Vacation rentals with outdoor seating in Ashland

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Ashland

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Ashland

4.96 out of 5 average rating, 365 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.

Nov. 29 – Dec. 6

$224 CAD per night

Guest favourite

Apartment in Ashland

4.94 out of 5 average rating, 256 reviews

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (low ceiling) Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Private parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Aug. 4 – 11

$201 CAD per night

Guest favourite

Cottage in Ashland

4.97 out of 5 average rating, 426 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.

Nov. 14 – 21

$338 CAD per night

Guest favourite

Guesthouse in Medford

4.98 out of 5 average rating, 583 reviews

Orchard Home Cottage * ~ Private, Cozy, Peaceful *

*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

May 13 – 20

$133 CAD per night

Guest favourite

Tiny homes in Shady Cove

4.96 out of 5 average rating, 202 reviews

Modern Tiny House w/ Hot Tub

Located on a hillside in Shady Cove. This is a spacious brand new 300 sq foot tiny home. The tiny house is located on our private property. We request for our guests to be respectful of our home, our neighbors, and surroundings. It is important that our guests treat the outdoor space as if they were camping and not leave any food outside as there is some wildlife in the area. Included is a covered gazebo with curtains on a private deck with a spa, and gas fire pit that also heats your legs.

Sep. 17 – 24

$219 CAD per night

Guest favourite

Treehouse in Jacksonville

4.98 out of 5 average rating, 188 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

Aug. 21 – 28

$297 CAD per night

Guest favourite

Cottage in Ashland

4.99 out of 5 average rating, 143 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.

Nov. 19 – 26

$270 CAD per night

Guest favourite

Farm stay in Ashland

4.99 out of 5 average rating, 118 reviews

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

Sep. 3 – 10

$175 CAD per night

Guest favourite

Yurt in Grants Pass

4.97 out of 5 average rating, 656 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

NO CLEANING FEE! Large 24 ft yurt located on our 5 acre horse property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: ONLY well-behaved children are welcome. If your kids are destructive or abusive, you will be asked to leave.

Jan. 24 – 31

$141 CAD per night

Guest favourite

Cabin in Grants Pass

4.98 out of 5 average rating, 413 reviews

The Cozy Cabin (with own private hot tub!)

Come relax and unwind in our cozy, peaceful cabin, tucked away in the beautiful hills of Grants Pass. With mountain views, stunning sunsets and a private wooded environment, it’s the perfect place to get away. Relax, read a good book, take a soak in the hot tub located just steps outside the master suite. The Cozy Cabin is filled with thoughtful touches, from throw blankets to high quality linens and towels, selected to create a welcoming and comfortable atmosphere.

May 27 – Jun. 3

$204 CAD per night

Guest favourite

Camper/RV in Ashland

4.88 out of 5 average rating, 923 reviews

Cozy camping close to town

The 1973 Kit Companion is a 15-foot trailer converted to maximize space and guest experience. Featuring a water dispenser, French press, hot water kettle, lending library, and games; this adorable camper is both functional and gives guests a unique and comfortable space. The “Kit” is small, private, and located conveniently close to Ashland downtown and Interstate 5. Guests who stay in trailer have access to the shared bathroom and shower in the house.

May 28 – Jun. 4

$73 CAD per night

Guest favourite

Home in Ashland

4.95 out of 5 average rating, 180 reviews

Coyote Moon

Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.8 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island. Perfect for a romantic couples getaway and also great for those visiting Ashland for the Oregon Shakespeare Festival. Wireless internet and Netflix and internet TV.

Dec. 31 – Jan. 7

$344 CAD per night