Holiday rentals with a fireplace in Jackson County

4.98 out of 5 average rating, 492 reviews

Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

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Home in Medford

4.91 out of 5 average rating, 107 reviews

Hillcrest Estates

Gorgeous custom built home on a Private Road in very desirable East Medford Hills - Open Floor Plan - Living room & master bedroom opens to a covered deck. Crown molding, beautiful kitchen w/slab granite counters & Stainless Steel appliances, gas fireplace w/slate surround & mantel, hardwood flooring, natural Beech wood cabinetry, 12' ceilings +more. The master suite features a soaking tub, glass-surround shower, double vanity. Lower level has 2 bedrooms, a full bath & exit to covered patio.

Guest suite in Jacksonville

4.88 out of 5 average rating, 103 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.

4.99 out of 5 average rating, 152 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. Charging is available for your electric cars in the upper parking area.

4.96 out of 5 average rating, 108 reviews

Home in Prospect

Ripple Rock Ranch Lodge

The Ripple Rock Lodge offers amazing views of The Rogue River Gorge and Lost Creek Lake. The lodge has a large patio with ambient lighting, and both gas and charcoal grills! It is located on a 10 acres parcel of woodlands to explore with access to the Rogue River and numerous hiking trails. Medford International Airport is approximately 40 miles from the Lodge and Crater Lake National Park is approximately 35 miles. Now offering as a wedding venue, please message with any inquiries!

5 out of 5 average rating, 123 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.

4.93 out of 5 average rating, 232 reviews

Cottage in Ashland

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.

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Cottage in Ashland

4.84 out of 5 average rating, 103 reviews

Oak Hideaway Cottage

Oak Hideaway's charm abounds, from the built-in seating on your porch, to the fireplace in the living room, to the faux finished walls throughout. This cottage also offers the convenience of handicap accessibility, handy for those young ones in strollers, as well. With a mirror floor plan to Oak Lawn's, across the way, 3 queen beds sleep 6 comfortably. Walk out your private entrance just a short block to downtown where theaters, restaurants and art galleries await you!

4.92 out of 5 average rating, 176 reviews

Flat in Medford

Broken Chair Ranch

Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit on the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

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Home in Gold Hill

4.87 out of 5 average rating, 162 reviews

Drift Away

Drift Away, your dreamy paradise on the Rogue River with private river access at the center of Southern Oregon's attractions. The house sleeps 14 people. Fireside and River View dining make this a special place for families or simply to get away from the crowds to escape to your private boating and fishing oasis. Near the airport, shopping, golf, rafting, fishing, hiking, biking, wine tours, jet boats.

4.9 out of 5 average rating, 204 reviews

Home in Medford

Hot Tub huge yard 5 kings fiber wi-fi 4k huge tv

Brand new home with stunning hill views on a corner lot. Huge backyard with hot tub, kidss’ toys, and playground. Fast fiber internet—great for remote work. Quartz counters, stylish finishes, and new appliances. No significant outdoor noise after 10 PM—strict rule. $30/night per dog, with approval. Close to shopping. Great for families, groups, and relaxing getaways!