Kid-friendly holiday rentals in Jackson County

Had a fantastic stay at Amanda's place. Everything was carefully labeled and it had everything we could think of. The beds were spacious and comfy and the house is close to everything! Would absolutely recommend or stay again.

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!

The place was beautiful, well maintained, so peaceful. We couldn’t wait to get up in the mornings and enjoy by the river or chill in the hammock!

Hannah and Ryan’s place is so thoughtfully decorated and organized. It was exactly as described and as others have mentioned just be aware you enter through the bathroom and there is no kitchen, but they do have a microwaves and dishes for you to use. Appreciated the coffee maker and the AC! The sofa bed worked just fine for our kid. Close to food and a super fun indoor pool at the rec center not far away!

Britt's place is very spacious, extremely clean, has easy parking, and is beautifully landscaped. Britt was very kind in ensuring I had everything I needed and checked in that the stay was going well.

Last week we stayed at Sherry and Tom’s Swiss Arbor house in Medford for a week. This was the sixth time we have stayed at an Airbnb in Medford and the Swiss Arbor house was just perfect for us. We absolutely enjoyed the accommodations, location and communication with our hosts. The space, above the detached garage, was built by Tom. Sherry's design and decor were comfortable, warm and welcoming. A very nice kitchen with modern appliances. The washer and dryer also came in handy. The spacious deck had all the comforts, including a gas grill and umbrellaed table, which was used daily. Also, a great spot to enjoy the wonderful sunsets. The location is central for Medford and surrounding areas. We had great meals in Medford and Ashland restaurant's and visited a few wineries. Enjoyed morning and evening walks in the nearby quiet Neighborhoods. The next visit to Medford the Swiss Arbor House will be at the top of our Airbnb list. Thank you Sherry and Tom.

We loved our stay! The house was beautiful, peaceful, and just a short one-hour drive from Crater Lake. My kids had a great time, and the river behind the house was absolutely breathtaking. We’d definitely come back!

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!

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

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.

The Matriarch 2 was absolutely perfect for a quick weekend getaway in Ashland. Less than five minutes walking distance to local restaurants and the Shakespearean theater. It was safe, clean and convenient. Abby and Matt were excellent communicators, and the whole experience could not have been easier. Highly recommend for those visiting Ashland! We will book again!

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.

We had looked at quite a few other airbnbs in the area and we are so glad we chose The Loft. First a Corgi!!! Who doesn't love a corgi haha. Jhana was so cute, very friendly and loved to play and hangout. It was easy to find, easy to access, and a good size for just the 2 of us. Its a very central location everything we needed was no more than a 10 minute drive. The neighborhood is safe and quiet. Pat was absolutely wonderful. From the snacks upon check in to the conversations and recommendations, she was the best! Even my dad said airbnbs typically are not like this. It was out first time using airbnb and we were more than pleased with everything. Thank you!

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!!

Valisatie’s place is the among the nicest places we have had the pleasure of staying in. We were there for five nights. The condo is so spacious, sparkling clean, so well located for OSF, hiking and more. It is bright and the kitchen is extremely well appointed. It is like staying in a high end hotel with a jumbo suite-there was a bottle of wine and snacks waiting for us at check in!! Communication with our host was timely and seamless. Highly, highly recommend this property!!!

Suite 202 was welcoming, clean and well stocked. Every detail was considered: stocked kitchen, laundry/dryer with detergent + dryer sheets, nice bath products, plenty of towels, blackout shades, fast WiFi, powerful AC/Heating, etc. Location has easy parking, and is walkable to everything we needed. Couldn’t have asked for a better stay for ~3 weeks. Valisatie was very responsive to all our questions and requests — thank you so much!

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!