Cottage vacation rentals in Southern Oregon

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Top-rated cottage rentals in Southern Oregon

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Guest favorite

A spacious bedroom features a large bed dressed in neutral-colored linens, complemented by decorative pillows. Natural light enters through sliding glass doors, illuminating the warm hardwood floor. A bedside table with a lamp adds functionality to the cozy space.

Cottage in Glendale

4.91 out of 5 average rating, 351 reviews

★ Cowcreek Cottage off of I5★

A comfortable 2 bedrm a 𝐍𝐎𝐍 𝐒𝐌𝐎𝐊𝐈𝐍𝐆 home on 13 acres, all self-contained. All new major appliances. Peggy has made the kitchen a "cook's kitchen", to make cooking easy.We have added a pizza stone and Pizza paddle. The 1st bedrm has a king bed, the 2nd bedrm has 3 twin beds and a full sized bed. You have access to cow creek and our two ponds, We have kayaks and SUP paddle board for our guests and life vest all sizes. Hiking trail by Cow Creek, Tables &chairs 4 you camera at driveway entrance

Guest favorite

A welcoming cottage exterior is framed by greenery, featuring a charming front porch with seating and flower pots. A gravel pathway leads to the entrance, which has a bright front door and decorative elements enhancing the inviting entrance.

Cottage in Grants Pass

4.96 out of 5 average rating, 255 reviews

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.

Guest favorite

A cozy blue cottage is presented with a welcoming front porch and a light pathway leading to the entrance. Large windows allow natural light to brighten the interior. The lush green lawn contrasts with the vibrant exterior, while the water and trees create a serene backdrop.

Cottage in Coos Bay

4.98 out of 5 average rating, 527 reviews

"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.

Top guest favorite

A cozy bedroom features a spacious bed adorned with a quilted cover and decorative pillows. A wooden tray with two mugs, a plate with snacks, and a small vase of flowers rests on the bed. Light streams in through two windows, highlighting the calming decor.

Cottage in Tenmile

5 out of 5 average rating, 106 reviews

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.

Guest favorite

The exterior of the cottage is showcased, featuring a welcoming porch with a sitting area. An American flag is displayed prominently, and the surrounding greenery includes several trees and blooming plants, contributing to a peaceful rural setting.

Cottage in Chiloquin

4.96 out of 5 average rating, 161 reviews

Cozy Spring Creek Cottage

Kayaks, internet and nature! Basecamp for Crater Lake, Diamond Lake & the Klamath Basin! Make some memories at this clean, cozy, family and pet friendly 2 bedroom cottage. Kitchen & BBQ are fully stocked and this well appointed living space is a perfect place to relax after a day outside or for remote work! Curl up by the fire in the evening or head out to town! This cottage is in the forest near Spring Creek for kayaking. Enjoy the dock from that is shared with our cabin next to the creek!

Top guest favorite

An open living space showcases a high, wooden-beamed ceiling and a cozy dining area with two barstools. Natural light filters through multiple windows, illuminating the eclectic decor, including surfboards and artwork. Potted plants add a touch of greenery to the inviting atmosphere.

Cottage in Port Orford

4.96 out of 5 average rating, 871 reviews

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 STAY FREE!

Top guest favorite

A scenic view from a covered porch captures the sunset over Lake Euwana and surrounding mountains. Lush greenery frames the vista, with a glimpse of residential structures visible in the foreground.

Cottage in Klamath Falls

4.99 out of 5 average rating, 140 reviews

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!

Top guest favorite

An open living space features a comfortable gray sofa adorned with two yellow cushions. A wooden coffee table rests on a colorful area rug, and the kitchen area showcases white cabinetry. Bright light enters through windows and a glass door, leading to a private outdoor area.

Cottage in Phoenix

4.99 out of 5 average rating, 443 reviews

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.

Guest favorite

The classic cottage is framed by green foliage, showcasing a welcoming entryway with a black door and a symmetrical window. A bench is positioned on the porch, complemented by flower pots on either side. The gravel path leads to the entrance, surrounded by trees.

Cottage in Jacksonville

4.91 out of 5 average rating, 207 reviews

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.

Top guest favorite

The tranquil Upper Rogue River is captured, reflecting a vibrant blue sky. Lush green trees line the riverbank, with a distant view of a cottage nestled among the foliage, creating a serene and natural setting.

Cottage in Shady Cove

4.99 out of 5 average rating, 117 reviews

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.

Top guest favorite

Two goats rest together on a colorful welcome mat located at the entrance of the cottage. The door behind them features multiple panes of glass framed in a vibrant turquoise, creating a cheerful focal point for the scene.

Cottage in Myrtle Creek

4.98 out of 5 average rating, 165 reviews

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).

Guest favorite

An outdoor hot tub is illuminated under warm string lights, set within a wooden gazebo. The surrounding area features wooden fencing and lush greenery, creating a serene environment. A soft blue glow from the water contrasts with the warm evening sky, enhancing the tranquil ambiance.

Cottage in Jacksonville

4.94 out of 5 average rating, 421 reviews

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.