
Kid-friendly vacation rentals in Ashland
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Ashland
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Ashland kid-friendly rentals
Kid-friendly house rentals

Charming One
This is the second time I’ve stayed at this location, and enjoyed it just as much as the first time I stayed. It’s clean, comfortable, quiet, well located, and really well decorated. I recommend it highly

Terra Cottage Inn - Quintesential Ashland
I cannot say enough about this listing. We were wishing we could just move in and not go home! Elizabeth and Mark were very gracious, helpful hosts. The listing is cozy and immaculate. The outdoor space is incredible. Ashland is wonderful, as well. We would be willing to move to Oregon, in general, if all our family wasn't here. Thank you Mark and Elizabeth! We hope to return again and visit!

Gorgeous Lakeside HOUSE + Indoor SAUNA!
Words can’t accurately describe how incredible this place is. It’s easily the best Airbnb I’ve ever seen. It’s filled with so many unique and delightful touches, it’s so clean and cozy. We did not want to leave!!

Secluded mountain retreat, 10m. to Ashland, by PCT
This was our second time staying at Mich’s place and we plan to continue coming back! Mich was responsive and easy to communicate with, she goes above and beyond to provide a seamless experience. The home is cozy, eclectic and has everything you need. It’s perfectly located near the PCT for hiking and close to Mt Ashland for easy mountain biking access. The property is gorgeous with lots of opportunities for wildlife viewing. We Would absolutely recommend!

Cute, pet friendly Guest House
A nice, private little place, close enough for a day trip to either Crater Lake National Park or Redwoods National Park

Cute 2 bdr house near downtown (pet friendly)
Great location near downtown, was very easy to walk to food, shopping and OSF shows. The fenced backed yard was great for the pup, dedicated parking was nice. Julia was very proactive with instructions and communication, thank you for being an excellent host!

Cozy Cottage
Laura’s home was one of the best we have stayed at. Clean, modern and pleasantly appealing. Providence hospital and facilities are a few miles away but very easy to get to even on a Monday morning at 8:00 AM. We will book again if or when we need to be in the area again!

Cute Boho w Patio, W/D, Parking (No Chores!)
We had a wonderful weekend stay, the place was just as described. Very clean and nicely decorated. The location was great too! The air conditioner was very much appreciated as well. We look forward to booking again when visiting the area!
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!

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.

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!

Peace on the Rogue river Studio
Kirk and Tandy are amazing host! The house and property are beautiful and well kept. They were very sweet and accommodating. We had a fantastic girls’ trip! Can’t wait to go again!

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.

Light and Bright! Entire 2 Bedroom Apt!
Great place. It was spacious, clean, had everything you needed and comfortable. I will definitely come back again!

Brand New Stylish MCM Studio
This place was very nice and very quiet. It was comfortable and private and made it easy to unload the vehicle and get everything in very quickly. It was our first time in Grants Pass and it happened to be a local event all weekend called the Boatnik. It was a good time and a lot of people for jet boat races and a fair with a lot of people and food. It was fun. We enjoyed our time there. Thank you for being a great host and having the place set up so nice and comfortable.
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!
Quick stats about vacation rentals that are kid-friendly in Ashland
Total rentals
30 properties
Nightly prices starting at
R896 ZAR before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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