
Places to stay near Mt. Ashland Ski Area
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Top-rated holiday rentals near Mt. Ashland Ski Area
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Charming cottage, walk to town.
Our guests arrive at The Ashland Cottage and their first words are almost always the same: "It's gorgeous!" That's because the cottage delivers what Ashland visitors want- comfort, charm and a walkable location just 10 minutes from downtown and OSF theaters. Though newly built, the cottage echoes the Craftsman character of our 1920s main residence. As a fully separate house with its own private entrance, it offers spacious living with high ceilings, abundant natural light and inspiring views.
4.98 out of 5 average rating, 565 reviews
Ashland Zen Den
Brand new remodeled and designed downstairs basement apartment on Main St. in Ashland. This space is modern, 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!
4.94 out of 5 average rating, 144 reviews
Tiny Groove with plunge pool and soaking tubs
A unique off grid experience awaits you at our eco-friendly solar powered tiny home on 6 secluded acres. The home site is perfectly cut into a groove in the hillside 200 feet above the valley below allowing for beautiful Mountain views and amazing privacy with no visible neighbors other than the variety of local wildlife. Enjoy the outdoor soaking tubs, wood fired sauna and a seasonal plunge pool. Just a short 5 minute drive to the lovely town of Rogue River and access to I-5. Pet friendly too!
4.86 out of 5 average rating, 132 reviews
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.
4.97 out of 5 average rating, 516 reviews
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.
4.97 out of 5 average rating, 321 reviews
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.
4.83 out of 5 average rating, 286 reviews
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!
4.93 out of 5 average rating, 212 reviews
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!
4.95 out of 5 average rating, 168 reviews
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.
4.99 out of 5 average rating, 194 reviews
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.
5.0 out of 5 average rating, 304 reviews
Mindy’s Ashland Hideaway
Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!
4.9 out of 5 average rating, 201 reviews
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.
4.97 out of 5 average rating, 324 reviewsPopular amenities for holiday rentals near Mt. Ashland Ski Area
Apartment rentals with wifi

The Executive Suite
4.91 out of 5 average rating, 209 reviews
Plaza North Suite 201 Alexander
5.0 out of 5 average rating, 78 reviews
Creekside Studio • Walk to Downtown & Britt
4.99 out of 5 average rating, 83 reviews
Spacious Modern Condo Walk To Downtown & OSF
4.92 out of 5 average rating, 64 reviews
Plaza North Penthouse
5.0 out of 5 average rating, 35 reviews
Plaza North Suite 203 Windsor
4.97 out of 5 average rating, 66 reviews
Plaza North Suite 202 Sonoma
4.94 out of 5 average rating, 48 reviews
Black Pearl
4.89 out of 5 average rating, 98 reviewsFamily-friendly house rentals

Beautiful Country Home next to Jacksonville!
4.96 out of 5 average rating, 155 reviews
Charming house two blocks from downtown Ashland
4.88 out of 5 average rating, 182 reviews
Phoenix Rising
4.96 out of 5 average rating, 183 reviews
Spa Like Stay at the Britt Bungalow in J’Ville
4.99 out of 5 average rating, 348 reviews
Designer Home w/ Chef’s Kitchen
4.99 out of 5 average rating, 162 reviews
Rogue Reefs
4.98 out of 5 average rating, 126 reviews
Beautiful and peaceful cottage close to downtown
4.9 out of 5 average rating, 173 reviews
Historic 1875 Kitchen House
4.99 out of 5 average rating, 127 reviewsApartment rentals with air conditioning

Clean, Stylish Apt w/kitchen. block from Downtown
4.89 out of 5 average rating, 890 reviews
The Carriage House, Winner 2025 Best of Ashland!
4.89 out of 5 average rating, 300 reviews
Affordable Luxury- One block to Downtown
4.94 out of 5 average rating, 233 reviews
Downtown 3 Bedroom Upstairs Flat with views "B"
4.91 out of 5 average rating, 100 reviews
Designer 1 BD Apt | W/ W&D | Near I-5 & DT
4.82 out of 5 average rating, 556 reviews
Suite Comice EV Charging
4.96 out of 5 average rating, 502 reviews
Madrona Suite
4.99 out of 5 average rating, 273 reviews
5 Star Luxury Southern Oregon Suite
4.95 out of 5 average rating, 219 reviewsOther great holiday rentals near Mt. Ashland Ski Area

Charming very well appointed cottage !
4.95 out of 5 average rating, 500 reviews
Vineyard Cottage-Winery, Hot Tub, Privacy
4.93 out of 5 average rating, 269 reviews
The Greenwood Villa w/wood fire hot tub
4.93 out of 5 average rating, 466 reviews
Chalet in the Woods
4.97 out of 5 average rating, 248 reviews
Bluemoon Vacation Rentals - Cabin 52
4.85 out of 5 average rating, 123 reviews
Historic carriage house close to downtown Ashland
4.98 out of 5 average rating, 130 reviews
Penthouse Suite, easy walk to downtown.
4.99 out of 5 average rating, 143 reviews
Kelly’s Carriage House 4 miles from Ashland
4.97 out of 5 average rating, 397 reviews




