Holiday rentals in Mount Ashland

Cozy Family Ranch Cottage! Near Vineyards & Lake!

Welcome to Guches Ranch! Nestled on a picturesque ranch established in 1964 by the Guches family, a vast expanse of lush farmland. Our Airbnb listing is the ultimate retreat for those seeking solace and serenity away from the hustle & bustle of city life. We are located centrally to local popular Vineyards in the serene Applegate Valley, just 12 miles outside the historic Jacksonville Oregon. Our brand new modern-style single cottage is a stand alone unit & is a private cozy, yet spacious haven.

Peaceful Forest Cabin w/Cedar Hot Tub

Soak in a gorgeous cedar hot tub surrounded by forest. A quiet gem in the Siskiyou foothills, 15-20 min from Ashland’s Shakespeare Festival and Rogue Valley wineries. This craftsman tiny cabin sits above a seasonal creek with decks on two sides. Cozy loft bedroom, warm interiors, simple kitchenette. Wagner Creek trails steps away. Deer, turkeys, and occasional black bears visit. Eco-friendly throughout. Your restorative retreat awaits. We live on-site and love hosting but give you your space.

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

Wine Country Farm Stay Near Ashland

Stunning romantic wine getaway on a flower farm with spectacular views. Farm stay offers the perfect base for exploring the Rogue Valley wine trail, 15 minutes to over 20 Jacksonville and Ashland wineries in the heart of the valley. Cozy private deck offers a perfect spot to relax and enjoy wine with views of mountains, pastures, and fields. Home of the Oregon Shakespeare and Britt Festivals. One mile from the Greenway, a bike and pedestrian pathway. Enjoy a beautiful ride to local wineries.

Charming very well appointed cottage !

The 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 1 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 comfort what you are looking for, the cottage will meet all your needs.

Mountain Greens Cabin

Looking for a peaceful getaway?🌲Welcome to Mountain Greens Cabin! Enjoy a relaxing stay at this unique & tranquil cabin right in the beautiful forest of Southern Oregon. You will feel right at home in this cozy cabin with scenic Mountain views. Conveniently located right off the freeway, only 10 miles from Grants Pass! Enjoy your own private nature walk, where you can view wildlife right from the cabin! After exploring, you will feel relaxed and comfortable the moment you enter the cabin!

The Birdhouse Retreat| Views & Hot Tub

Take it easy at this unique and tranquil getaway. Immerse yourself with the sound of the forest gazing at the Applegate valley and lavender farms below. Walk around in over 10 acres of forest and enjoy a forest bath and sounds of the river below. Minutes from renowned Applegate Valley wineries and Applegate lake. Snow capped mountains in view most of the year. This space has a private bedroom and bathroom with a separate entrance. For the chilly nights, enjoy a cozy fireplace and a movie.

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. NEW: a high speed (240 volt) charger for EVs. You need an adapter.

Cabin Serenity at Applegate Winery

Escape to your own cozy cabin, tucked away in a private wooded forest on a stunning vineyard & winery. Perfect for a quiet & peaceful getaway! Wake up to forest views from your king bed or unwind with a glass of wine on one of two private decks. Located at Walport Family Cellars in the heart of Applegate wine country, with 18+ wineries nearby—many within walking distance! For guests over 21, enjoy honorary wine club perks, including complimentary flights and purchase discounts!

Vineyard Cottage-Winery, Hot Tub, Privacy

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.

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.