Guesthouse holiday 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!

Location · Value · Laundry

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!

Family · Value · Heating

Charming cottage, walk to town.

Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown

Value · Location · Outdoor spaces

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

Value · Location · Pets

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.

Value · Family · Backyard

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

Family · Location · Getting around

La Petite Maison + Hot Tub

Welcome to La Petite Maison! Come take it easy at our unique and tranquil home away from home. Located in the heart of the Applegate with nearby wineries and exquisite views of the mountains. Our guest house is equipped with 1 master bedroom, full kitchen/bath, dining and living room with and private SPA on your very own deck! Only a 10 minute drive from the historic town of Jacksonville. At La Petite Maison you will have the peace and quiet of the country, and all that you may need.

Location · Family · Kitchen

Countryman-Fox Carriage House

Considering the central location of this little gem, it is amazingly peaceful. To add to this charm, the cottage is fresh & bright with a lovely view across the valley. What a joy to walk across the street to the theater & dinner without parking issues. Besides being clean & safe, I like the king size bed, the fireplace, the choice of large tub or shower, the heated bathroom floor, and the little yard, the most. NEW: a high speed (240 volt) charger for EVs. You need an adapter.

Family · Location · Hiking

Cozy Jacksonville Cottage

This cozy, rustic one bedroom cottage (325 sq. ft.) is just a 15 min. walk from downtown Jacksonville (3/4 mile) and 30 min. from Ashland. It has private parking, on the property. The owner is happy w/ pets in the cottage, but needs to know in advance that a pet is coming (maximum 35lbs) too. There isn't a full kitchen but it has a kitchenette with sink, fridge, microwave, hot plate and coffee maker, so cooking basics won't be a problem. Relax in the outside patio in the summer.

Location · Family · Getting around

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1 or 2 guests. Light-filled studio (from two solar tubes) on over 1/3 acre of flowers and fruit trees, three blocks from downtown, and craft foods and wine. Very close and easy access from the highway. Jacksonville is 6 miles, and the Ashland Plaza is 17 miles. Southern OR is filled with playhouses, delicious wine, yummy local restaurants, scenic rivers, and endless wilderness. Come enjoy! We celebrate diversity!

Location · Family · Walkability

Eco-Tiny House in SE Medford

Clean and quiet 200 sq ft. detached guesthouse with kitchenette nestled among vegetable gardens and native wildflower beds. Within walking distance of Asante hospital and several shops and restaurants. Easy access to freeway. 20 minutes from downtown Ashland and Jacksonville and only and 10 minutes from downtown Medford. Off-street parking available. Well-behaved pets welcome. Please no smoking inside the guesthouse or on the property.

Family · Value · View

Private Hot Tub • Near Jacksonville & Wineries

Unwind in your private hot tub after a day exploring historic Jacksonville, Rogue Valley wineries, hiking trails, or downtown Medford. This bright, modern guesthouse features a queen bed, a full-size bed in the upstairs loft, a full kitchen, fast Wi-Fi, a Smart TV, and a private fenced backyard. Enjoy a quiet country setting just minutes from restaurants, shopping, and Southern Oregon’s best attractions.

Value · Location · Backyard