Cottage vacation rentals in Jackson County

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Top-rated cottage rentals in Jackson County

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Guest favorite

Vibrant gardens are highlighted by greenery and colorful flowers, including purple blooms and a variety of seasonal plants. A white picket fence frames the lush yard, creating a tranquil outdoor space surrounded by trees and blue skies.

Cottage in Grants Pass

4.96 out of 5 average rating, 250 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, 126 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

A combined laundry unit is visible, with a washing machine and dryer stacked. The adjacent bathroom area features a white sink with a wall-mounted mirror, a toilet, and a wooden chair positioned nearby. Soft lighting enhances the workspace.

Cottage in Ashland

4.97 out of 5 average rating, 469 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.

Top guest favorite

A garden common area is bordered by lush greenery and flowering plants. A stone pathway leads through the vibrant landscape, while a pergola covered in grape vines provides shaded seating. Decorative elements like a fountain and various garden plants enhance the serene environment.

Cottage in Central Point

4.98 out of 5 average rating, 460 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 golden retriever sits calmly in a grassy area, adorned with a colorful bandana. A white fence borders the space, while a garden with flowers is visible in the foreground. In the background, a mountain range under a partly cloudy sky is seen.

Cottage in Phoenix

4.99 out of 5 average rating, 436 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 decorative black metal gate features a 'Welcome' sign with a horse silhouette, inviting guests into the garden area. The background reveals a light-colored building with multiple windows, surrounded by a well-maintained landscape of natural wood mulch and greenery.

Cottage in Central Point

4.97 out of 5 average rating, 115 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, 115 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

Cottage in Ashland

4.99 out of 5 average rating, 186 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.

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, 450 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

A child stands in a lush green pasture, facing a friendly goat. The child holds a leafy snack, while sunlight filters through the surrounding trees. The vibrant greenery of the grass and clover creates a natural backdrop, enhancing the interaction between the child and the goat.

Cottage in Jacksonville

4.91 out of 5 average rating, 206 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.

Guest favorite

A well-structured wooden enclosure houses a spacious hot tub, surrounded by lush planters. Steps lead up to the tub, which is illuminated by soft overhead lighting that highlights the inviting water. The walls feature natural wood slats, enhancing the warm ambiance.

Cottage in Jacksonville

4.94 out of 5 average rating, 416 reviews

Romantic Retreat w/ Hot Tub & Starlit Massage Room

The Applegate Spa is a top-rated romantic retreat in Southern Oregon’s stunning Applegate Valley. Perfect for couples, it features a private hot tub, cozy fireplace, and a dreamy massage room beneath a glowing starlight ceiling. Surrounded by vineyards, rivers, and charming wineries, this peaceful escape blends rustic charm with comfort and relaxation. Just minutes from historic Jacksonville and scenic trails, it’s the ideal place to unwind, explore, and reconnect.

Guest favorite

A framed instructional sign details how to adjust water temperature with a small lever, clearly indicating red for hot and blue for cold. An illustrated faucet shows a red arrow pointing to a knob with a note indicating to pull down on it to use the shower.

Cottage in Talent

4.77 out of 5 average rating, 439 reviews

" sweet little garden studio "

Nice little shady deck with rocking chairs. Very quiet and safe little neighborhood. Great location. Eight minutes to downtown Ashland and 15 minutes to downtown Medford. Comfortable little Studio. Great for one or two busy guest. If bringing an animal please lmk beforehand of what kind and size. Im allowing one well behaved animal. Must not be left behind and clean up is a must. Thank you for understanding.