Guesthouse vacation rentals in Jackson County

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Top-rated guesthouse rentals in Jackson County

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Guest favorite

Guesthouse in Medford

4.92 out of 5 average rating, 367 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 favorite

Guesthouse in Medford

4.98 out of 5 average rating, 647 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 favorite

Guesthouse in Medford

4.98 out of 5 average rating, 454 reviews

Comice Valley Inn (Sanitized Daily)

Health care professionals please ask about special rate for longer term rental. We disinfect all surfaces before and after new guests arrive. Rest assured. Comfortable, light, clean and airy private two bedroom upstairs guesthouse. Host on location in separate home. Fully equipped kitchen, with breakfast provided, makes this the perfect place for overnight or an extended stay. Neighborhood is quiet and shopping and dining are not far away. Two bedrooms make this a perfect getaway for friends.

Guest favorite

Guesthouse in Medford

4.97 out of 5 average rating, 152 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 favorite

Guesthouse in Central Point

4.92 out of 5 average rating, 152 reviews

Hot tub - Modern - Relaxing - Private - Clean

Our cozy, modern guest house is light, open and spacious. It is approximately 650 sq ft with Hot Tub, 1 queen bedroom, a cozy upstairs loft with a double bed. The bathroom has a walk in shower, washer & dryer. Fully equipped kitchen that flows into the dining and living room. Off the dining area is a private yard with patio, hot tub, outdoor shower, BBQ, chairs and table . Our guest house is located behind a detached shop so you'll have a private entrance & convenient parking and privacy.

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 557 reviews

Charming Guest House - One block from Downtown!

This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.

Guest favorite

Guesthouse in Eagle Point

4.9 out of 5 average rating, 287 reviews

Free Bird Ranch-Oregon 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 favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 113 reviews

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. Charging is available for your electric cars in the upper parking area.

Guest favorite

Guesthouse in Jacksonville

4.93 out of 5 average rating, 979 reviews

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.

Guest favorite

Guesthouse in Central Point

4.94 out of 5 average rating, 752 reviews

BEE WELL Organic Spa Garden Studio w/ Hot Tub

This detached 420 sf apartment is perfect for 1-2 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 miles of wilderness. Come enjoy! We celebrate diversity!

Guest favorite

Guesthouse in Medford

4.96 out of 5 average rating, 1,178 reviews

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.

Superhost

Guesthouse in Jacksonville

4.96 out of 5 average rating, 151 reviews

Valhalla Cabin, King Bed, Hiking, close to Britt

Tranquility & hiking. 128 AC of wooded acreage to hike on. The flowers bloom in the spring! Come and see! We are located about 20 min from The Britt in Jacksonville. Check out their venue and list of performers! ***This is a NO SMOKING IN OR OUT of the unit/property, This cabin is NOT suitable for children, No animals allowed EXCEPT for service dogs. When there is snow, 4-wheel vehicles are advised***