Kid-friendly holiday rentals in Jackson County

This place was amazing. Our whole family loved and enjoyed each minute. The back yard was peaceful. Our family played in the backyard, ate together, and enjoyed the privacy. We had to extend our stay a few more days. The request to extend was responded to quite fast and approved. We come to this area quite often and will be staying here moving forward.

We had a wonderful stay! Thank you for being helpful, accommodating and flexible with our requests. We were very comfortable. It was very clean. Very nice neighborhood and community. We highly recommend! Thank you again Michelle for your hospitality!

This was our 2nd time staying here, and it was great! Steffanie was a great host and the house felt like a home away from home. It matched the description and had everything we needed and more.

Beautiful cabin in great location! Everything was clean and fully equipped for cooking and relaxing with family and friends. We had a great stay!

We loved our stay here. Great location... walkable to restaurants, coffee shops and grocery store in Talent, and easy drive to Ashland, Phoenix, Medford and Jacksonville. House is cute, cozy, private, clean, and has everything you need for making meals at home. Beds and bedding were very comfortable. Highly recommend!

Fabulous location right off of the I5 about 10 miles north of Medford. Sparkling clean, with those extra touches that make it really feel like a home. There is a 50 amp EV charger available at no extra charge. Plug is a J1772 so Tesla folks bring your adapter. Yoga mats, comfortable beds, and ample air conditioning were just a few of those extra touches. We even had the privilege of meeting one of the co-owners while staying which was a treat. Great space when visiting the Shakespeare Festival in Ashland, seeing a show at the Britt, or just passing through like we were. We will be back!

I have stayed at a lot of places but this was by fare the most pleasant place to stay. I make a yearly trip to this area to fish and will stay no place else from now on. Clean and comfortable, with privacy to relax.

Hannah’s place was super cozy, clean, and sweet. I’d highly recommend it to anyone wanting to be close to downtown. The space was well-stocked and relaxing with plenty of space. I loved the separate living room and bedroom, and the great use of space even in the small footprint. The historic house also still had the beautiful original windows and hardwood floors that made it feel very homey. You can tell she takes great pride in her house, and it was a pleasure to be there. Hannah was super helpful and responsive at all times! I’d definitely go back for another stay.

We had such a great stay! The home was clean, cozy, and incredibly comfortable. Linens smelled fresh, towels were soft and plentiful, and the space had just the right amount of amenities in both the kitchen and bathroom. We especially appreciated the generous supply of coffee pods and the spotless Keurig machine. The cleanliness really stood out—every corner of the house was spotless, odor-free, dust-free, and sticky-free. It didn’t feel worn or grimy like some rentals can. The large TVs on both floors were a bonus, fully loaded with entertainment apps for winding down at night. The pull-out bed on the first floor was surprisingly roomy—my 6-foot-tall teenager slept like a dream. All in all, a well-kept, welcoming space. Highly recommend!

This was a great place! We were able to check in early and they responded super promptly and were very kind. Place was super clean and was just right for us! I really appreciate you guys and allowing us to spend some time in your place!!

My husband and I were in Ashland for the Shakespeare Festival, and enjoyed a fantastic stay at Katy and Jesse’s cottage-above-the-garage. They were delightful hosts who were quick to answer questions, but gave us plenty of space to make ourselves at home. The location was perfect— super quiet and a quick walk to theaters and restaurants. Everything was clean; the air conditioners were nearly silent, and the uncluttered, well-equipped space worked beautifully for us. Highly recommended! We look forward to returning!

It was just what we needed and the bed is the most comfortable I’ve been on

All good, just tough to find the first night after dark. Lovely little bungalow feel.

Well worth the 14 minute drive out of town. The ranch is gorgeous with thoughtful features throughout (fire pit, roping practice, rope swing, seating areas with the best views in mind). We spent the majority of our trip just enjoying the house and space as the entire ranch feels like a vacation! Quiet. Hut tub was clean and warm. The pool was lovely, we would consider coming back in the summer just to enjoy the pool!

We have been staying here for years, and this is THE perfect spot for a getaway weekend to watch plays. A short walk to the shows, breakfast down the hill, high tea a block away. The room is spotless and the full kitchen is a blessing.

Jennifer has gone above and beyond to make Suite Madrona a very comfortable place to stay. I was there for a full week and could not have asked for more. She has attended to every detail. In addition, she recommended some wineries in the area I did not know about. This lovely enclave is only 15 minutes from Ashland without charging Ashland prices, and very close to the airport. I highly recommend Suite Madrona.

What a wonderful place! It was spotless and had everything needed for a great stay. Ryan was extremely helpful and responsive. There is a lovely coffee shop just outside and plenty of nice restaurants in the area. I would definitely stay here again and have already recommended it to my family.

Beautiful home with several things conveniently located nearby.

We visit Ashland regularly to visit family. I’ve traveled a lot, and this was one of those rare good finds. The host is wonderful, and so is the place. I loved the modern, minimalist, yet natural and warm interior and it’s very convenient (the Co-Op, etc). It was very quiet, too. We’d stay here again in a heartbeat.

Well appointnted, modern, clean place, centrally located in downtown Ashland. Would happily stay again.

We come into town every few years to visit a relative in Medford. This is the first time we stayed in Ashland. We just love both Ashland and this condo as our springboard to the town of Ashland itself, and the Ashland area. The hiking nearby is amazing- so many options within 20-30 min. drives. The unit is spacious and very well appointed in terms of furnishings and kitchen equipment. We loved the view of the mountains and the shifting lighting from the private balcony, and the living room windows. We made use of open windows for airflow. The unit is close enough to town to walk if need be, but also enough removed from town to be serene, with breezes flowing through the unit. When the temp hit 100 ° we made use of the excellent air conditioning systems. Ashland is such a fun town- shopping and restaurants galore, plus hiking right from downtown Lithia Park. Communication with Claudia was smooth, and her instructions were all clear and easy to follow. Highly recommend!!

Second time here...just fantastic place if you want to be in Ashland and be able to walk around the main downtown area. Can't say the two plays were particularly memorable, but the town is still fun and this airbnb is a wonderful space all round. Wish there were units like this in many other places!

This is my second stay at the condo. I love the location as everything is walkable from this spot. Didn't need my car at all during my 4 day stay. The space gets great light and there are nice views of the surrounding hills. Everything worked great and the entire condo was spotless. If one were planning on doing a lot of cooking, you would need to bring provisions as only salt/pepper and oil are provided. Not a concern for me as there are so many restaurants nearby, and the Ashland Co-op is just down the street. Nice to be so close to everything and yet also in a nice, quiet location. I will be back.

We were too late to book a place in Ashland and so we picked this one instead. It was a great choice -- only 30 minutes from Ashland and in the super cute (and historic) neighborhood of Jacksonville. The condo was very cute, spacious, and provided for all our needs. It was a special treat to be able to park in the garage. We'd come back!