Cottage vacation rentals in Crater Lake

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.

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.

Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

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.

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!

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

Great View | Gateway to Crater Lake | Fall prices

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!

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.

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.

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).

Efficient, clean, pet-friendly 2 bed/bath cottage

Our 2 bedroom 2 bath guesthouse is a gem! Located in a quiet neighborhood in SE Medford with a garden and spacious back deck you'll be just a few minutes from downtown, both local hospitals, and the airport with easy access to the freeway. This home is just 20 minutes from downtown Ashland and Jacksonville. A great spot for families. Well-behaved pets welcome! *We sanitize commonly touched surfaces after each booking and comply with Airbnb's enhanced cleaning procedures*

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.