Cottage holiday rentals in 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.

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 are free!!

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 Rising Tide Oceanfront Cottage- Dog Friendly!

Immerse yourself in the beauty of The Rising Tide Oceanfront Cottage, built in the 1920s, the ultimate beachfront escape. Nestled on the dunes, this inviting retreat offers unparalleled ocean views, a private path to the sand, and a warm, dog-friendly atmosphere—a perfect setting for your next coastal adventure. Start your days with coffee in the sea breeze, unwind in the evening in the private hot tub, and let the tranquility of the ocean serve as the backdrop to your unforgettable stay.

Little House On The Mountain — Spacious Tiny House

Relax and unwind in our custom-built, one-of-a-kind cabin. Nestled on a forested hill above our main cabin, it sits on 4 acres of private wooded land bordering Mount Hood National Forest. The cabin is designed for year-round comfort, including air conditioning for warmer summer days. A perfect getaway for couples looking to spend a romantic weekend in the woods or a home-base for those who are here to enjoy everything Mt. Hood has to offer. Hiking, fishing, skiing are only minutes away!

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.

The Edgewater Cottage #6

This lovely 1930’s cottage has recently been renovated, but still has that cottage charm. Great view of Netarts Bay, comfy queen bed, and modern kitchenette. You’re just a short walk down the stairs to the bay, or you can relax in the beach chairs out front. Guests love the cottage feel and being able to watch the pelicans and herons or catch a beautiful sunset. It is one of two units with a common wall specially sound proofed for complete privacy.

An Oceanfront Cottage Sunset Deck + Whale Watching

Oceanfront cottage in Depoe Bay with panoramic views above Pirate Cove. This charming one-bedroom, one-bath retreat sleeps up to 4 and blends cozy 1930s character with modern comfort. Fall asleep to the sound of waves and wake with coffee on the deck while watching whales, seals, and bald eagles pass by. Just off HWY 101 and close to Depoe Bay’s harbor, shops, and restaurants. Fully stocked with thoughtful amenities, plus a Tesla charger on site.

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.

The Wayfinder

Step into a timeless retreat and prepare to be in awe of the great pacific ocean. Watch eagle soar, whales pass by, seals swim, waves form and break, sunsets, and if you're lucky watch the commercial crabbing vessels brave the open waters. The cottage is a gem with a gorgeous panoramic view. Time tends to slow, bodies relax, and memories are made in this ocean cottage retreat.

Enchanting Ocean Views and Hot Tub at The Burrow

Step out of time and into your bathrobe at The Burrow. The magic and whimsy are yours in this 3-bedroom cottage getaway. Soak away your troubles in the hot tub as you gaze into the vastness of the Pacific. Whether you're on vacation with the family, on a business retreat or a romantic date, there's something here for everyone.

Charming cottage in a peaceful garden setting.

Charming cottage nestled in a quiet garden setting. This cozy one-bedroom space includes parking and wifi. This stand-alone guest house is opposite the owner's home on 16 wooded acres with a creek, and abundant wildlife. Provides easy access to Willamette Valley wineries and local farm stores.