Cottage vacation rentals in Jackson County

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Top-rated cottage rentals in Jackson County

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Guest favorite

Cottage in Grants Pass

4.96 out of 5 average rating, 248 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.

Top guest favorite

Cottage in Ashland

4.97 out of 5 average rating, 466 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, 456 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

Cottage in Phoenix

4.99 out of 5 average rating, 432 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

Cottage in Central Point

4.96 out of 5 average rating, 113 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

Cottage in Ashland

4.99 out of 5 average rating, 181 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 private deck area features a hot tub surrounded by natural landscaping and a gentle lawn that slopes towards the vineyard. A small wooden bench is positioned nearby, while trees provide shade against the clear blue sky.

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, 441 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, 203 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, 413 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.

Superhost

Cottage in Gold Hill

4.85 out of 5 average rating, 228 reviews

Hot Tub w/ River Views / Private Patio / Spacious

Charming 2-Bedroom Apartment with River Views - Perfect stopover for traveling families or friends - Has a private Hot Tub - Nestled along the river - Just down the road from Del Rio Vineyards. Equal distance to the charming small towns of Gold Hill and Rogue River, Oregon. - Perfect base for exploring local sights or enjoying the serene surroundings for a few nights.