Family-friendly holiday rentals in Douglas County

Crater Lake "Meadow House" near south entrance.

One of closest to Crater Lake (28.9 miles), Rogue River, Lost Creek Lake, 3 waterfalls, +100 ranch acres of woodland trails. Upscale creature comforts; 2-story, 2500 sq. ft., fully-renovated historic ranch home: hardwood floors, fireplace, large kitchen, 2 bedrms w/2 private baths +an xtra small sleeping room, views of mtns & meadows are spectacular. Enjoy the ranch & wildlife relaxing on wrap-around deck. Perfect for couples, small getaways & sm families (kids over 10),or a work away. No pets

The Cottages at Porter Hill (Green)-Near Roseburg

Welcome to The Cottages at Porter Hill, nestled in the heart of Umpqua Valley Wine Country. A perfect retreat for two! This cozy 1 bedroom cottage is inspired by the green fields of central Italy & simple country living. We invite you to slow down, relax and experience our little slice of heaven! Conveniently located on Highway 42 with easy access to Winston, the Wildlife Safari and Roseburg (10 - 15 minutes) to the east and the Oregon coast-Coos Bay and Bandon (just 1.5 hours) to the west.

Bailey River House

Spacious 3 BR 2 bath. The primary bedroom has a king bed. The other 2 rooms have queen beds. The extra bonus room has 2 cots, full sofa sleeper and a Queen platform bed. The home is fully stocked with EVERYTHING you need. NO PETS and NO SMOKING inside the home, especially Marijuana. There will be a $100 -$200 fee if this rule is broken. PARTIES & EVENTS are not allowed until further notice. Airbnb has a global ban of no more than 16 people allowed on the property. Outside cameras in use.

The Hippie Shack Yurt +Tiny House + Farm Breakfast

This elegant 24-ft cedar-lined yurt features hardwood floors, heat, A/C, queen bed & queen futon. Open and airy with a clear dome to stargaze from bed! A private attached tiny home includes a bathroom with hot shower and a full kitchen with propane stove, fridge, coffee maker (no microwave). Free continental breakfast: croissants, jelly, yogurt w/ fruit, oatmeal, juice, coffee & tea. Private farm setting near river, animals roam outside. 15 min to Canyonville, 40 min to Safari. Organic farm !

The Bliss/100% privacy/AC/game room/2 blks 2 DT

Welcome to The Bliss, a charming studio-style guesthouse, designed for relaxation, comfort, and a little bit of magic. Tucked quietly behind our home, this private retreat offers the perfect blend of rustic character and chic style—just two blocks from downtown. Whether you’re here for a weekend escape, wine tasting, or a peaceful reset. The Bliss is a place where guests instantly feel spoiled, relaxed, and well cared for. Waterfalls, (1 hr)Crater lake (90 min)Wildlife safari (10 min)

Highway to Diamond Lake/Crater Lake roadtrip stop!

Relax and have some fun in our renovated 1 bed/1 bath detatched garage in our large fenced back yard. The space can sleep 6 people with a queen size bed, with queen and full size futon/sleepers. One block off highway 138, within minutes of a coffee shop, 3 restauraunts and a bar and grill. Single serve coffee maker, electric skillet, microwave, and a mini fridge. Pool/ping pong table, 55" smarttv, preloaded Nintendo, bluray player, and board games. Ask for wifi😊

Umpqua Valley Garden Getaway

Minutes from several award-winning wineries and local fishing holes, the Umpqua Valley Garden Getaway has all the amenities you will need for a memorable vacation. Down a cobblestone stairway, you will find a pristinely redesigned cottage nestled in a private backyard garden. Start your day with a hot cup of coffee from the wicker chairs overlooking the backyard and end your day dining al fresco as string lights dangle above a cozy corner of the deck.

Lavish Country Retreat studio

Escape to our peaceful 9-acre farm in the southern Willamette Valley, surrounded by fresh air, nature, and the sound of nearby rivers. This 590 sq ft attached private studio suite features a cozy queen bed, pellet stove, kitchenette, full bath, & a private fenced backyard with patio seating and pasture views. Pet- and kid-friendly with a private keyed entry and free front-door parking—your perfect countryside getaway awaits.

Chardonnay Chalet at the Vineyard

Enjoy the ultimate Pacific Northwest getaway in our luxury vineyard guest house. We are perfectly located as a launching point to experience Ocean Beaches (1.5 hours), Crater Lake National Park (2.5 hours), Waterfall Hikes (45 minutes), and Wine Tasting (a 5 minute walk!) Enjoy the view from the elegant patio while cooking/grilling, take a stroll through the vines, or a hike up the hill to enjoy the view from the hammocks.

Highlands and Horses Ranch Airbnb

Meet friendly Highland Cows and beautiful horses on a lush green ranch nestled in rolling hills. Just 13 miles east of I-5, this peaceful retreat offers total nature immersion. Even the drive delights—with farms, grazing sheep, and scenic views at every turn. Step out, breathe deep, and let the fresh country air melt your stress away. It’s more than a getaway—it’s a soul-refreshing retreat!

Lone Wolf Cabin, pet friendly

Lone Wolf Cabin is situated on a gated road in a forest setting. It is the only residence on the road. It is about 2 miles from both Oakridge and Westfir which makes it convenient for mountain bike riding, hiking, golfing and dining out. There are both Forest Service Trails and game trails near the cabin. The cabin is rustic with modern conveniences. Weekly discount is $500.00

Urban Boho Charmer! 2 Bdrm 1 Bath Fire pit table

Urban Boho Style comes to Roseburg! Open for long or short term stays, the Charmer arrives as a favorite addition to Superhosts, Paul & April. The charmer welcomes you to the comfortable collections of textures & fabrics dotting natural colors. From our persian rugs to our rattan swing, you'll feel like this is your true retreat as you enjoy your stay.