Holiday rentals with outdoor seating in Jackson County

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Top-rated rentals with outdoor seating in Jackson County

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

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Guest favourite

Cottage in Grants Pass

4.96 out of 5 average rating, 221 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

Guest house in Medford

4.96 out of 5 average rating, 252 reviews

Mel-Ohana: your favorite country retreat!

Mel-Ohana is a quiet, private two bedroom, 1 bath upstairs unit with comfortable queen memory foam mattresses, kitchen amenities, and a beautiful large bathroom with tiled shower. Open, bright and airy, the country views are spectacular from both bedrooms. It's the perfectly-placed retreat, with Jacksonville/Britt 5 mins away, Ashland -25 mins., and 12 mins. from Medford shopping and restaurants. Wander the 1/2 acre lawn and garden area or share a bottle of wine on the ground-level cedar deck!

Guest favourite

Yurt in Eagle Point

4.97 out of 5 average rating, 231 reviews

Starlight Meadow Yurt

The yurt is a modern, light, space with a deck. It's nestled between a mixed conifer forest and Starlight Meadow. We're at the end of a private road on 20 acres. The property is gated for your comfort and peace of mind. There's a large trampoline at the edge of the meadow perfect for stargazing and sunsets. The creek flows October thru June depending on rainfall. Six miles from Shady Cove where you'll find restaurants and a grocery store. 40 miles to Crater Lake. 26 to Ashland. Treat yourself!

Guest favourite

Guest house in Medford

4.92 out of 5 average rating, 359 reviews

The Greenwood Villa

The guest house, we affectionately call the Villa, is situated near great views, restaurants, wineries, and nature trails available in Jacksonville, Ashland and Medford. Located in the country with views of the famous pear orchards. We have designed the Villa to be a quiet retreat that offers some unique features, so please familiarize yourself with our Property and House Rules. Every detail invites you to slow down and enjoy the beauty of Southern Oregon. Find us on socials: @thegreenwoodvilla

Guest favourite

Guest house in Medford

4.98 out of 5 average rating, 631 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.

Guest favourite

Home in Trail

4.95 out of 5 average rating, 220 reviews

Log Cabin w/Treehouse & Zip Line on Rogue River

Serene, large log home in the woods w/matching tree house fort. Located in Trail, Oregon on 120 acres of forest views and has a 1/2 mile of river frontage on the wild and scenic Rogue River. The property is near to several lakes, waterfalls and scenic hiking trails and is located directly on the way to Crater Lake National Park. Home is located at the end of the road and provides lots of privacy, peace and quiet. The nearby river can be heard from the cabin providing a peaceful environment.

Guest favourite

Tiny home in Shady Cove

4.96 out of 5 average rating, 251 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.

Guest favourite

Guest house in Medford

4.97 out of 5 average rating, 146 reviews

The Loft at Highcrest

The Loft at Highcrest is a wonderful hideaway to relax and unwind with all the amenities of home. We've taken extra care in creating a versatile space filled with natural light that includes two outdoor areas to lounge in. Guests will have full use of laundry facilities, wi-fi and a complete kitchen. At 1,000 sqft there's plenty of room to stretch out. The Loft is situated just minutes from wineries, amazing restaurants and shopping. This is a pet and smoke free loft and property.

Guest favourite

Farm stay in Eagle Point

4.94 out of 5 average rating, 261 reviews

Shadow Bear Lodge - Crater Lake Home Base!

We designed an incredible comfy studio-the Shadow Bear Lodge, perfect for a weekend get away! On the path to CRATER LAKE (50 MIN TO ENTRANCE). This private space offers serenity, comfort and peace away from home. Enjoy beautiful SUNSETS and breath taking MOUNTAIN VIEWS of Table Rock and the Cascades on the private patio. The ROGUE RIVER is minutes away to enjoy fishing. Hiking is popular all around us with the table rocks only minutes away. Or enjoy a glass of wine from Vineyards near by!

Guest favourite

Guest house in Eagle Point

4.9 out of 5 average rating, 274 reviews

Free Bird Ranch-Oregon Summer Adventures Home Base

You’ll love the peace and serenity this private guest house brings! We are minutes away from beautiful vineyards. On the path- (50 minutes) to CRATER LAKE where you can sightsee, hike, and snow shoe. Go fishing on the Rogue 5 minutes away! Enjoy the deck that overlooks the views of the valley and view’s of the CASCADES AND TABLE ROCK which is a 5 minute drive to the entrance. Ashland ski resort is 45 minutes away. Come back to a relaxing and cozy home after your adventures in the Rogue!

Guest favourite

Home in Trail

4.94 out of 5 average rating, 173 reviews

Eagle’s Nest Cottage | 40 mins to Crater Lake

Only 40 minutes to Crater Lake National Park! Nestled directly on the tranquil Rogue River, this riverfront retreat is the perfect spot for a cozy weekend away. Wake up to breathtaking views and lounge in the hammock as rafters, ducks, and fish drift by. Spend your days unplugging with family and enjoying outdoor activities like ping-pong, BBQing on the patio, or fishing off the dock (BYO poles!). In the evenings make a family meal and play board games or stream a movie on the Roku TV.

Guest favourite

Ranch in Prospect

4.97 out of 5 average rating, 634 reviews

Crater Lake "Bunkhouse" on 100 acre ranch & trails

The private Ranch "BunkHouse" sits on a meadow near the horse paddocks & barn w/ views of valley, mountains, & access to gorgeous woodsy hiking trails. The "BunkHouse" retains the rustic charm of the original Bunkhouse but inside it enjoys new comfort, style & amenities! It's an up-dated large (20X40) open studio/bedrm w/ kitchenette & private bath (clawfoot shower/tub). A king-sized bed & extra twin bed if you have a 3rd traveling w/you, all in one room. Also, TV and WiFi