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Kid-friendly holiday rentals in Ashland

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Ashland family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Medford
4.97 out of 5 average rating, 116 reviews

Charming One

DirkRating, 5 stars1 week ago
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
Guest favourite
Home in Ashland
4.96 out of 5 average rating, 186 reviews

Gorgeous Lakeside HOUSE + Indoor SAUNA!

JessRating, 5 stars1 week ago
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!
Guest favourite
Home in Medford
4.94 out of 5 average rating, 119 reviews

Cute, pet friendly Guest House

PabloRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Medford
4.88 out of 5 average rating, 339 reviews

Southern Oregon Gem (EV Charger)

MatthewRating, 5 stars1 day ago
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.
Superhost
Home in Ashland
4.86 out of 5 average rating, 99 reviews

Cute 2 bdr house near downtown (pet friendly)

RyanRating, 5 stars1 month ago
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!
Guest favourite
Home in Talent
4.98 out of 5 average rating, 101 reviews

Clean and Cozy Farmhouse

AubraRating, 5 stars1 week ago
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.
Top guest favourite
Home in Medford
4.99 out of 5 average rating, 105 reviews

Cute Boho w Patio, W/D, Parking (No Chores!)

CandiceRating, 5 stars2 days ago
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!
Top guest favourite
Home in Medford
4.98 out of 5 average rating, 193 reviews

Cozy Cottage

ValerieRating, 5 starstoday
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

Guest favourite
Flat in Grants Pass
4.94 out of 5 average rating, 171 reviews

Peaceful, Private Getaway in the Forest—new floor!

JessicaRating, 5 stars2 months ago
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!!
Guest favourite
Flat in Phoenix
4.96 out of 5 average rating, 141 reviews

5 Star Luxury Southern Oregon Suite

AshleyRating, 5 stars1 week ago
Great place with all the amenities and very comfortable. This was my 2nd stay here and I plan to stay again in the future!
Top guest favourite
Flat in Ashland
4.87 out of 5 average rating, 253 reviews

Winner 2024 Best of Ashland! Our Carriage House

MaryroseRating, 5 stars8 months ago
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.
Guest favourite
Flat in Medford
4.92 out of 5 average rating, 177 reviews

Broken Chair Ranch

ElenaRating, 5 stars2 months ago
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!
Top guest favourite
Flat in Grants Pass
4.95 out of 5 average rating, 855 reviews

Peace on the Rogue river Studio

JillRating, 5 stars2 days ago
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.
Top guest favourite
Flat in Medford
4.99 out of 5 average rating, 258 reviews

Madrona Suite

AnitaRating, 5 stars7 months ago
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.
Guest favourite
Flat in Grants Pass
4.93 out of 5 average rating, 147 reviews

Brand New Stylish MCM Studio

PaulRating, 5 stars2 weeks ago
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.
Top guest favourite
Flat in Grants Pass
4.99 out of 5 average rating, 189 reviews

Light and Bright! Entire 2 Bedroom Apt!

PaulaRating, 5 stars4 weeks ago
Great place. It was spacious, clean, had everything you needed and comfortable. I will definitely come back again!

Family-friendly apartment rentals

Superhost
Apartment in Rogue River
4.89 out of 5 average rating, 82 reviews

Black Pearl

VictoriaRating, 5 stars3 weeks ago
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.
Guest favourite
Apartment in Rogue River
4.92 out of 5 average rating, 153 reviews

The Executive Suite

ChristieRating, 5 stars2 weeks ago
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.
Top guest favourite
Apartment in Ashland
4.96 out of 5 average rating, 27 reviews

Plaza North Suite 203 Windsor

KelleyRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Ashland
5 out of 5 average rating, 7 reviews

Plaza North Penthouse

JimRating, 5 stars8 months ago
The condo penthouse was amazing in every way. Beautiful, spacious, clean, and in a great location.
Apartment in Ashland
4.89 out of 5 average rating, 45 reviews

Spacious Modern Condo Walk To Downtown & OSF

DavidRating, 5 stars1 week ago
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.
Top guest favourite
Apartment in Ashland
5 out of 5 average rating, 38 reviews

Plaza North Suite 201 Alexander

DeniseRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Jacksonville
4.95 out of 5 average rating, 19 reviews

Selah House!

MichelleRating, 5 stars6 days ago
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!
Guest favourite
Apartment in Ashland
4.9 out of 5 average rating, 20 reviews

Plaza North Suite 202 Sonoma

CynthiaRating, 5 stars1 month ago
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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