Cottage holiday rentals in Southern Oregon

Applegate cottage at boutique winery!

Located right in the middle of Southern Oregon wine country. You will be staying in a cottage on a vineyard with our own winery and tasting room onsite. Tasting room open Saturday & Sunday. (April-December) With 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport, Troon, Schultz, Schmidt, Blossom Barn, Rosellas & Solaro just to name a few. Downtown Grants Pass & Jacksonville are 30 minutes away. Highway 5 is 30 min away.

"Uncle Joe's Place" Cozy Cottage with Water View

Uncle Joe's Place is a cozy cottage that sits close to the water with views of Charleston bridge and South Slough Estuary. Cottage is 490 square feet, perfect for singles or a couple visiting the area. Located just off Cape Arago Hwy and the town of Charleston. It's a short walk to convenience stores, restaurants and the Charleston Marina. Neighborhood is made up of small homes and mobile homes. Check yourself in with a lockbox. I'm very close by if you need any assistant or have questions.

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.

Gateway to Crater Lake | Amazing View

Quiet, relaxing, newly renovated cottage built in 1906. - Conveniently located near downtown, just off of highway 97 for easy in and out hotel-like access. - Walking distance to the downtown shops, bars, and restaurants. - Enjoy sunsets, moonrises and more with scenic views of Lake Euwana and the nearby mountains as the backdrop from the giant picture window inside or outside on the covered porch. - Just a short walk (or biking) distance to the historic Link River and Eulalona trails!

Modern Getaway on Sunflower Farm

Stunning modern getaway on a flower farm with spectacular views. Nestled in the heart of the valley. 15 minutes from Ashland and Jacksonville. Home of Shakespeare and Britt Festivals. Over 6 wineries and a distillery within a 3 mile radius. Bright design with beautiful features. The many windows and French doors offer light in all directions with views of sunflowers, pear orchards and Roxy Ann Peak. One mile from the Greenway, a bike and pedestrian pathway linking Central Point to Ashland.

Cottage on River Farm -Applegate Wine Trail

Classic one-room cottage on a 5-acre micro-farm, on the Applegate River near vineyards. This cozy cottage is a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit (when not in wildfire season) with complimentary s’mores kit or walk down to the river and breath. We are 15 minutes from the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival. Wine Country Farm Stay dot come.

Rae of Sunshine Sanctuary

Come and enjoy a quiet and relaxing stay where you can put your feet up and unwind inside of our beautiful 100 year old quaint cottage, or enjoy the gorgeous private scenery and wildlife surrounding it. Many which include a variety of birds, deer, our residential goats, pig, horses, bunnies, and our seasonal pond with mallards and frogs. (All of our animals are located on the property but are separate from the cottage. Please see host about scheduling any interactions).

Romantic Retreat w/ Hot Tub & Starlit Massage Room

The Applegate Spa is a top-rated romantic retreat in Southern Oregon’s stunning Applegate Valley. Perfect for couples, it features a private hot tub, cozy fireplace, and a dreamy massage room beneath a glowing starlight ceiling. Surrounded by vineyards, rivers, and charming wineries, this peaceful escape blends rustic charm with comfort and relaxation. Just minutes from historic Jacksonville and scenic trails, it’s the ideal place to unwind, explore, and reconnect.

Ocean Front Cottage w/Hot tub

Ocean front 2b/1b cottage with views of Cape Blanco & Mt. Humbug. Enjoy watching the Sea Lions & Whales from the hot tub or back porch. The home includes a fully stocked kitchen & bathroom, game room, & hammock. Walking/Hiking trails & beach access 1.1 mile from the front door. Smart TV, workout equipment, usb charging stations & desk workspace. Perfect for a couples get away or family vacation.