
Kid-friendly holiday rentals in Ashland
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Ashland
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Popular amenities for Ashland family-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

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!

Cute, pet friendly Guest House
Had a lovely three night stay for a soccer tournament (2 adults, child, and tiny dog). Small, quaint, comfortable, great location—walking distance to Forage coffee and downtown. Saw roaming wild turkeys in the morning! Wren was immediately responsive and helpful with a bedding question. Had everything we needed. Our dog loved the little grass area. Not a negative but a tip, if you don’t love a firm mattress, I bought a mattress topper and it was magical. Loved the birthday book in the kitchen!

Southern Oregon Gem (EV Charger)
Great spot for a short stay for our group of 3 adults. Very clean and well taken care of. As others have mentioned the neighborhood is “colorful”, but nothing too crazy. The only thing that’s wasn’t ideal is one of the neighbors has a dog they keep outside that barks all night long. Not the hosts fault in any way—-but If you are a light sleeper I would heavily recommend bringing ear plugs. Other than that it’s very convenient and a wonderful value.

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!

Clean and Cozy Farmhouse
I had such a lovely stay. Finding it and getting in was a breeze. The house was peaceful and comfortable and had everything needed for a 5 day stay. The bed was very comfortable as well, slept like a log. Communicating with Cynthia was easy with fast responses to questions. It took me a bit to figure out the internet, Cynthia answered right away and told me what I needed to do. The only thing I regret is not taking a nice hot bath in the deep tub, and I didn't use the epsom salts I bought for a soak. Just didnt get around to it which was a bummer since my tub at home is too shallow to enjoy. If I come back to the area again I will definately check to see if this amazing place is available first.

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!

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!
Family-friendly apartment rentals

Peaceful, Private Getaway in the Forest—new floor!
We had a great stay. The apartment was comfortable and provided everything we needed to feel at home. The forested surroundings were beautiful and peaceful. The hosts were friendly and helpful. They thoughtfully provided a small table, high chair and toys for my children which we greatly appreciated. Highly recommended. Thank you!!

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.

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
Peace on the Rogue was truly the perfect name for our stay. The place is absolutely beautiful, very clean, accommodating, and more. We were spoiled by the serenity of the river, an evening spa and swim after a BBQ, all that was open for us to use. “Come as guest, leave as friends” is an understatement. Kirk and Tandy are such wonderful, kind-hearted, good people. We'll never forget the peace that truly was there on the Rogue and hope to get back soon. P.S. One night really is not enough, but we still left feeling full, refreshed, and very blessed. God is so good.

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.

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.

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!
Family-friendly apartment 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
This is the second time we stayed here. The place is beautiful. Very quiet and peaceful. Plenty of room to relax. This place also has all the amenities.

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 stayed for a week. We found the condo spacious and clean. The neighborhood is quiet and we felt safe. There was plenty of parking for our full sized pickup. The kitchen was well equipped with dishes, pans and utensils. You can walk to downtown, but driving is easier as not all the roads had sidewalks. The building is well maintained and quiet. We plan to stay again.

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.

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!

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.
Quick stats about holiday rentals that are kid-friendly in Ashland
Total rentals
30 properties
Nightly prices starting at
₹4,286 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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