Vacation rentals in Jackson County

The Hygge Stay in the Heart of Southern Oregon

Pet friendly**Close to the I-5 interstate. Within walking distance to park! This guest house, is filled with natural light making it bright and inviting. Thoughtfully designed with guests in mind, you will have no trouble feeling comfortable with all the amenities you’ll need. *Fun fact**, the night stands in the main bedroom were made in the shop downstairs and designed by husband and I! *Airbnb is above working cabinet shop* Message me if you have any questions, I’ll respond within an hour!

Spa Like Stay at the Britt Bungalow in J’Ville

The Britt Bungalow is an Award Winning boutique style stay in the historical heart of Jacksonville Oregon created and designed by the owner and host. Enjoy a spa like private stay w/ 2 bed, 2 bath cottage with 17' ceilings, fresh flower’s throughout, #1 rated Dreamcloud mattress in Master, fireplaced open living room with an abundance of natural light throughout. You will want for nothing during your stay. Just 2 blocks to the trolly, all the best restaurants, boutiques, Britt Gardens, and more

Angel Crest Casita Guest Suite - East Medford

Enchanting, large, private 1 bedroom guest suite with a view In Upper East Medford. Beautiful, open concept living /dining area has plenty of room to relax and unwind. This space also includes a semi private queen bed. There is a large luxurious shower, kitchenette, and other amenities (microwave, fridge, and coffee maker). Outside there is a large private covered deck with outside seating and a fire pit. Close to wineries, golf, restaurants, and great hiking. This is a non smoking property.

The Greenwood Villa w/wood fire hot tub

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

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.

Modern Tiny House w/ Hot Tub and Putting Green

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.

Peaceful Woodland Cabin Nearby Wagner Creek

Welcome to our cozy cabin, nestled in Oregon’s lush forest beside a seasonal creek. Blending rustic craftsman charm with a bohemian flair, our cabin provides a warm ambiance with a well-equipped kitchenette , living room, and a walnut bar-top dining area. In the mezzanine loft, find an organic queen bed and a workspace with a fold-out futon. Enjoy our wood fired hot tub, Wagner Creek trails, nearby wineries and the Shakespeare festival, offering a mix of nature’s beauty and local culture.

Modern Getaway on Sunflower Farm

Stunning modern getaway on a flower farm with spectacular views. Nestled in the heart of the valley. 15 minutes from Ashland and Jacksonville. Home of Shakespeare and Britt Festivals. Over 6 wineries and a distillery within a 3 mile radius. Bright design with beautiful features. The many windows and French doors offer light in all directions with views of sunflowers, pear orchards and Roxy Ann Peak. One mile from the Greenway, a bike and pedestrian pathway linking Central Point to Ashland.

Suite Comice EV Charging

*NOTE*: We disinfect all surfaces before and after new guests arrive. Studio suite with private entrance. Comfortable, light, clean and airy. Host on location in attached home. Breakfast nook with coffee, and tea. Neighborhood is quiet with shopping and dining not far away. Only one small step into the unit. Also on the property is another 2 bedroom Airbnb unit, Comice Valley Inn, in the event you have a larger party. This is a new listing, so please see some of my many 5-star reviews.

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Eagle’s Nest Cottage | 40 mins to Crater Lake

Rogue River Retreat enjoy a cozy weekend of unplugging and quality time with loved ones! - 60 minutes to Crater Lake National Park - Riverfront retreat on the tranquil Rogue River - Wake up to breathtaking river views - Lounge in the hammock while watching rafters, ducks, and fish drift by - Play Ping-pong - BBQing on the patio - Fishing off the dock (BYO poles) - Cook family meals together - Play board games - Stream movies on the Roku TV

Rogue River Bunkie

Experience modern comfort on the Rogue River at our well-appointed Tiny Home, while being conveniently close to the amenities of Shady Cove. The cabin is a short 300 ft. walk from the river, and the neighborhood has private access to a riverside picnic area and one of the best fishing holes on the Rogue River.