Cottage holiday rentals in Southern Oregon

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Southern Oregon

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Ashland

4.95 out of 5 average rating, 420 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.

Superhost

Cottage in Fort Klamath

4.83 out of 5 average rating, 188 reviews

Cozy Cottage Close to Crater Lake

The cottage is a cozy suite for two for a romantic getaway or a quiet night in the country. The property has a large lawn area with picnic tables and firepit for watching the stars and cooking s'mores. Our Cottage is the perfect size for two. It features a king size bed and two swivel chairs for relaxing as well a table for eating or working. The kitchenette has a microwave, sink, and mini-refrigerator, as well as a Keurig Coffee maker, toaster and dishes for two. There is also a bbq supplied.

Guest favourite

Cottage in Chiloquin

4.95 out of 5 average rating, 145 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 favourite

Cottage in Central Point

4.98 out of 5 average rating, 455 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 McKenzie Bridge

4.93 out of 5 average rating, 112 reviews

Cascadia Cottage-Riverfront near HotSpring& Hoodoo

Hit the hot springs on your way home from skiing! Retreat to the land of big trees, ferns, and the McKenzie River. The cottage is situated on an acre of riverfront property, with 3 bedrooms, 2 baths, and a covered porch that is ideal for drinking coffee and taking in the river views. The home is equipped with a large kitchen and dining room to host family-style meals and gatherings. Whether you’re here to ride singletrack trails, raft the river, or spend quality time with family and friends.

Guest favourite

Cottage in Pleasant Hill

4.92 out of 5 average rating, 197 reviews

Shepherd’s cottage

Our charming two bedroom cottage enjoys a rustic and peaceful location. Enjoy nature with walks on our organic farm and biking on nearby routes. Scenic rivers, lakes, and historic covered bridges are just a few miles away. We are close to several parks, hiking trails through the woods and a free public disc golf course on Dexter lake. Access to ski resorts and winter sports, natural hot springs are an hour away in the breathtaking Cascade mountains. Fully updated for comfort and relaxation.

Top Guest favourite

Cottage in Klamath

5 out of 5 average rating, 498 reviews

Hunter Creek Cottage

The Hunter Creek Cottage is located in Klamath, Ca. Where the mouth of the Klamath River meets the Pacific Ocean in the heart of the Redwoods. The cottage has three bedrooms, one bathroom and sleeps 6 comfortably with 1 king, 1 queen and 1 double bed. Our cottage is known for being clean, comfortable and memorable. 7 minutes from the ocean, Klamath River and Trees of Mystery. Come enjoy hiking, fishing and relaxation. High speed internet included for distance learning or streaming for work.

Top Guest favourite

Cottage in Bend

4.99 out of 5 average rating, 119 reviews

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

Top Guest favourite

Cottage in Ashland

4.93 out of 5 average rating, 232 reviews

Weisinger Winery Vineyard Cottage

Our vineyard cottage is located at Weisinger Family Winery in Ashland, Oregon. Built c. 1920, our vineyard cottage was the original farmhouse on the property and was recently remodeled in order to encompass the amenities and comforts of home. The hot tub and BBQ on the deck overlook our Pinot Noir vineyard. The property has wonderful views and privacy. A complimentary bottle of wine, cheese, and crackers are awaiting your arrival along with a free tasting in our tasting room.

Guest favourite

Cottage in Coos Bay

4.93 out of 5 average rating, 201 reviews

Bay Cove Cottage A

On the Bay across from Charleston Harbor. Bright, clean, and cozy, rustic 1940s era cottage duplex, perfect for frugal travelers. Features kitchenette, comfortable queen bed plus fold-out sofa bed in the living room. There is no view from inside the cottage, but a small patio with fire pit (weather permitting) is available with gorgeous views from outside the cottage. Cottage A is close to Cape Arago Hwy., and receives more road noise than any of our other properties.

Top Guest favourite

Cottage in Port Orford

4.99 out of 5 average rating, 182 reviews

Ridgecrest Cottage Spa & Fire Pit

Ridgecrest Cottage is located on a hillside with a ocean view in the beautiful small coastal town of Port Orford Oregon. Ridgecrest Cottage is a 2 story 1,600 sq ft house connected by and exterior staircase. It is a 2 bath 2 bedroom and has a sleeping loft with two additional beds. The yard is fenced in and has an additional outdoor dog kennel if needed. There is a Hot Tub, fire pit, gas grill, herb garden, & plenty of outdoor seating.

Top Guest favourite

Cottage in Bend

4.97 out of 5 average rating, 119 reviews

Exceptional Downtown Cottage-Level II EV charger

24 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" Exceptional 5 Star reviews for all vacation rentals in the Bend area. The Cottage is constantly being updated including new furniture, appliances, paint, and even painting of the cabinets. These significant investments keep the Cottage fresh and like it was brand new. City of Bend Short Term Rental Operating License: STR-20-0285