
Kid-friendly holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Ashland kid-friendly rentals
Child-friendly house rentals

777 Hideaway
Super clean, functional space. The host was easy to work with and responsive. Great experience overall.

1912 Home w/Modern Amen-spacious-cozy-dog friendly
Enjoyed staying at this cute 1912 home and all the amenities it provided. Really appreciated the spacious interior and close proximity to town. Thanks Vicki for being very responsive and hope to be back soon. Chris

Rinehart Ranch
We came for my daughters birthday and grandaughters 1st birthday during the week of 8/4. We were able to have family from California visit at different intervals and enjoyed rafting on the Rogue (twice) and a jetboat brunch tour to Hellgate. The property is so beautiful and centrally located for our needs. We enjoyed cooking at the well furnished kitchen and playing in the game room. It was hard to leave and wish we owned a place in this beautiful location!

Chic 4 bed/2 bath house with large yard
The communication was great. That's really important if you're unsure about things. Kitchen was stocked amazingly well with things I needed for baking & cooking. Fenced yard & patio was enjoyed by everyone and there was plenty of room for 4 adult, 2 children & 2 small dogs. We will enjoy our memories made here in Medford Oregon!

1930s Queen Anne Historic Downtown Retreat
This house was absolutely adorable! We loved staying here with the crew. The twin bed upstairs is too small for most grown people especially in the window sill so just make sure to plan accordingly. Everything was clean and wonderful and the master bathroom downstairs with the heated floors and the Bluetooth speakers in the ceiling was amazing. Would definitely stay here again!

🌟30 DAY-25%🌟PET FRIENDLY🌟PRIVATE🌟FENCED YARD🌟W/D🌟
I'm a repeat to King of Queens. Suzanne's place is perfect for my extended stays for work. My dog loves the fenced back yard. Suzanne is an amazing host! I always hope her place is available when I need to go to Medford! Highly recommend!

Private Carriage House
Ed and Jacquie’s place was exactly what we needed. We were on a road trip moving some stuff and towing a trailer, so finding a private, safe spot where we didn’t have to unload everything was a big deal. Their property was perfect, and the pull-through driveway made it super easy to get in and out with the trailer. On top of that, Ed and Jacquie were incredibly kind and welcoming. Honestly, some of the nicest hosts we’ve ever had. The property was peaceful and relaxing, with a creek out back, and the house itself was cozy and comfortable. We felt right at home. I only wish we could have stayed longer! If you’re in the area and need somewhere to stay, definitely stay here. We’d come back in a heartbeat.

New house with king beds and 3 full bathrooms
This place waa perfect for our stay. It had so much room and beds for us. Actually, the open downstairs was awesome and the huge bedrooms provided private spaces for some of our group. It was great.
Kid-Friendly apartment rentals

5 Star Luxury Southern Oregon Suite
Great Host! He was very friendly and responsive and ensured everything was okay. Great price and definitely will return if ever needed!

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.

Suite Comice EV Charging
Jim and his son both were very helpful , and helped me in every way to make my stay the best it could be. Jim was friendly and really listened to my needs during the stay. I loved the place and I was able to park in the driveway for my entire stay. I would definitely stay again should I be back in the area. I could not ask for better people to be staying next to me, in a time of personal crisis.

Classic & Cozy W/D & Parking | close to DT
Cute little place, thank you!

Peace on the Rogue river Studio
We stayed at Kirk’s place for Christmas and it was just perfect! The studio was clean and welcoming when we arrived. Fireplace was on for us and we were able to enjoy the amazing hot tub that night. We had a simple dinner and the kitchen had everything we needed. The two beds were beautiful and so comfy! Not your typical hotel style beds but instead soft and luxurious with thick comfy comforter. Shower had a dispenser for shampoo, conditioner and body wash. The location is also very quiet and the river access was just lovely. Very kind hosts and super accommodating. Would stay here again in a heartbeat.

Great location to I-5 and city! King bed!
The overall stay was comfortable and private. While a few issues arose, it was still a pleasant experience.

Clean, Stylish Apt w/kitchen. block from Downtown
Great spot. Close to downtown and very walkable. Charming interior. Would definitely stay 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.
Child-Friendly Holiday Condos

Black Pearl
This is a really great space! It was much bigger than I thought it would be! It is located literally downtown, but it wasn't noisy. It is very beautiful and I hope to return!

Modern, retro updated bungalow
We traveled to Grants Pass to visit family and Marketa place was the perfect spot. It is very convenient area and quite. The inside was everything we needed and very comfortable. We hope to return!

The Executive Suite
Hands down the best Airbnb experience I’ve had! Such friendly and responsive hosts. The place and location exceeded our expectations, and the place was set up with basically everything you need- even for your pets.

Plaza North Suite 203 Windsor
Everything was perfect and we felt right at home! The place was clean and comfortable and it had everything we needed and more. Easy to walk to downtown Ashland, the CoOp, and the Railroad District. We will definitely stay here again when visiting Ashland!

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
Awesome space. I stayed here and attended UBI which is only a 5 minute walk from the “campus”. Town is an easy walk & a huge bonus was the sauna & spa baths right across the railroad tracks.

Plaza North Suite 201 Alexander
This condo was one of the best AirBnBs I’ve ever stayed in. Everything was new and very clean. The condo is spacious and tastefully decorated with modern, but comfortable furnishings. The closets are huge! The beds were comfortable with nice, newer linens. The tv was easy to use, and although we didn’t cook while we were there the kitchen was well stocked. Checkin was simple, all codes worked like a charm and the elevator took you right to your door. We never saw any other guests. It is within 1 block of downtown shopping, restaurants and theaters. Very walkable. Things quiet down in Ashland at night so there was no noise either. Wonderful host and experience!

Plaza North Suite 202 Sonoma
Upon approaching the entryway, we could not get in, as it was not stated to use the # sign after entering the password, so my daughter and I were stuck for a bit before I tried that. We got in fine after that. Instructions were not clear once inside as to how to operate the heater below the TV. We turned it on, only using the power button, and that was it, as it just was not clear what we could and should not do. The TV was great, however, when using Prime or Netflix, there were multiple accounts, we figured these were from previous guests who maybe forgot to sign off? We just did not know, so we did not touch them. In sum, we had a fantastic time, and your place is amazing, I just put these comments above as I know from previous feedback left, that it is useful, just giving you my full experience is all.
Quick stats about holiday rentals that are kid-friendly in Ashland
Total rentals
30 properties
Nightly prices starting at
$47Â AUD 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
10 properties have a dedicated workspace
Destinations to explore
- Southern Oregon Holiday rentals
- Medford Holiday rentals
- Crescent City Holiday rentals
- Mount Shasta Holiday rentals
- Brookings Holiday rentals
- Crater Lake Holiday rentals
- Grants Pass Holiday rentals
- Klamath Falls Holiday rentals
- Gold Beach Holiday rentals
- Portland Holiday rentals
- Northern California Holiday rentals
- Gold Country Holiday rentals
- Rentals with outdoor seating Ashland
- Condo rentals Ashland
- Cottage rentals Ashland
- Apartment rentals Ashland
- Private suite rentals Ashland
- Family-friendly rentals Ashland
- Rentals with a washing machine and dryer Ashland
- Rentals with a hot tub Ashland
- Pet-friendly rentals Ashland
- Rentals with a fire pit Ashland
- Rentals with breakfast Ashland
- Cabin rentals Ashland
- Rentals with a fireplace Ashland
- Rentals with an EV charger Ashland
- Rentals with a patio Ashland
- Rentals with pools Ashland
- Guesthouse rentals Ashland
- House rentals Ashland
- Kid-friendly rentals Jackson County
- Kid-friendly rentals Oregon
- Kid-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom