Family-friendly holiday rentals in Jackson County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Jackson County

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

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Guest favourite

Guesthouse in Medford

4.92 out of 5 average rating, 392 reviews

The Greenwood Villa w/wood fire hot tub

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

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Home in Talent

4.79 out of 5 average rating, 109 reviews

Downtown Talent 2 BR bungalow

Sunny, Quiet, and clean in downtown Talent! Market, coffee shop, cafes, food trucks, Camelot Theater, library, playground, winery & shops in easy walking distance. Centrally located right between Ashland & Medford for discovering up and coming Talent while exploring the Rogue Valleys offerings: wine tasting, Oregon Shakespeare Festival, Britt Festival, historic Jacksonville, skiing or outdoor adventuring in mountains, or on rivers or lakes. We're dog friendly, but no dogs on furniture please.

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Home in Trail

4.95 out of 5 average rating, 227 reviews

Log Cabin w/Treehouse & Zip Line on Rogue River

Serene, large log home in the woods w/matching tree house fort. Located in Trail, Oregon on 120 acres of forest views and has a 1/2 mile of river frontage on the wild and scenic Rogue River. The property is near to several lakes, waterfalls and scenic hiking trails and is located directly on the way to Crater Lake National Park. Home is located at the end of the road and provides lots of privacy, peace and quiet. The nearby river can be heard from the cabin providing a peaceful environment.

Top Guest favourite

Guesthouse in Medford

4.87 out of 5 average rating, 136 reviews

Lotus 2-Peaceful-Well Stocked-W/D-Walk to Park

-No Checkout Chores- The Studio is a comfortable and relaxing place to wind down after exploring the area. It is above the garage of my home with a side entry. The full kitchen is well equipped. It has a Keurig, coffees, teas, creamers, sugar, cooking oil and spices. Vaulted ceiling and ceiling fan. The bathroom is a good size with a jacuzzi tub/shower. The walk-in closet has an energy efficient washer/dryer-laundry supplies included. Located 2 blocks from a major park-Fitchner Mainwaring

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Home in Medford

4.82 out of 5 average rating, 303 reviews

Hillcrest 4br 6 bed, last minute ok, 75" Qled TV!!

Hillcrest CLOSE, granite counters in kitchen and bathrooms, yard, Views, 2 balconies with tables and chairs to relax outside. double headed shower in master. New house, built in 2015. Dual temp controls. Written approval for all pets!!!! Not fenced. Keurig or regular coffee pot. Comfortable couches. Stunning 75" Samsung 4k QLED tv in living room! Add in sonos soundbar for the full experience. New 4k 55 samsung in master Upstairs is a huge bedroom/play area big screen tv and 3 queens.

Guest favourite

Cabin in Medford

4.86 out of 5 average rating, 107 reviews

Woodland Cottage near Jacksonville Dog Friendly

It seems remote, so your nervous system relaxes on 60 acres in nature's stillness, yet it's only 10-minutes drive to Jacksonville or Medford; 25-min to Ashland. Long stays welcome. Our sanctuary has modern comfort & convenience, a king + queen bed, 2 sofabeds, full kitchen, TV, large library + views. Our land supports evergreens, gardens, ranch critters (chicken, dogs), a shallow pond, hilly hikes to BLM trails, peaceful places to hang out. We welcome Canine Companions ($30/week fee) & Kids.

Top Guest favourite

Guesthouse in Ashland

4.99 out of 5 average rating, 595 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.

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Guest suite in Jacksonville

4.83 out of 5 average rating, 287 reviews

Claudia's Retreat Sanctuary

Retreat here on my 6 acres of madrone forest with pastoral views, 2 meditation labyrinths- yet only 3 miles to the quaint, historic town of Jacksonville, Oregon, home of Britt Festival, 35 minutes to Ashland and 1.5 hours to Mt. Shasta or Crater Lake. This guest suite in the lower level of my house. Walk the spiral labyrinths. Book a Sacred Sound bath session with Tibetan and crystal bowls & Paiste gongs for $70 during your stay. Massage chair available too. Simply divine!

Top Guest favourite

Guesthouse in Central Point

4.94 out of 5 average rating, 796 reviews

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1-2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and miles of wilderness. Come enjoy! We celebrate diversity!

Top Guest favourite

Farm stay in Talent

4.94 out of 5 average rating, 310 reviews

Artistic Airstream with panoramic views

This beautifully rebuilt Airstream, makes for the perfect cozy getaway. Perched on its own terrace on a 5+ acre Italian style estate you'll be surrounded by spectacular views, an abundance of fine food, entertainment (including the world famous Shakespeare and Britt Festivals), nightlife, endless family-friendly and outdoor activities, day trips to destination wineries, redwoods and Crater Lake. 4 mi. from downtown Ashland and 13 mi. from Medford airport.

Guest favourite

Guesthouse in Ashland

4.9 out of 5 average rating, 398 reviews

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

Top Guest favourite

Bungalow in Ashland

4.96 out of 5 average rating, 331 reviews

Historic Stage Coach Stop

Built in 1852, the Mountain House, listed on the national historic register, is southern Oregon's oldest timber-framed house. Adjacent to the house amid lush gardens, the renovated two-story brick stage coach driver's quarters is a cozy, private get-away. Microwave, refrigerator, electric water pot, coffee maker downstairs along with bathroom. Upstairs comfy queen bed, armoire, easy chair, television, and beautiful views from every window!