Cottage holiday rentals in Jackson County

Lovely place. The directions from the host are very helpful-our GPS alone got us close but not quite there. One quick warning-the bathroom doors are sliding barn style doors and don’t lock. This is absolutely fine if you’re with other adults-they stay closed if you leave them alone-but a child, or in our case, a small dog with separation anxiety, can leave you with some unexpected exposure that could be a little awkward. I was very glad we were meeting family, not staying with them. That aside, the cottage was lovely. It has a small fenced area that was awesome to let us and the beasties hang out off leash.

This home is in a beautiful location along the Rogue River. it is very lovely with ample space and fun things to do. We loved it here.

Great place to stay and relax! Would definitely visit again!

This property is breathtaking. The sunsets over the vineyard is incredible. Agnieszka in the winery is wonderful. The cottage we stayed in was updated and clean. The host was flexible and everyone on property was welcoming and knowledgeable. We stumbled upon a member dinner and it was magical. The beds were comfortable we had great water pressure! Would highly recommend. Will absolutely visit again.

This was our second time staying here. The surroundings are just beautiful. So peaceful at night. Inside is clean, spacious, and comfortable. The hot tub felt great after being on our feet all day. The gift of wine, cheese, and crackers was a bonus! We thoroughly enjoyed our stay here.

Great rural setting, extremely close to Jacksonville, and close (15-20min) to most anything you’d want to do in the Rouge Valley. Felt very private and peaceful. Beautiful surroundings. Good size Airbnb with three adults and two kids. Good AC. Really can’t talk good enough about the place. I’ve stayed at a few places in Medford and will be looking to book here as my primary Airbnb in Medford.

This is a great location if you want to be right near downtown Ashland! It is easy to walk to Lithia Park, restaurants, groceries, shops, etc. Very quaint, rustic and relaxing, right next to Ashland Creek and fun little art galleries. We would definitely stay here again.

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!

Very clean, adorable, comfy cottage. Location is wonderful for a walk to downtown or Lithia Park. The area feels safe and nice.

My husband and I stayed here for a month to explore Ashland because we plan to move there and wanted to make sure it was a good fit! We loved Ashland, so much live music, nice people, nature to hike! This airbnb was perfect while we explored! We could walk down to the plaza and coffeeshops, restaurants all within walking distance. The space had everything we needed for an extended stay! I would definitely recommend!

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 cottage was perfect for our stay in Ashland. It was comfortable and cozy and we will definitely stay again when we visit Ashland in the future.

I am a retired contractor and the inside of the house was so well done. Looked like a recent paint job which was perfect. I thought it was very well done

Fantastic location, walking distance to Lithia Park, restaurants, theater, shopping, food co-op, etc. The place is squeaky clean and really comfortable. Even though there's just one bathroom, the 2 bedrooms each have a sink and mirror, which was great. Gas fireplace is cozy too. Owners were very friendly and responsive. Highly recommend -- we would stay here again in a heartbeat!

Perfect location just off the Main Street (so quieter than staying in the hotel), and easy walking to the Britt fest. Super cute inside, with thoughtful hosts who gave us an early check in and treats when we arrived. Comfortable bed, private balcony area, wonderful soaking tub. We stayed in the Tigers Den because we knew we’d be eating out and wouldn’t need the kitchen. Perfect for 2 people! We would absolutely stay again.

We loved our stay in the Raven cottage. We had a very peaceful experience and enjoyed being in this neighborhood— the perfect location for seeing the plays and sampling Ashland‘s wonderful restaurants and hospitality. We are grateful to the landlords for their helpful and consistent communication. If we return to Ashland next year, we would love to book the Raven cottage again! By far the most wonderful feature is the deck where you can sit and hear the river behind the cottage. Thank you for a lovely stay!

Very clean, comfortable, and great location to walk everywhere in charming historic Jacksonville. Would highly recommend!

We had a fantastic stay at Oak Street Cottages in Ashland, OR! The location couldn't be better—right in the heart of Ashland and within walking distance of all the main attractions, including restaurants, shops, and theaters. The cottage was beautifully maintained, cozy, and equipped with everything we needed for a comfortable stay. The attention to detail and the warm, welcoming atmosphere truly made it feel like a home away from home. We highly recommend Oak Street Cottages to anyone visiting Ashland and look forward to returning on our next trip!

Our whole theatre board needed a place to work and also allow time for rest and play. This cottage was perfect! Plenty of room for all of us to spread out to work, eat, and sleep. We spent time inside and enjoyed the outside porch and patio. Plus we were so close to OSF and downtown Ashland that we could walk easily to dinner and the Festival. It was incredible! Practically speaking, it was easy to find, parking worked for our carpool, and the amenities were great!

We used this space to hold a couple of days of meeting with clients in the Jacksonville area. This was our second time using Deanna's space for this purpose. It's nothing fancy, but is accurately described and fairly priced. It is perfectly accessible for meeting with older clients, which was the most important thing to us. The location is great for walking somewhere for lunch or coffee in between. We had a little trouble getting in with the old door (which Deanna warned us about prior) but Deanna was extremely responsive with any questions we had about both the house and recommendations in Jacksonville. Deanna is a great host and we recommend using her spot if you're visiting Jacksonville.