iwill definitely be back. I recommend this place. It's…read moreperfect and right in the heart of Ashland. I promise

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.

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!