Cottage vacation rentals in Jackson County

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Top-rated cottage rentals in Jackson County

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Guest favorite

An inviting living area features a leather couch, a patterned chair, and a wooden coffee table on a soft area rug. A floor lamp stands beside the couch, offering ambient light, while framed artwork and wooden accents enhance the rustic charm.

Cottage in Ashland

4.95 out of 5 average rating, 420 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.

Guest favorite

A wooden table is set outdoors, displaying a charcuterie board with meats, cheese, olives, and bread. Two glasses of rose wine sit beside the board, with a bottle in the background. Sunlight illuminates the distant hills and green landscape, creating a serene outdoor dining scene.

Cottage in Grants Pass

4.96 out of 5 average rating, 245 reviews

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.

Guest favorite

Cottage in Days Creek

4.94 out of 5 average rating, 124 reviews

The Rustic Shanty-Farm Breakfast Included

Nestled in the Umpqua Forest, The Rustic Shanty is a fully remodeled cottage within walking distance to the South Umpqua River. It is a great launching point for daily adventures such as Crater Lake and Wild Life Safari, or sit back and relax while taking in the mountain views. This house features two bedrooms, two bathrooms, and a fully stocked kitchen. We also include our famous, you-cook breakfast with sausage and eggs produced at our nearby farm! We are dog friendly but Do Not allow CATS

Top guest favorite

An arched trellis covered with lush greenery leads through a garden path. Flanked by flowering plants and decorative fencing, a blue chair is positioned at the end of the path, which is lined with gravel, creating a serene outdoor space.

Cottage in Central Point

4.98 out of 5 average rating, 453 reviews

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

Top guest favorite

A modern cottage features a sleek exterior with large glass doors and contemporary lighting. The front porch is adorned with decorative plants and a small seating area. Natural wood accents and a gravel pathway enhance the welcoming ambiance of the outdoor space.

Cottage in Phoenix

4.99 out of 5 average rating, 428 reviews

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.

Guest favorite

A covered outdoor seating area features comfortable white sofas and a wooden coffee table. A view of the lawn, dotted with greenery and a small outbuilding, is visible in the background. The scene is framed by light-colored beams and soft natural lighting.

Cottage in Central Point

4.96 out of 5 average rating, 112 reviews

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.

Top guest favorite

A scenic view showcases the deep blue waters of Crater Lake, framed by lush evergreen trees. The surrounding cliffs and hills are visible in the background under a clear blue sky, creating a tranquil and natural setting.

Cottage in Shady Cove

4.99 out of 5 average rating, 114 reviews

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.

Top guest favorite

The outdoor patio features comfortable seating and a table set beneath a shaded umbrella. Lush greenery and decorative plants surround the hot tub, creating a tranquil space for relaxation. A wooden fence and well-maintained landscaping enhance the privacy of this inviting area.

Cottage in Ashland

4.93 out of 5 average rating, 232 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.

Guest favorite

A spacious back deck features wooden flooring and a decorative lattice screen for privacy. Two chairs are positioned around a table with an umbrella providing shade, creating an inviting space for relaxation and outdoor dining.

Cottage in Medford

4.94 out of 5 average rating, 438 reviews

Efficient, clean, pet-friendly 2 bed/bath cottage

Our 2 bedroom 2 bath guesthouse is a gem! Located in a quiet neighborhood in SE Medford with a garden and spacious back deck you'll be just a few minutes from downtown, both local hospitals, and the airport with easy access to the freeway. This home is just 20 minutes from downtown Ashland and Jacksonville. A great spot for families. Well-behaved pets welcome! *We sanitize commonly touched surfaces after each booking and comply with Airbnb's enhanced cleaning procedures*

Guest favorite

Cottage in Jacksonville

4.91 out of 5 average rating, 201 reviews

Cottage on River Farm -Applegate Wine Trail

Classical cottage on a 5-acre micro-farm, on the Applegate River near vineyards. This cozy cottage on "Red Barn Farm" is a mini farm-stay experience with goats & chickens along the Applegate Valley Wine Trail. Walk to Red Lily Vineyards! Enjoy the private firepit 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.

Superhost

A welcoming entrance is highlighted by a colorful flower garden, featuring an array of blooms in pink, red, and white. The cottage sign, framed by white lattice, is prominently displayed above the path leading to the covered porch, which is adorned with red accents.

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!

Superhost

Several wooden picnic tables are placed on a grassy area beside the tranquil Rogue River, surrounded by trees and greenery. A barbecue pit is visible nearby, complementing the serene outdoor setting.

Cottage in Gold Hill

4.78 out of 5 average rating, 409 reviews

Rogue Rivers Edge | 1 BR Fishing Inspired Cottage

Fishing-Themed Cottage - Perfect Road Trip Stop Along I-5 - Private Hot Tub - Situated right on the edge of the beautiful Rogue River - Has short path leading down to the river's edge - Glamping Vibes - Tempurpedic Queen mattress - With Smart TV - All the essentials for a comfy stay (linens, towels, etc.) - Perfect for a peaceful getaway or a fishing trip!