Cottage holiday rentals in Southern Oregon

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Top-rated cottage rentals in Southern Oregon

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Glendale

4.92 out of 5 average rating, 296 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 favourite

Cottage in Azalea

4.94 out of 5 average rating, 161 reviews

Blissful Solitude - Sweet Cottage

Perfect Pandemic Getaway! Walk in the woods, photograph nature, meander in the meadow, picnic creekside on a peaceful platform. Read, write, relax w/ a glass of wine in our woodsy wonderland! Our sweet cottage has it all for a cozy stay: living space, bedroom, a great hot shower, kitchen to cook a savory stew. Stay in our Beautiful Sanctuary & wake up to the skylight above the comfy Tempurpedic bed. A special place for Precious downtime. Also available/Book w/ friends: search "Orchard House"

Guest favourite

Cottage in Ashland

4.96 out of 5 average rating, 371 reviews

Charming very well appointed cottage !

The Farm 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 2 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 quiet is what you are looking for, the cottage will meet all your needs.

Guest favourite

Cottage in Port Orford

4.96 out of 5 average rating, 729 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!

Guest favourite

Cottage in Chiloquin

4.83 out of 5 average rating, 210 reviews

River Haven Cottage

This is a cute little cottage built in the 1930's on the Williamson River. Down river, there are trout in it for fishing, catch and release only, anyone over 12 must have a license to fish. The deck at the back of the house is partially covered. The river is also great for playing, swimming (a little cold in spring) and for kayaking. There is a kayak rental store in town. The air is usually warm, 70's & 80's, on summer afternoons. There are stairs to enter the cottage. Great place to relax.

Guest favourite

Cottage in Central Point

4.98 out of 5 average rating, 401 reviews

Country Garden Cottage

Newly remodeled Garden Cottage with living area/kitchenette, bedroom, and bathroom. Cottage has high ceilings, ceramic tile floors, quartz countertop, cherry wood cabinets and new mini-split heater/air conditioner. It is bordered on two sides by a garden common area with seating, fountain, and a grape vine covered pergola. New Roku TV installed. Conveniently located: * 5 min to I-5 * 10 min to airport * 3 min to Central Point * 10 min to Medford * 5 min to Jacksonville * 25 min to Ashland

Guest favourite

Cottage in Myrtle Creek

4.99 out of 5 average rating, 121 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 favourite

Cottage in Roseburg

4.99 out of 5 average rating, 230 reviews

Bella's Cozy Cottage, Entire home with yard use

Our reviews say it all! We are guests favorite/super hosts. This sweet little 40's cottage is cozy and full of charm & period pieces.Just 1/4 mile off I-5 in a nice, quiet neighborhood. Very close to VA, bike path, shopping CTR, grocery stores ( Fred Meyers,Grocery Outlet), coffee, restaurants & fast foods. Close to Mercy Hos. Great location for day trips to the Oregon Coast, Crater/Diamond Lakes, fishing, boating, Umpqua Valley Wines, Golfing, WildLife Safari & more

Guest favourite

Cottage in Grants Pass

4.96 out of 5 average rating, 201 reviews

Applegate Wine Country cottage!

Our "Lil Wanderer" cottage is 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 on site opening in summer 2024! Also, with 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport,Troon, Schmidt, Blossom Barn, Rosellas & Solaro just to name a few. Downtown Grants Pass & Jacksonville are 30 minutes away.

Guest favourite

Cottage in Sutherlin

4.97 out of 5 average rating, 187 reviews

Wayside-centrally located, super convenient!

The convenience of a hotel with the feel of home. Wayside is a renovated 1950's cottage. Playfully retro yet modern where it counts with fast wifi, updated kitchen & bath and smart lock for hassle free check-in. Less than 1/2 mile to I-5 & the largest EV charging station in Oregon, walking distance to food & shopping but with a fenced yard for privacy! Full kitchen with coffee/tea station, washer/dryer, & comfy beds. Off street parking in extra long driveway.

Guest favourite

Cottage in North Bend

4.97 out of 5 average rating, 133 reviews

Cottage on the Bay

Monthly rates available! Cottage style decor with shabby chic and slip-covered furniture. We are 3-1/2 miles from the North Bend (McCullough) Bridge and only about 5 miles from the nearest beach, Horsfall Beach, and the famous sand dunes. This is our guest house, but you will enjoy plenty of privacy in this quiet little cottage. You may also enjoy your large private deck and flower garden that we've created for your enjoyment.

Guest favourite

Cottage in Gold Beach

4.97 out of 5 average rating, 380 reviews

Windsong Garden Cottage

An affordable garden-view cottage, close to beaches and Rogue River. Charming, peaceful, ideal for a couple seeking a quiet coastal getaway. A woodland backdrop and garden views surround. The outdoor clawfoot soaking tub is a Guest Favorite! The hosts' chickens provide fresh eggs and friendly morning wake-up call. Hosts provide special 'extras' for a truly memorable visit.