Family-friendly holiday rentals in Jackson County

Riverfront Retreat w/Pool, Hot Tub, Mountain Views

Soak in riverfront & mountain views from the hot tub or private balconies at this luxury 10-acre retreat! 3BR/4BA with 2 master suites, plus a separate pool house with its own bath — sleeps up to 12. Enjoy the pool, gravel paths to the river, and total privacy on the property. Ideal for extended stays (30+ nights) — perfect for relocations, remote work, or seasonal getaways. Interested in a shorter stay or your desired dates aren’t available? Message us directly to check availability and rates.

Family · Indoor spaces · View

The Hygge Stay in the Heart of Southern Oregon

Pet friendly**Close to the I-5 interstate. Within walking distance to park! This guest house, is filled with natural light making it bright and inviting. Thoughtfully designed with guests in mind, you will have no trouble feeling comfortable with all the amenities you’ll need. *Fun fact**, the night stands in the main bedroom were made in the shop downstairs and designed by husband and I! *Airbnb is above working cabinet shop* Message me if you have any questions, I’ll respond within an hour!

Family · Kitchen · Layout

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in primary, living room with a fireplace and an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, & the Britt Pavilion.

Family · Indoor spaces · Hospitality

Starlight Meadow Yurt

The yurt is a modern, light, space with a deck. It's nestled between a mixed conifer forest and Starlight Meadow. We're at the end of a private road on 20 acres. The property is gated for your comfort and peace of mind. There's a large trampoline at the edge of the meadow perfect for stargazing and sunsets. The creek flows October thru June depending on rainfall. Six miles from Shady Cove where you'll find restaurants and a grocery store. 40 miles to Crater Lake. 26 to Ashland. Treat yourself!

Kitchen · Family · TV

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

Kitchen · Indoor spaces · Decor

Enchanted Conestoga wagon on the Applegate River

Reconnect with nature in the breathtaking Applegate Valley while enjoying the comfort of our cozy covered wagon. Take a step back in time and create memories as our ancestors did on the Oregon trail in covered wagons. Escape the hustle and bustle of everyday life & unwind in harmony with nature on the Applegate River. Enjoy the many nature trails that meander throughout the 12 acres on our farm. Say hello to all of the cute furry animals grazing on our pasture. Your adventure awaits!!

Family · Kitchen · Comfort

Beautiful Country Home next to Jacksonville!

The whole group will enjoy easy access to everything from this centrally located home! Enjoy a pool day with the family next to the serine pool. Or a fun day of wine tasting with Relik winery less than one mile away and Hummingbird less than 2 miles away! Or have a blast at a concert this summer at the Britt festival less than 2 miles away! Downtown Jacksonville is only a 3 minute drive! All queen beds have been upgraded to NEW Tempurpedic beds! King size bed is a Jennings (Very High Quality!)

Indoor spaces · Family · Sleep quality

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.

Kitchen · Indoor spaces · Decor

Ripple Rock Lodge- Gateway to Crater Lake

The Ripple Rock Lodge offers amazing views of The Rogue River Gorge and Lost Creek Lake. The lodge has a large patio with ambient lighting, and both gas and charcoal grills! It is located on a 10 acres parcel of woodlands to explore with access to the Rogue River and numerous hiking trails. Medford International Airport is approximately 40 miles from the Lodge and Crater Lake National Park is approximately 35 miles. Now offering as a wedding venue, please message with any inquiries!

Family · Indoor spaces · Comfort

Red Barn in Wine Country

Luxury barn with a rustic feel on "Red Barn Farm" in Southern Oregon Wine Country. Our five-acre micro-farm is situated on the Applegate River exactly between Crater Lake & the Redwood forest. Our lush Applegate valley is a region of 19 artisan wineries. Walk to Red Lily Vineyard tasting room. This farmstay has a river swimming hole, friendly chickens, mini-goats & sheep, and a fire pit to spend dreamy evenings under the stars. Visit Wine Country Farm Stay dot com for more info!

Kitchen · Family · River

Eagle’s Nest Cottage | 40 mins to Crater Lake

Rogue River Retreat enjoy a cozy weekend of unplugging and quality time with loved ones! - 60 minutes to Crater Lake National Park - Riverfront retreat on the tranquil Rogue River - Wake up to breathtaking river views - Lounge in the hammock while watching rafters, ducks, and fish drift by - Play Ping-pong - BBQing on the patio - Fishing off the dock is allowed—please bring your own line and tackle. - Cook family meals together - Play board games - Stream movies on the Roku TV

Kitchen · Family · Access

Golf, Raft, Hike, Relax in Home near Crater Lake

Welcome to the perfect getaway for couples, friends, and families. Located in the peaceful city of Eagle Point, you'll get that small town feel that's near many activities, restaurants, and destinations that Southern Oregon has to offer. Our lovely home borders the Robert Trent Jones designed Eagle Point Golf Course, is located near many beautiful wineries, and is an hour and fifteen minutes away from the infamous Crater Lake.

Indoor spaces · Family · Amenities