Cottage holiday rentals in Ashland

This an incredibly beautiful and peaceful setting! Amazing place to unwind with plenty of adventures nearby!

very conveniently located and super cute inside. bed was very comfortable. I loved being able to hear the river and the hot tub was the perfect touch. the bed was also incredibly comfortable. would definitely stay here again.

We absolutely enjoyed our stay and exactly what i needed for a weekend away . We will definitely be booking again in future.

Stayed with Stay Rouge for a week. Communication was great and the response return time was very fast! Would stay again!

Beautiful location and views of the valley. Didn’t realize it was connected with the winery which was a real plus! Food and wine and service at the winery was spectacular.

We enjoyed staying here very much! The home is in the country very close to Jacksonville, a very cool old West town. Medford and Cenral Point were just a few minutes away. It was so peaceful and quiet here! Having a full kitchen helped, as we cooked breakfast both mornings of our stay. We will try to book this place again when we are in the area again. Don't hesitate at all, this is a great place with great hosts!

Margaret and John were great hosts and their place was absolutely lovely. The interior of the Carriage House is beautifully decorated, comfortable and has all the amenities one could ask for and more. The surrounding garden was peaceful and beautiful with many blooming flowers. The location was perfect, in close proximity to Lithia Park and down town. Margaret provided us with the very best home made granola, fruit, coffee and oat milk which was an extra treat and the kitchen was well stocked with cooking supplies. We highly recommend staying here!

From watching the sun rise with my coffee in the morning to watching the sun set with a glass of wine in the evening, Mary's cottage was a peaceful country getaway! I thoroughly enjoyed my stay!

The family and I had a wonderful experience staying at The Red Dragon House! The house is clean, the hosts are friendly and responsive, and the location is peaceful. This is a great place to stay if you don't mind being just a few minutes from downtown Ashland - for us, this was preferable. There are thoughtful touches throughout the house, and you can tell the hosts spent time considering the care and comfort of their guests. We've stayed here twice now, and can't wait to return for our next visit to Ashland!

what a beautiful location. river view was beautiful, river access is a little tough, but managed. Steve and Jayne are super friendly and although they live above, we really never heard them. It was a great stop for our mini Vaca and would love to revisit.

A tranquil setting, magnificent surroundings, beautiful house, and Elizabeth and Richard are particularly gracious hosts: what more can I say? My daughter and son appreciated easy access to Mt Ashland Ski Area only 15 miles away. Can’t wait to come back again. Pierre

The studio is a cozy snuggery! Some highlights: super comfortable bed, fun art in bathroom, cute flannel sheets with woodland creature print. But the best part was GG herself. Even before I got to town, she was able to give me insider information….the restaurant I wanted to visit would be closed on that day. Then, the night I arrived I took several wrong turns on my way to the property and needed a LOT of help from her to find my way. GG even stood outside the house on that bitterly cold night to guide me in. So kind and helpful! A wonderful experience!

Sugar’s cottage was a great place to stay for the holidays with my family. Very cozy and great location.

We had a peaceful time. Our niece got married on the property. We could easily walk to the big farm house and then walk back to the cottage. The beautiful bamboo blocks all the noise from the road and the guests at the other house. It is a lovely setting and very comfortable.

I very much enjoyed my recent long weekend at Lisa and Craig's Ashland cottage. I've visited Ashland many times, but was not acquainted with this area of town. I really enjoyed walking in the residential neighborhood, as well as strolling to the plaza and to plays at OSF. A really lovely area, with a quiet and peaceful vibe. Lisa was very friendly and proactive with communication. Check-in was clear and simple and everything was as described. The cottage was roomier than I had expected and perfect for my weekend stay. Check-out was equally effortless and it was nice to meet the hosts as I departed. Would definitely stay at this Ashland cottage again. Thanks, Lisa and Craig!

This was our second visit to this property. Our first one was just for a night, I think; this time we had 4 nights, and it holds up for a longer stay. It's a quiet and peaceful spot at any time; this time the hosts were away, so we had the entire property to ourselves. The location is simultaneously rural and isolated, and conveniently central to Ashland, Talent, Phoenix, Medford, and Jacksonville. The cottage is comfortable and well appointed. The kitchen is compact, but not frustratingly so - we were able to do the amount of cooking we wanted without issue. The whole space worked well. We enjoyed are stay and would be happy to return again.

Great little cottage within walking distance to all that the charming town of Jacksonville has to offer! Best part is being able to hear the music from the Britt Festival right from the patio. Loved that Margaret provides everything you need for a comfortable stay.

My wife and I would stay here again for sure...super perfect location for doing all things Jacksonville

We visit Ashland twice a year and prefer lodging that allows us to safely park our car for days, while walking everywhere. This fit the bill perfectly. We enjoyed making breakfast & lunches in the cozy kitchen, and enjoyed dinner at numerous top-notch restaurants. As others mention, bed was quite firm but very comfortable for us. Cute, historic cottage with new updates throughout giving you old world charm with modern amenities. Layout and size seem perfect for two. Really appreciated the coffee and cold drinking water options. Would definitely stay here again. We hoped to enjoy the patio area, but rain and cold kept us indoors. Parking area was roomy, safe and easy for our SUV. Thanks for a lovely vaca, Julie!

Sheri’s place never disappoints. Spotless, beautiful decor, kitchen is fully stocked, and Sheri checked in to make sure all was good. We have stayed here several times and will again in the future!!