Cottage holiday rentals in Ashland

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Top-rated cottage rentals in Ashland

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Guest favourite

Cottage in Ashland

4.96 out of 5 average rating, 368 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, 429 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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Cottage in Jacksonville

4.9 out of 5 average rating, 178 reviews

Farm Cottage on River - Applegate Wine Trail

Recently repainted and deep cleaned, cottage on a 5-acre, Applegate River farm near vineyards. This is a cozy cottage on "Red Barn Farm.” Enjoy 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 favourite

Cottage in Central Point

4.98 out of 5 average rating, 397 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 Ashland

4.99 out of 5 average rating, 145 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, 215 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 favourite

Cottage in Medford

4.94 out of 5 average rating, 415 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 favourite

Cottage in Grants Pass

4.96 out of 5 average rating, 199 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 on site opening in summer 2024! 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.

Guest favourite

Cottage in Gold Hill

4.87 out of 5 average rating, 165 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!

Guest favourite

Cottage in Talent

4.75 out of 5 average rating, 403 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

Superhost

Cottage in Ashland

4.78 out of 5 average rating, 292 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.

Guest favourite

Cottage in Central Point

4.9 out of 5 average rating, 144 reviews

Farm Cottage 1/2 Mile Outside Jacksonville

Private cottage with fenced yard. 1/2 mile to historic Jacksonville and the famous Britt Festival. Noted local winery Rellik is one property away and we are in the heart of the Rogue Valley wine country. Pool available in the summer and meeting our farm animals is available with advanced notice. Our place is designed to help you create lasting memories!

Holiday rentals for every style

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Popular amenities for Ashland cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Grants Pass

4.88 out of 5 average rating, 253 reviews

Riverfront House with hot tub, game room and more!

Guest favourite

Cottage in Talent

4.89 out of 5 average rating, 9 reviews

Paschal Winery - Dream 1 Cottage

Guest favourite

Place to stay in Jacksonville

5.0 out of 5 average rating, 102 reviews

Britt Cottage Perfect Location

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Cottage in Talent

Paschal Winery Paschal Compound

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Cottage in Talent

4.4 out of 5 average rating, 5 reviews

Paschal Winery - Dream 2 Cottage

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Pet-friendly cottage rentals

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Cottage in Ashland

4.64 out of 5 average rating, 11 reviews

Bluemoon Vacation Rentals - Bluemoon Cottage

Guest favourite

Cottage in Ashland

5.0 out of 5 average rating, 18 reviews

Sweet Breeze Bungalow

Guest favourite

Cottage in Central Point

4.9 out of 5 average rating, 59 reviews

Charm Cottage close to wineries & shopping

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Cottage in Ashland

4.7 out of 5 average rating, 33 reviews

ArtyCottage built by a custom furniture maker.

Guest favourite

Cottage in Grants Pass

5.0 out of 5 average rating, 49 reviews

The Cherry Cottage with built in pool

Guest favourite

Cottage in Jacksonville

4.96 out of 5 average rating, 23 reviews

RIDER HOUSE Historic Cottage Modernized Interior

Cottage in Gold Hill

4.78 out of 5 average rating, 377 reviews

Rogue Rivers Edge | 1 BR Fishing Inspired Cottage

Guest favourite

Cottage in Eagle Point

4.85 out of 5 average rating, 65 reviews

Blue Gate Cottage on the Rogue River

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Private cottage rentals

Guest favourite

Cottage in Shady Cove

5.0 out of 5 average rating, 98 reviews

Rogue River Retreat

Guest favourite

Cottage in Ashland

5.0 out of 5 average rating, 41 reviews

Cute vacation rental Mountain View Cottage

Guest favourite

Cottage in Grants Pass

4.93 out of 5 average rating, 56 reviews

Beautiful and Spacious.

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Cottage in Central Point

4.76 out of 5 average rating, 17 reviews

Beautiful cottage w/pool in bamboo forest

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Cottage in Jacksonville

4.84 out of 5 average rating, 58 reviews

Historic Bradshaw House!

Guest favourite

Cottage in Jacksonville

5.0 out of 5 average rating, 29 reviews

Cottage A is a great getaway

Guest favourite

Cottage in Phoenix

4.9 out of 5 average rating, 322 reviews

The Pear Cottage Where city and country life meet

Guest favourite

Cottage in Phoenix

4.99 out of 5 average rating, 407 reviews

Modern Getaway on Sunflower Farm

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Quick stats about cottage rentals in Ashland

Total rentals
10 properties
Local attractions
Lithia Park, Oregon Shakespeare Festival and Ashland Springs Hotel
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
10 properties include access to Wi-Fi
Total number of reviews
1.9K reviews
Nightly prices starting at
$82 NZD before taxes and fees

Cottage holiday rentals in Ashland

Top-rated cottage rentals in Ashland

Holiday rentals for every style

Cabins

Apartments

Houses

Popular amenities for Ashland cottage rentals

Cottage rentals with a hot tub

Cottage in Grants Pass

Cottage in Talent

Place to stay in Jacksonville

Cottage in Talent

Cottage in Talent

Pet-friendly cottage rentals

Cottage in Ashland

Cottage in Ashland

Cottage in Central Point

Cottage in Ashland

Cottage in Grants Pass

Cottage in Jacksonville

Cottage in Gold Hill

Cottage in Eagle Point

Private cottage rentals

Cottage in Shady Cove

Cottage in Ashland

Cottage in Grants Pass

Cottage in Central Point

Cottage in Jacksonville

Cottage in Jacksonville

Cottage in Phoenix

Cottage in Phoenix

Quick stats about cottage rentals in Ashland

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Total number of reviews

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