Holiday rentals in Ashland

Refined, Serene Home in Jacksonville

Professionally decorated in a Mid-Century Modern style. Sleep soundly on Hungarian down pillows and BeautyRest Black mattresses made up with soft 600 thread-count Italian linens. Beautifully tiled bathroom offering Turkish towels, bathrobes, and luxe sundries. Living room and full kitchen with gas stove and quartz counter tops. Step outside to a private yard with outdoor eating area and cozy fire pit. Other amenities include three flat-screen Smart TV's, cable, WIFI, washer and dryer and so much more. Come and enjoy! You'll have this complete private cottage to yourself with private (and ample) parking. Come and go as you please in complete privacy. Self Check-in Available I'm available, if needed. I typically give a complete walk through of the property. For busy travelers, special arrangements can be made to stock the kitchen with additional supplies such as eggs, juice, special drinks. Our goal is to provide you with wonderful service. Let us know how we may help you have a terrific stay. The house is set in a laid-back neighborhood with a mix of shopping and dining within walking distance to Jacksonville's historic core. Ashland and Oregon Shakespeare Festival are a 15 minute drive away. 9% City Guest Tax will be applied to nightly rate & any additional charges. Tax is billed at arrival and must be paid via cash or check before departure. Airbnb is not allowed to collect this tax in advance.

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!

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.

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!

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil tiny studio cottage. Perfectly located minutes off I-5 and just 3 miles from downtown Ashland—home to the Oregon Shakespeare Festival, Plaza shops, Lithia Park and restaurants. Explore Crater Lake, historic Jacksonville, and wineries in the picturesque Rogue Valley. Enjoy the privacy of our gated property with peaceful farm surroundings! Pets accepted with pet fee. No cleaning fee's for stays! Large parking lot for trailers and moving trucks.

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

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.

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.

Kelly’s Farm 4 miles to Ashland

Nestled on the border of the Shakespeare hamlet of Ashland, Oregon, is Kelly’s farm. Only four miles away from Ashland. Kelly’s farm has horses, goats, chickens, gardens, fruit and nut trees with views of Mt. Ashland’s seven-thousand feet high profile in its front and bucolic rolling hills in its back. Bring your dog! You have access to a large fenced in yard right from your private entrance and deck. ***Unfortunately we are not set up for children under 4 or kitty cats.

The Epic A - Charming 1960s A-Frame w/Hot tub

Introducing The Epic A, an A-frame style home in the Southern Oregon countryside minutes from downtown. This charming space is perched on a hillside with a view of the local mountains, a hot tub, and everything you need to enjoy your visit to Grants Pass. The hosts have taken special care to balance vintage style with modern comforts and create a relaxing atmosphere. Expect quiet evenings and wildlife visits on this beautiful acre property.

Starlight Cottage at Chozu Gardens

This charming cottage is located in the historic railroad district home to coffee houses, restaurants, and galleries. A 5 minute walk to downtown. It has a full kitchenette, fireplace like heater, orthopedic bed/ pillows and relaxing décor. Private garden patio. Located one door down from Chozu Gardens (closed Mondays guests can take advantage of a 20% discount to soak and sauna in this serene setting.)

Artsy MCM Guesthouse w/ Spa Soaking Tub

2-Bedroom Guest Home - Perfect Stop-Over on Your Oregon Road Trip - Hot Tub - 2 Queen beds - Luxurious soaking tub - Gas fireplace - Walking distance to The Phoodery! - Private & Secluded - Tucked behind the front house for privacy - 1 mile from I-5 access - 7 miles to Ashland - 7 miles to Medford - Come explore the charming small town of Phoenix, Oregon - Nearby wine country for tasting and exploration