Cottage holiday rentals in Ashland

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Top-rated cottage rentals in Ashland

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Guest favourite

Cottage in Grants Pass

4.96 out of 5 average rating, 225 reviews

Applegate Wine Country cottage!

Our "Lil Wanderer" cottage is 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. We’re open Saturday & Sunday. Also, with 7 wineries under 5 minutes away from the cottage, you’ll have plenty to explore right out your front door. Wooldridge, Walport,Troon, 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 favourite

Cottage in Ashland

4.96 out of 5 average rating, 402 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 favourite

Cottage in Ashland

4.97 out of 5 average rating, 446 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.

Guest favourite

Cottage in Central Point

4.98 out of 5 average rating, 432 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

Guest favourite

Cottage in Central Point

4.96 out of 5 average rating, 107 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.

Guest favourite

Cottage in Shady Cove

4.99 out of 5 average rating, 113 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.

Guest favourite

Cottage in Ashland

4.99 out of 5 average rating, 169 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 favourite

Cottage in Ashland

4.92 out of 5 average rating, 222 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.

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Cottage in Gold Hill

4.84 out of 5 average rating, 188 reviews

Hot Tub w/ River Views / Private Patio / Spacious

This stylish 2 bedroom apartment is a perfect stop over off of I-5 for a traveling family or friends. Enjoy the river views from private hot tub on the patio. The tranquil location on the river also makes for a unique destination if you choose to stay a few nights! It's located just down the road from Del Rio Vineyards and equal distance to quaint small towns Gold Hill and Rogue River Oregon. There's plenty to explore should you choose to settle in and stay awhile!

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Cottage in Grants Pass

4.85 out of 5 average rating, 281 reviews

Riverfront House with hot tub, game room and more!

Welcome to your escape on the Rogue River. This is our adorable home on the river front, with tons of things to do. 2 decks, hot tub, river front swing, full game room, and sleeping for 14. This house in on a quiet street, and just 5 minutes off the freeway. If you’re looking to relax with the family, or explore everything Southern Oregon has to offer, this is the Airbnb for you! Make some memories at this unique and family-friendly place.

Guest favourite

Cottage in Talent

4.76 out of 5 average rating, 421 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.

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Cottage in Ashland

4.79 out of 5 average rating, 308 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.

Holiday rentals for every style

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Popular amenities for cottage rentals in Ashland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Talent

4.94 out of 5 average rating, 16 reviews

Paschal Winery - Dream 1 Cottage

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Cottage in Talent

4.75 out of 5 average rating, 16 reviews

Paschal Winery - Dream 2 Cottage

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Cottage in Talent

Paschal Winery Paschal Compound

Cottage in Gold Hill

4.73 out of 5 average rating, 343 reviews

R&R Overlooking the Rogue | 2 bed | Hot Tub.

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Pet-friendly cottage rentals

Guest favourite

Cottage in Central Point

4.91 out of 5 average rating, 65 reviews

Charm Cottage close to wineries & shopping

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Cottage in Ashland

4.71 out of 5 average rating, 34 reviews

ArtyCottage built by a custom furniture maker.

Cottage in Central Point

5 out of 5 average rating, 4 reviews

Cheerful cottage in Southern Oregon

Guest favourite

Cottage in Ashland

4.95 out of 5 average rating, 39 reviews

Sweet Breeze Bungalow

Guest favourite

Cottage in Jacksonville

4.91 out of 5 average rating, 192 reviews

Cottage on River Farm -Applegate Wine Trail

Cottage in Ashland

4.94 out of 5 average rating, 18 reviews

4 miles 2 OSF Cottage

Guest favourite

Cottage in Shady Cove

4.85 out of 5 average rating, 53 reviews

Eagles Nest on the Rogue River

Guest favourite

Cottage in Jacksonville

4.9 out of 5 average rating, 29 reviews

RIDER HOUSE Historic Cottage Modernized Interior

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Private cottage rentals

Cottage in Ashland

4.98 out of 5 average rating, 43 reviews

Garden Cottage sleeps five w/2 full baths downtown

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Cottage in Central Point

4.78 out of 5 average rating, 23 reviews

Beautiful cottage w/pool in bamboo forest

Guest favourite

Cottage in Jacksonville

4.88 out of 5 average rating, 72 reviews

Historic Bradshaw House!

Guest favourite

Cottage in Phoenix

4.99 out of 5 average rating, 413 reviews

Modern Getaway on Sunflower Farm

Guest favourite

Cottage in Grants Pass

5 out of 5 average rating, 63 reviews

The Cherry Cottage with built in pool

Guest favourite

Cottage in Hornbrook

4.98 out of 5 average rating, 48 reviews

"Casa del Sol" Delightful cottage on CA/OR Border

Guest favourite

Cottage in Grants Pass

4.93 out of 5 average rating, 59 reviews

Private/Spacious/LazyBoy/Fully Stocked/300mbps

Guest favourite

Cottage in Jacksonville

5 out of 5 average rating, 33 reviews

Cottage A is a great getaway

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Quick stats about cottage rentals in Ashland

Total rentals
20 properties
Nightly prices starting at
£38 before taxes and fees
Total number of reviews
2.1K reviews
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Lithia Park, Oregon Shakespeare Festival and Ashland Food Co-op

Cottage holiday rentals in Ashland

Top-rated cottage rentals in Ashland

Holiday rentals for every style

Cabins

Houses

Flats

Popular amenities for cottage rentals in Ashland

Cottage rentals with a hot tub

Cottage in Talent

Cottage in Talent

Cottage in Talent

Cottage in Gold Hill

Pet-friendly cottage rentals

Cottage in Central Point

Cottage in Ashland

Cottage in Central Point

Cottage in Ashland

Cottage in Jacksonville

Cottage in Ashland

Cottage in Shady Cove

Cottage in Jacksonville

Private cottage rentals

Cottage in Ashland

Cottage in Central Point

Cottage in Jacksonville

Cottage in Phoenix

Cottage in Grants Pass

Cottage in Hornbrook

Cottage in Grants Pass

Cottage in Jacksonville

Quick stats about cottage rentals in Ashland

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

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