Cottage holiday rentals in Southern Oregon

Cape Cod Cottages #7 - Oceanfront with Fireplace!

Experience the magic of the Oregon Coast in this freshly renovated oceanfront duplex cottage with gas fireplace, perfectly positioned on pristine Big Stump Beach. Step outside your door onto miles of sandy shoreline, where the rhythmic waves and coastal breeze create the perfect backdrop for your beach getaway. Inside, you'll find a thoughtfully updated interior featuring a fully equipped kitchen with modern amenities, including a dishwasher for effortless cleanup after seaside meals. The cottage accommodates up to four guests with a king bed in the bedroom and a full size sleeper sofa in a cozy TV nook off the living room. The covered oceanfront deck allows you to take in the sounds of the ocean while staying protected from the weather. The gas fireplace adds to the warm and inviting atmosphere throughout your stay. Your Perfect Base for Coastal Adventures: North to Waldport (minutes away): Dive into authentic coastal activities like crabbing from Dock of the Bay or McKinley's Oregon Coast Marina. During low tide, try your hand at clamming near the bridge. South to Yachats (just a few miles): Discover charming restaurants and explore remarkable rocky tidepools along the dramatic coastline. Further Explorations: Visit the fascinating Newport Aquarium (30 minutes north) or embark on an adventure at the Sand Dunes (45 minutes south) - accessible by foot, ATV rental, or guided tour. Traveling with a group? Cape Cod Cottages features eight additional units on the property, perfect for family reunions or friend gatherings. Shared amenities include: 300 feet of private beach access Entertainment-ready game room featuring foosball and ping pong Free guest laundry facilities Three EV charging stations

"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.

Riverfront Cottage near Loloma/Hotsprings/Hoodoo

From the deck, listen to the Mckenzie River rapids while osprey & eagle soar above. Cozy cottage is right on the banks of the Mckenzie River! Walking distance to local pub, general store & grill in Mckenzie Bridge. 2 min drive to Loloma Lodge & 5 min to Tokatee Golf. 15 min drive east or west to Belknap or Cougar Hotsprings. A stretch more to Proxy, Sahalie & Koosah waterfalls, Blue Pool, or Hoodoo Ski Area. Trails, mountain biking, golf, snow shoes, skiing, rafting, fishing - adventure awaits!

Romantic Barn Guest House Quiet & Coastal

Barney’s Guest House is a private, stand-alone barn retreat offering peace, privacy, and easy access to S. OR stunning coastline. Thoughtfully remodeled and exceptionally quiet, it’s ideal for couples or solo travelers looking to unwind just minutes from Samuel H. Boardman State Park, Brookings, and Gold Beach. Pets may be accepted with prior approval; pet fees apply. Long-term stays and cleaning fees must be arranged in advance. Instant Book is not available for weekly or monthly reservations

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.

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

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

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.

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.

Wild Coast Lookout

Perched on an ancient sea stack above the Oregon coast, Wild Coast Lookout offers a rare blend of privacy, dramatic views, and easy access to the beach. Soak in the hot tub while watching the sunset or under a sky full of stars, listening to the surf below. You can also wander the lower garden's brick path, finding a peaceful spot to unwind and enjoy the feeling of your own coastal retreat.

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.