Cottage vacation rentals in Southern Oregon

"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.

Wine Country Farm Stay Near Ashland

Stunning romantic wine getaway on a flower farm with spectacular views. Farm stay offers the perfect base for exploring the Rogue Valley wine trail, 15 minutes to over 20 Jacksonville and Ashland wineries in the heart of the valley. Cozy private deck offers a perfect spot to relax and enjoy wine with views of mountains, pastures, and fields. Home of the Oregon Shakespeare and Britt Festivals. One mile from the Greenway, a bike and pedestrian pathway. Enjoy a beautiful ride to local wineries.

Wee Bird Coastal Cottage

This artistically-crafted, coastal cottage provides an uplifting and peaceful space to relax and explore. Located walking distance to beautiful beaches, the local co-op, and several restaurants and bars, this unique cottage offers the perfect getaway for those who want to slow down the pace and lose themselves in stunning coastal beauty. We heartily welcome folks from all backgrounds and walks of life, to come enjoy a slice of artistic heaven along the southern Oregon coast. Pets $15 each

Charming very well appointed cottage !

The Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 1 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If comfort what you are looking for, the cottage will meet all your needs.

Cottage on River Farm -Applegate Wine Trail

Cozy one-room cottage on a 5-acre micro-farm, on the Applegate River near vineyards. Set halfway between Crater Lake & the Redwood Forest, the Applegate Valley is a lush valley with 19 artisan vineyards. This classic cottage is a mini farm-stay experience with goats & chickens. Walk to Red Lily Vineyard! Enjoy the private firepit with complimentary s’mores kit or walk down to the river to swim. Nearby: the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival.

Rogue River Retreat

Located on the Upper Rogue River, this riverfront cottage is perfect whether you seek a quiet weekend away or fishing for steelhead, (plus, there's a great run right in front of the cottage). We're just down the way from the Riverhouse and bridge, close to town. It is a very quiet and serene atmosphere, perfect for unwinding. The geese will wake you up in the morning and the deer and raccoons will amuse you. Feel free to pick fruit from the trees if in season. Sorry, no children.

The Old FarmHouse

The Old Farmhouse is just 5 minutes away from the Crater Lake National Park boundary. This is about as close as you can get to Crater Lake short of staying in the park at the lodge. (Note it is another 20-25 minutes of driving through the park to get to the top of the rim.) The Farmhouse is situated by open pastures and with an unobstructed view to the Cascade Mountain Range. Enjoy cooking in the full kitchen, or unwind with a game pool. Enjoy your Crater Lake Country stay.

Efficient, clean, pet-friendly 2 bed/bath cottage

Our 2 bedroom 2 bath guesthouse is a gem! Located in a quiet neighborhood in SE Medford with a garden and spacious back deck you'll be just a few minutes from downtown, both local hospitals, and the airport with easy access to the freeway. This home is just 20 minutes from downtown Ashland and Jacksonville. A great spot for families. Well-behaved pets welcome! *We sanitize commonly touched surfaces after each booking and comply with Airbnb's enhanced cleaning procedures*

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.

Cozy Spring Creek Cottage

Cozy, pet-friendly cottage near Crater Lake National Park, Diamond Lake, and the Klamath Basin! This comfortable 2-bedroom retreat is the perfect basecamp for adventure, wildlife viewing, remote work, or a relaxing getaway. Enjoy a fully stocked kitchen, BBQ, fireplace, and high-speed internet. Guest kayaks and a dock on beautiful Spring Creek are shared with our neighboring cabin. Watch for eagles, ducks, and other wildlife during your stay!

Cozy Home w/River Access, Hot Tub, 7min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.