
Kid-friendly vacation rentals in Jackson County
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Top-rated kid-friendly rentals in Jackson County
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Popular amenities for Jackson County kid-friendly rentals
Kid-friendly house rentals

Clean, comfy, pet friendly & fully stocked
This was just a short stop for me, but I could feel the care and heart that’s been poured into this place the moment I walked in. It’s beautifully decorated, cozy, and truly one of the most thoughtfully prepared stays I’ve experienced. You can tell the owners genuinely love this home and want their guests to feel welcomed and cared for. From the basket of goodies to the fully stocked bathroom (yes—Qtips, feminine products, all the little things you always wish places had), it’s clear they go above and beyond. Those extra touches? They don’t go unnoticed. The home was spotless, peaceful, and warm—and I left feeling grateful. Thank you for your kindness and for creating such a lovely space. It’s rare, and it’s deeply appreciated.

Chic 4 bed/2 bath house with large yard
This Airbnb was lovely and decorated so nicely; felt like home. I loved the kitchen, it was well stocked with the basics, like sugar, spices, a variety of utensils, pots, pans, tin foil, olive oil; when traveling, you don't want to haul these items around, it was a plus to have these items available; you don't find too many Airbnb's with these amenities. The location was perfect, we were in Medford for our son's wedding, being held at Edenvale Winery, 6-8 minutes away, as well as Jacksonville, where we held the rehearsal dinner. Our daughter, son in law, 3 grandchildren, 2 pups, my husband and myself fit very comfortably in this home and the fenced backyard was also lovely for all. The attention to details and the hosts friendly welcoming attitudes, made our stay a lovely memorable experience. We will certainty be using this Airbnb again in the near future.

Hot Tub huge yard 5 kings fiber wi-fi 4k huge tv
A great experience from start to finish. The house was clean and well appointed. The 5 king beds were all clean and comfortable. Great televisions and a nice backyard. Small details were the key to a great home. A wonderful set of knives in the kitchen and all the spices you could want. You’ll love this house!

Gorgeous Lakeside HOUSE + Indoor SAUNA!
So beautiful! We absolutely loved this Airbnb. We came up here for my partner’s birthday. We were looking for a clean cute home with stunning views/surroundings, and definitely got that here! Would definitely return. A very well done space & enjoyable amenities. Our hosts were also very accommodating & kind!

Fieldside~king bed~pingpong
True Serenity! My family and I enjoyed our stay at Hao’s place. From the morning coffee looking into a beautiful field of gold to the evenings with a cocktail enjoying the sunset. The unit was clean neat and orderly. All The amenities you could want in the kitchen and a delightful playroom in the garage. The unit is so close to all the shops and was in the perfect location for our travels. We were able to visit Mt. Shasta, Lassen Volcano, Crater Lake and The Redwoods! What a wonderful time in Medford and a great host. If we are ever back in the area we will be staying at Hao’s place!

Hygge Hideaway. A home for rest and adventure
Great place, private and beautiful deck and vibe of the interior is beautiful. Feels more spacious than it looks. Great hosts, very communicative and helped give hike suggestions. Very cool to see turkey and deer roaming around too!

Historic Upstairs Apartment
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.

Log Cabin w/Treehouse & Zip Line on Rogue River
The property was beautiful and the home was quaintly decorated and had a cozy cabin feel. The beds were very comfortable and the kitchen was spacious. The whole family enjoyed the zip line and priceless memories were made! I would absolutely stay there again. We didn't want to leave. Access to the cabin was about 2 miles down a dirt road that allowed us to frequently see deer relaxing nearby. Spectacular!!
Kid-friendly apartment rentals

5 Star Luxury Southern Oregon Suite
Great place with all the amenities and very comfortable. This was my 2nd stay here and I plan to stay again in the future!

Peach Street Super Suite
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!!

Winner 2024 Best of Ashland! Our Carriage House
This is easily the best experience I’ve had using this app. This host is responsive, and the accommodations are exactly what you’re hoping for. Specifically if you’re visiting for OSF, this location is the bomb because it’s not down downtown so it feels quaint not crowded and the restaurants nearest don’t fill up as fast as they do closer to theaters. Having a Safeway across the street is a dream.

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

Classic & Cozy W/D & Parking | close to DT
All good, just tough to find the first night after dark. Lovely little bungalow feel.

Broken Chair Ranch
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!

Clean, Stylish Apt w/kitchen. block from Downtown
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.

Madrona Suite
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.
Kid-friendly condo rentals

Black Pearl
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.

The Executive Suite
Such a great spot. Beautiful space. We enjoyed our time and felt well rested after a long travel day.

Plaza North Suite 203 Windsor
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.

Plaza North Penthouse
The condo penthouse was amazing in every way. Beautiful, spacious, clean, and in a great location.

Spacious Modern Condo Walk To Downtown & OSF
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!!

Plaza North Suite 201 Alexander
Really enjoyed our stay. The condo is very spacious, comfortable, with great natural light. Perfect location for the theater and restaurants. We loved it and plan to return.

Plaza North Suite 202 Sonoma
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.

Selah House!
Incredible spot! Location is perfect for visiting downtown Jacksonville and the local wineries. The apartment itself was perfect for our family! The vintage-style arcade machine was delightful for the kids and everything was well thought out. Amazing master bed/bath! Highly recommend this place!
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