Cottage holiday rentals in Ashland

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, 510 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.

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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.

4.98 out of 5 average rating, 535 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

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4.99 out of 5 average rating, 486 reviews

Cottage in Phoenix

Wine Country Farm Stay Near Ashland

Stunning romantic wine getaway on a flower farm with spectacular views. Farm stay offers the perfect base for exploring the Rogue Valley wine trail, 15 minutes to over 20 Jacksonville and Ashland wineries in the heart of the valley. Cozy private deck offers a perfect spot to relax and enjoy wine with views of mountains, pastures, and fields. Home of the Oregon Shakespeare and Britt Festivals. One mile from the Greenway, a bike and pedestrian pathway. Enjoy a beautiful ride to local wineries.

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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.

4.94 out of 5 average rating, 489 reviews

Charming very well appointed cottage !

The 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 1 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 comfort what you are looking for, the cottage will meet all your needs.

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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.

4.93 out of 5 average rating, 240 reviews

Cottage on River Farm -Applegate Wine Trail

Cozy one-room cottage on a 5-acre micro-farm, on the Applegate River near vineyards. Set halfway between Crater Lake & the Redwood Forest, the Applegate Valley is a lush valley with 19 artisan vineyards. This classic cottage is a mini farm-stay experience with goats & chickens. Walk to Red Lily Vineyard! Enjoy the private firepit with complimentary s’mores kit or walk down to the river to swim. Nearby: the historic gold-rush town of Jacksonville, home of the Britt Summer Music Festival.

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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.

4.96 out of 5 average rating, 289 reviews

Applegate cottage at boutique winery!

Located right in the middle of Southern Oregon Applegate 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. 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

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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.

4.92 out of 5 average rating, 263 reviews

Vineyard Cottage-Winery, Hot Tub, Privacy

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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4.92 out of 5 average rating, 523 reviews

A modern living area is highlighted by a gray upholstered sofa and matching ottoman. A wooden coffee table with a decorative centerpiece sits in front of the sofa. A well-equipped kitchen with bar seating is visible in the background, complemented by warm wood tones and natural light.

Cottage in Medford

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*

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An outdoor hot tub is illuminated under warm string lights, set within a wooden gazebo. The surrounding area features wooden fencing and lush greenery, creating a serene environment. A soft blue glow from the water contrasts with the warm evening sky, enhancing the tranquil ambiance.

4.93 out of 5 average rating, 479 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.

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A cozy living area features a blue sectional sofa and an accent chair, with a flat-screen television mounted on the wall. A sliding barn door leads to the kitchen area, which showcases modern appliances. Natural light filters through the window, enhancing the spaciousness.

4.98 out of 5 average rating, 139 reviews

Sweet Breeze Bungalow

Charming Alley bungalow in the historic railroad district. Walk score of 93. Immerse yourself in the heart of Ashland. 5 min. walk to downtown, an easy 8 min. walk to Shakespeare & Cabaret Theaters. Walk to pubs, restaurants, coffee shops, spa's, markets, movie theater, Lithia Park, Japanese garden and trailheads all within 5-12 mins. Nice bike ride to wineries 15 min away, or a 30 min. drive to Mt. Ashland for skiing, hiking, biking and more adventures.

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4.78 out of 5 average rating, 468 reviews

A rocking chair is positioned on a shaded deck, framed by vibrant purple flowers. The chair features a decorative cushion, while green foliage surrounds the scene, creating a serene outdoor space that invites relaxation.

Cottage in Talent

" 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.

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The interior space features a wooden dining table set with two wine glasses, surrounded by four black stools. A partially open door reveals a separate bedroom with a spacious bed, and light fixtures add soft lighting throughout the area.

4.79 out of 5 average rating, 363 reviews

Oak Street Studio

Originally built as a retail space for the Oak Street Cottages, the Oak Street Studio is actually facing Water Street with large windows bringing in loads of natural light. Just a few blocks to Lithia Park, Allen Elizabethan Theatre, Angus Bowmer Theatre, and Thomas Theatre. Also nearby are Oregon Cabaret Theatre and Ashland Library. Part of Oak Street Cottages.

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Popular amenities for Ashland cottage rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.82 out of 5 average rating, 315 reviews

Cottage in Gold Hill

Hot Tub w/ River Views / Private Patio / Spacious

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4.93 out of 5 average rating, 71 reviews

A comfortable living area features a large sectional sofa and a cozy armchair, complemented by a decorative coffee table. A flat-screen TV is mounted on the wall, alongside a beautiful electric fireplace. Natural light floods in through large windows framed by dark curtains, revealing scenic views.

Cottage in Talent

Paschal Winery - Dream 1 Cottage

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A wooden deck overlooks the Rogue River, surrounded by trees displaying autumn colors. Two chairs are positioned on the deck, offering a serene view of the water and lush landscape. Steps lead down from the deck to a landscaped area with gravel and plants.

4.8 out of 5 average rating, 363 reviews

Riverfront House with hot tub, game room and more!

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4.91 out of 5 average rating, 54 reviews

An outdoor patio is highlighted by a private hot tub and comfortable seating arrangement, surrounded by scenic views of hills and vineyards. A hammock is present nearby for relaxation, with a small table positioned for added convenience.

Cottage in Talent

Paschal Winery - Dream 2 Cottage

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Pet-friendly cottage rentals

A fenced front yard is displayed, featuring a porch with two blue chairs and a small table. String lights are hung above, adding a warm touch. The entrance to the cottage is framed by two black shutters, leading into a bright and welcoming space.

4.91 out of 5 average rating, 190 reviews

Farm Cottage 1/2 Mile Outside Jacksonville

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An outdoor seating area is presented with four cushioned chairs surrounding a central fire pit table. A patterned outdoor rug adds color beneath the seating, while a scenic view of rolling fields and trees is visible in the background.

4.91 out of 5 average rating, 105 reviews

Cozy 2BR Cottage | Quiet, Private & Pet-Friendly

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A modern kitchen features stylish cabinetry and stainless steel appliances. The kitchen island, equipped with seating, invites gathering. Natural light enters through a window above the sink, complementing the high ceilings and exposed beams.

4.95 out of 5 average rating, 21 reviews

Cozy Modern Cottage

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A charming cottage is viewed from the street, surrounded by colorful landscaping. Soft light glows from the windows, while a white picket fence gives a welcoming impression. Nearby trees and shrubs add to the serene evening atmosphere, providing a sense of tranquility.

4.67 out of 5 average rating, 39 reviews

Bluemoon Vacation Rentals - Bluemoon Cottage

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A charming white cottage is surrounded by vibrant gardens, featuring colorful flowers and lush greenery. The welcoming front porch is adorned with seating, while a neatly manicured lawn extends beside a stone border.

4.93 out of 5 average rating, 56 reviews

Lily Pad/#1 Best Location/Full Kitchen/Luxurious

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4.73 out of 5 average rating, 15 reviews

Fireside Cottage

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InstaChill - Ashland Summer +WfH +4k Tv +WD +A/C

5.0 out of 5 average rating, 5 reviews

The welcoming exterior of the cottage is framed by lush green grass and a pathway leading to the entrance. Two comfortable chairs are positioned on the porch, inviting relaxation. Mature trees provide shade, enhancing the peaceful atmosphere of the outdoor space.

Cottage in Medford

Cottage-Near hospitals, fully fenced, pet friendly

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Private cottage rentals

Two wine glasses, each garnished with a strawberry, are placed on a wooden table. A bottle of white wine is positioned between the glasses. In the background, the lush greenery and the flowing Little Applegate River are visible, providing a tranquil setting.

5.0 out of 5 average rating, 15 reviews

Cottage on River's Edge

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The exterior of the cottage is highlighted by a vibrant blue façade and a white picket fence. Large windows allow ample natural light to enter, while a landscaped area with pebbles and a small tree enhances the inviting appearance of the home.

4.97 out of 5 average rating, 65 reviews

Mountain View Cottage

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A charming exterior view showcases the fully renovated single-level studio with a welcoming entrance. Lush greenery surrounds the structure, complementing the natural tones of the building. The spacious patio area features a few potted plants, and the driveway is accessible, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 34 reviews

The Monarch - Luxury Studio W/On-Site Parking

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A light gray sectional couch is adorned with decorative pillows in neutral tones. A wooden coffee table with a simple design sits in front, featuring a plant and a tray with items. A glimpse of the kitchen area is seen in the background.

4.98 out of 5 average rating, 50 reviews

Cottage A in Jacksonville is a great getaway

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The kitchen features wooden cabinetry and a vibrant backsplash, with stainless steel appliances including a gas stove and hood. Open shelving displays dishes and cooking essentials, while natural light enters through a nearby door. A wooden island is centered in the space, enhancing functionality.

4.92 out of 5 average rating, 36 reviews

Grants Pass Cottage for Long or Short stay

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A charming blue cottage is featured, adorned with climbing vines and surrounded by a well-maintained lawn. Colorful flowers are displayed in planters across the front. A welcoming front porch leads to the entrance, while tall trees frame the property against a clear blue sky.

4.6 out of 5 average rating, 10 reviews

Charming Cottage Close to Historic Grants Pass

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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.

4.97 out of 5 average rating, 139 reviews

Sweet Rose Cottage

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