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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.

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.

Little Elk Lodge

Charming cottage, decorated in an cozy lodge style, located just off Main Street in the beautiful little historic town of Ft. Jones. Located next door to The Trading Post, a small cafe with great espresso, fresh baked goodies & gourmet sandwiches, & within walking distance of fabulous museum, tavern & restaurants, art gallery, bank, post office, library, etc.. Full kitchen, free parking & wifi. Pet friendly. Enjoy scenic outdoor pursuits locally, such as hiking, fishing, cycling & more!

Amazing View | Gateway to Crater Lake

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!

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.

Kidder Creek Cottage, In the heart of Scott Valley

Kidder Creek Cottage is a tranquil getaway in Scott Valley, the gateway to the Marble Mountains. Kidder Creek trailhead is just up the road. Outdoor opportunities abound, including cycling, hiking, and fishing. The area has many scenic and winding roads perfect for the avid motorcyclist. There are a number of local restaurants and breweries to explore, all within your reach. You'll enjoy the quiet atmosphere and beautiful starry nights. This custom cottage is a one of a kind getaway.

Tranquil Remodeled Cottage w/ Private Creek!

Recently remodeled and tastefully furnished, this relaxing cozy cottage boasts a unique charm with your own private creek running though the property! The creek runs along the backside bedroom and continues under the dining room of the actual home! Built in 1912, our home has all the charm of yesteryear with the all amenities you need in this decade. If you are looking for a relaxing mountain getaway with easy access to restaurants & outdoor activities then this is the spot.

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.

Happy and cozy one-bedroom cottage that sleeps 4.

The Blue Haven, located in the friendly Gateway Community is the perfect place to rejuvenate and unwind. Kick back and relax in this calm, stylish space with all new amenities. The kitchen is fully equipped and prepped to make any meal. The firm queen bed and firm pull-out sofa are extremely comfortable with cooling mattress toppers and pillowcase covers. It is a 4-minute drive from downtown, a quarter mile from the headwaters, and .2 miles walk to the Peace Garden.

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.

Sweet Breeze Bungalow

Charming Alley bungalow in the historic railroad district. Walk score of 93. Immerse yourself in the heart of Ashland. 5 min. walk to downtown, an easy 8 min. walk to Shakespeare & Cabaret Theaters. Walk to pubs, restaurants, coffee shops, spa's, markets, movie theater, Lithia Park, Japanese garden and trailheads all within 5-12 mins. Nice bike ride to wineries 15 min away, or a 30 min. drive to Mt. Ashland for skiing, hiking, biking and more adventures.

Magical Faeryvale! Walk downtown-Ski Park OPEN!

Ski Park is OPEN! Faeryvale is a magical 120 year old cottage, just right for couples and small families. Nothing fancy but very cozy with a relaxing backyard. License # STR-ALPN108 The view of the Mountain from the backyard looks AMAZING! ADDED VALUE: 14% Tourist Tax included. A licensed listing & we won't ask for more $! Faeryvale is located in town, near shops, restaurants, and our natural foods market, right across the street.