Cottage vacation rentals in Jackson County

A cozy living area features a leather sofa and a patterned armchair, complemented by a wooden coffee table. A flat-screen TV is mounted on the wall, while large windows allow natural light to fill the space, highlighting the warm wood paneling.

4.95 out of 5 average rating, 438 reviews

Charming very well appointed cottage !

The Farm 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 2 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 quiet is what you are looking for, the cottage will meet all your needs.

4.96 out of 5 average rating, 260 reviews

A welcoming cottage exterior is framed by greenery, featuring a charming front porch with seating and flower pots. A gravel pathway leads to the entrance, which has a bright front door and decorative elements enhancing the inviting entrance.

Cottage in Grants Pass

Applegate cottage at boutique winery!

Located right in the middle of Southern Oregon wine country. You will be staying in a cottage on a vineyard with our own winery and tasting room onsite. Tasting room open Saturday & Sunday. (April-December) With 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport, Troon, Schultz, Schmidt, Blossom Barn, Rosellas & Solaro just to name a few. Downtown Grants Pass & Jacksonville are 30 minutes away. Highway 5 is 30 min away.

The inviting living area showcases a stone fireplace as a focal point, complemented by a wooden mantel. Sunlight filters through large windows, illuminating a seating area with a comfortable chaise lounge and a wooden table. A rich area rug adds warmth to the hardwood floor.

4.97 out of 5 average rating, 478 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.

4.98 out of 5 average rating, 482 reviews

An exterior view of the Garden Cottage is presented, featuring a welcoming blue façade. The entrance is highlighted by a white door adorned with a seasonal wreath. Windows flank the door, each with planters beneath, and decorative lights embellish the roofline.

Cottage in Central Point

Country Garden Cottage

Newly remodeled Garden Cottage with living area/kitchenette, bedroom, and bathroom. Cottage has high ceilings, ceramic tile floors, quartz countertop, cherry wood cabinets and new mini-split heater/air conditioner. It is bordered on two sides by a garden common area with seating, fountain, and a grape vine covered pergola. New Roku TV installed. Conveniently located: * 5 min to I-5 * 10 min to airport * 3 min to Central Point * 10 min to Medford * 5 min to Jacksonville * 25 min to Ashland

4.99 out of 5 average rating, 448 reviews

An open living space features a comfortable gray sofa adorned with two yellow cushions. A wooden coffee table rests on a colorful area rug, and the kitchen area showcases white cabinetry. Bright light enters through windows and a glass door, leading to a private outdoor area.

Cottage in Phoenix

Modern Getaway on Sunflower Farm

Stunning modern getaway on a flower farm with spectacular views. Nestled in the heart of the valley. 15 minutes from Ashland and Jacksonville. Home of Shakespeare and Britt Festivals. Over 6 wineries and a distillery within a 3 mile radius. Bright design with beautiful features. The many windows and French doors offer light in all directions with views of sunflowers, pear orchards and Roxy Ann Peak. One mile from the Greenway, a bike and pedestrian pathway linking Central Point to Ashland.

4.97 out of 5 average rating, 122 reviews

A bright kitchen features large windows allowing natural light to illuminate white cabinetry and countertops. An island with barstools offers additional seating, while a chandelier hangs above, providing a warm focal point. Stylish accents, including potted plants and a decorative tray, enhance the inviting space.

Cottage in Central Point

Sweet Rose Cottage

This beautifully designed 1800 sq/ft cottage at Sweet Rose Farm offers rare seclusion and privacy located very close to historic Jacksonville. Bountiful views of agricultural land surrounds with pear orchards, fields, vineyards, ponds and of course the beautiful horses stabled at Sweet Rose Farm. The furnishings, beds and bedding are as expected at higher price points. Relax inside or out with a cup of coffee from the Jura espresso machine while taking in the many views from every window.

4.92 out of 5 average rating, 212 reviews

The classic cottage is framed by green foliage, showcasing a welcoming entryway with a black door and a symmetrical window. A bench is positioned on the porch, complemented by flower pots on either side. The gravel path leads to the entrance, surrounded by trees.

Cottage in Jacksonville

Cottage on River Farm -Applegate Wine Trail

Classic one-room cottage on a 5-acre micro-farm, on the Applegate River near vineyards. This cozy cottage is a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit (when not in wildfire season) with complimentary s’mores kit or walk down to the river and breath. We are 15 minutes from the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival. Wine Country Farm Stay dot come.

4.99 out of 5 average rating, 122 reviews

The tranquil Upper Rogue River is captured, reflecting a vibrant blue sky. Lush green trees line the riverbank, with a distant view of a cottage nestled among the foliage, creating a serene and natural setting.

Cottage in Shady Cove

Rogue River Retreat

Located on the Upper Rogue River, this riverfront cottage is perfect whether you seek a quiet weekend away or fishing for steelhead, (plus, there's a great run right in front of the cottage). We're just down the way from the Riverhouse and bridge, close to town. It is a very quiet and serene atmosphere, perfect for unwinding. The geese will wake you up in the morning and the deer and raccoons will amuse you. Feel free to pick fruit from the trees if in season. Sorry, no children.

A vibrant metal dragon sculpture stands prominently in a landscaped garden, featuring red and metallic hues. Surrounding decorative stones add texture, while various plants create a colorful backdrop against a clear blue sky.

4.99 out of 5 average rating, 201 reviews

The Red Dragon House

Just a few minutes outside of Ashland, this unique and spacious property will put you in a rural setting with excellent views of the surrounding hills of the Rogue Valley. Located on 5.2 acres, with two security gates that are, remnants of a previous cannabis operation, the property affords ample privacy, and is invisible from the street, providing a perfect getaway for those that seek it. We are adjacent to I-5, so if road noise is an issue, this property may not be right for you.

A light-filled living room features large windows and a skylight, enhancing the warm tones of the wood flooring. A cozy seating area includes a leather sofa and an armchair, accompanied by a small coffee table. A stylish wood stove adds a functional and aesthetic touch.

4.93 out of 5 average rating, 240 reviews

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.