Orlofseignir í Ashland

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.

Ashland Zen Den

Brand new remodeled and designed downstairs basement apartment on Main St. in Ashland. This modern space is clean and peaceful. Each bedroom is equipped with high end mattresses, linens, TV, and bath robes. There are plenty of books to read and board games to entertain. Enjoy a short walk to downtown where you will find Lithia park, restaurants, cafes, and shopping! 25 min. drive to mt Ashland and world class MTB. Walking distance to Shakespeare festival. Plenty of beautiful wineries near by!

Peaceful Forest Cabin w/Cedar Hot Tub

Welcome to our cozy cabin, nestled in Oregon’s lush forest beside a seasonal creek. Blending rustic craftsman charm with a bohemian flair, our cabin provides a warm ambiance with a well-equipped kitchenette , living room, and a walnut bar-top dining area. In the mezzanine loft, find an organic queen bed and a workspace with a fold-out futon. Enjoy our wood fired hot tub, Wagner Creek trails, nearby wineries and the Shakespeare festival, offering a mix of nature’s beauty and local culture.

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

Affordable Luxury- One block to Downtown

Welcome to The Matriarch, a historic heritage property in downtown Ashland. This self check-in style accommodations for our Suite 2, means you have the place all to yourself. Stroll to dinner at one of Ashland's finest restaurants or cozy up in the private outdoor living room. Expect thoughtful local touches and attention to every last detail. Soak in the beauty of bold design as you decompress in the large king bed. The Matriarch is our newest addition to the Swank House family.(#18-243)

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. Charging is available for your electric cars in the upper parking area.

C Street Station Cottage

Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

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.

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

Creekside Retreat Close to Town

You will be a 10 minute drive from Downtown Ashland and feel like you are out in the country. The home sits on 8 private acres and has river frontage and a beach on the year round Emigrant Creek. There are beautiful views in all directions of mountains, trees and wildlife. The home is a two story residential barn built in 2012 and remodeled in 2022 (the main living quarters is upstairs).