Family-friendly vacation rentals in Ashland

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Ashland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Grants Pass

4.94 out of 5 average rating, 450 reviews

Sweet Vintage Cottage steps from Rogue River

Welcome one and all to DunMovin'. The Cottage you will be staying in may make you feel like you have stepped back in time. Don't forget your fishing pole, this property is on the banks of the Wild and Scenic Rogue River. Lounge by the pool, feed the geese, go shopping, or head to any of the amazing restaurants that are just around the corner. I'm in the city limits, so everything is a minute or two away. It's my slice of heaven. I also have a larger unit, search for 'Riverside on the Rogue'

Superhost

Loft in Hornbrook

4.93 out of 5 average rating, 380 reviews

The Green Arrow Loft

Situated right on the state line this studio apartment is nestled in its own little corner of the gorgeous Colestine Valley. We're located on 80 acres that adjoin the Cascade-Siskiyou National Monument to the north, perfect for a scenic hike or a casual stroll. Nature and wildlife abound, and though quiet and private the Loft is just five minutes off I-5 and 25 minutes from unique downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on pet and pool fees.

Top guest favorite

Guesthouse in Medford

4.98 out of 5 average rating, 460 reviews

Comice Valley Inn With E V Charger

Health care professionals please ask about special rate for longer term rental. We disinfect all surfaces before and after new guests arrive. Rest assured. Comfortable, light, clean and airy private two bedroom upstairs guesthouse. Host on location in separate home. Fully equipped kitchen, with breakfast provided, makes this the perfect place for overnight or an extended stay. Neighborhood is quiet and shopping and dining are not far away. Two bedrooms make this a perfect getaway for friends.

Top guest favorite

Home in Ashland

4.92 out of 5 average rating, 232 reviews

Ashland Haus Retreat - 1 block from downtown!

This beautiful 10 foot ceiling home is ideal for your stay in Ashland. Our classic two bedroom 1900s home has many new renovations (floors, appliances, furniture-- all done in August 2017). Enjoy a short walk to great cafes, restaurants and breweries! We are about an 8 minute walk to the Shakespeare Festival. One bedroom has a queen bed, the other has a king bed that can be made into two singles. The sleeper sofa is in living room. The bedrooms share a Jack&Jill bathroom. PA # PA-2017-01160

Superhost

Home in Medford

4.8 out of 5 average rating, 207 reviews

Common Area! Near Rogue X, 3 king beds 82" 4k tv

Huge grassy common area! Big 4k TVs. House is a large 3 bedroom in a nice neighborhood. Must be respectful of neighbors. No dogs left outside barking. There is an HOA at this house and disruptive behaviors are reported and fined. Guest pays all assessed fines! No outside music, no fireworks. This is a beautiful family oriented neighborhood backing up to a Huge common grassy area. There isn't any playground equipment but perfect for Frisbee, soccer, etc. Please treat it respectfully

Top guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 582 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Top guest favorite

Bungalow in Ashland

4.99 out of 5 average rating, 104 reviews

Penthouse Suite, easy walk to downtown.

The Penthouse Suite is the full top floor of the 2 story apartment building, that affords lovely views, and has been completely rebuilt in 2017! New kitchen and appliances, gas fireplace, & in house laundry. It has 3 bedrooms with 1 king, 2 queen, 1 full, & Q futon. It has 2.5 baths. Enjoy huge, partially covered deck, and gas grill. Downtown is 10/15 minute walk away. The local taxes are included in the price, account ID 527. Pets on approval.

Guest favorite

Guest suite in Grants Pass

4.8 out of 5 average rating, 158 reviews

Two room private suite on river, friendly hosts.

Our place has just been remodeled. It is close to public transport, the city center, and family-friendly activities. We are within walking distance of a store, and a great restaurant. You’ll love our place because of the outdoor spaces, the light, and sitting next to the Rogue River watching the rafters, boats, geese, Egrets, Herons, and eagles.. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

Guest favorite

Home in Jacksonville

4.87 out of 5 average rating, 275 reviews

Plymale Cottage Bed & Biscotti - 2BR, Kitchen, AC

4 Guests, 2 Bed Rm, Sitting Rm & Kitchen, the "Hobbit Rm" with toys, teddy bears and a playhouse. Pet Friendly - One (1) small dog (30lbs or under) house trained. My small back yard is not available for a pet. Our upstairs cottage rate is $135/night. Rates do include city taxes, service & c;eaning fees. Guest entrance has stairs and balcony. Kitchenette and small living. TV available in King room. Air Conditioning

Top guest favorite

Apartment in Grants Pass

4.95 out of 5 average rating, 848 reviews

Peace on the Rogue river Studio

Beautiful park like setting on the Rogue river with a jacuzzi, swim spa two decks, fishing, yard games, hammock, barbecues, bicycles, kitchenette has Keurig With pods,a toaster oven, crock pot, small George Forman a portable two burner cook top , small skillet, one pot and most utensils to provide a meal. Minutes from Grants Pass, shopping, restaurants, and winery's.

Guest favorite

Apartment in Ashland

4.88 out of 5 average rating, 789 reviews

Clean, Stylish Apt w/kitchen. block from Downtown

92½ Church Street. A private apartment with a large bedroom, full kitchen, bath with shower. Vintage styling with loads of special touches, ONE BLOCK from downtown. All the comfort of home and so close to the action. Large yard. Permitted. (Ashland City Permit: 15-237). 2020 Update: We have adopted the recommended Covid-19 Cleaning Guidelines.

Guest favorite

Home in Ashland

4.91 out of 5 average rating, 127 reviews

The Madrone House, mountain views.

Located on our secluded 40 acres, this newly built 3 bedroom 2.5 bath, will ensure your family a comfortable stay. Beautiful views of the surrounding hills, and stars at night. The kitchen is readily stocked with spices and appliances, a bbq on the spacious back deck, has ample seating for dinning, facing Grizzly Peak.

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What guests are saying

Unique Log Cabin, beautiful views

4.83 out of 5 average rating, 255 reviews5 months ago

Our second stay at this cabin. Nicely located near a favorite winery, Plaisance Ranch. Beautiful location in Oak Forest. Comfortable rustic cabin with an excellent woodstove kept us warm and toasty during cool, fall weather. We will stay there again, I’m sure. Great hosts!

Cabin in Williams

What guests are saying

Terra Cottage Inn - Quintesential Ashland

4.97 out of 5 average rating, 156 reviews5 months ago

The cottage and the exterior space is a meticulously maintained oasis. The pictures and words describe and show this charming cottage, but it is much more when you see it in person. It's a beautiful Abnb with exceptional owners in a beautiful town with friendly people. I stayed here for a month while attending UBI, a trade school in Ashland. The location was walkable to both the school and downtown (restaurants, Lithia Park, Shakespeare Festival events). The dedicated parking spot for our vehicle was steps from the gated entrance, making groceries and luggage carries a short trip. Ashland itself allows for day trips to the Oregon coast, Grove of the Titans Redwoods (CA), Crater Lake (OR), and Mount Shasta (CA).

Home in Ashland

What guests are saying

Roxy Ann Retreat - Large Luxury Carriage House

4.96 out of 5 average rating, 70 reviews1 week ago

This home was in a quiet, stunning neighborhood with a gorgeous view. We got to watch the sunset from bed! All of the furniture was comfy, cozy, clean, and smelled good. Elyse was so responsive and helped us with a question/request right away. The home was in the perfect center of all of the things we wanted to do while we visited, and so close to a cafe/wine tasting room/food truck spot. We were so happy we chose this place for our long weekend get away.

Guesthouse in Medford

What guests are saying

Bear Hollow Retreat

4.93 out of 5 average rating, 59 reviews8 months ago

My stay at this mountain retreat near Ashland, Oregon was absolutely breathtaking. The panoramic views of the surrounding forests and peaks were stunning, making it the perfect spot to unwind and connect with nature. The cozy accommodations, combined with peaceful seclusion but yet not too far from Ashland’s charming downtown, made this getaway truly unforgettable.

Guest suite in Ashland

What guests are saying

3BD House on the Rogue River

4.72 out of 5 average rating, 139 reviews9 months ago

The river house was the perfect accommodation for our group of 6 adults. We enjoyed exploring the property, spent time on the patio, and enjoyed going up to the lodge for cookies and s'mores in the evening. The host were incredibly kind, helpful, and responsive to messages. We would definitely return for another stay at the river house or cabin in the future.

Home in Grants Pass