Guesthouse holiday rentals in Jackson County

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Top-rated Guesthouses in Jackson County

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Guest favourite

Guesthouse in Medford

4.96 out of 5 average rating, 256 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

Guesthouse in Medford

4.92 out of 5 average rating, 360 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

Guesthouse in Central Point

4.97 out of 5 average rating, 913 reviews

The West Wing Guest House

Located next to the main home, this detached guest house has a separate driveway/parking & hosts kitchen/living downstairs, with bedroom & bathroom upstairs. We are located 5 miles from Jacksonville, home of the Britt Festival & the best local wineries. About 20 minutes south is the town of Ashland, well known for the Shakespeare Festival. Downtown Central Point is just a mile away, where you will find the renowned Rogue Creamery. The house is also only 10 minutes from the Rogue Valley Airport.

Guest favourite

Guesthouse in Medford

4.98 out of 5 average rating, 636 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

Guesthouse in Medford

4.98 out of 5 average rating, 450 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 favourite

Guesthouse in Medford

4.97 out of 5 average rating, 148 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

Guesthouse in Central Point

4.93 out of 5 average rating, 148 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 favourite

Guesthouse in Eagle Point

4.9 out of 5 average rating, 277 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 favourite

Guesthouse in Jacksonville

4.93 out of 5 average rating, 963 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 favourite

Guesthouse in Medford

4.96 out of 5 average rating, 310 reviews

Cabo Cottage, private guest house.

Discover the charm of this inviting 2-bedroom, 1-bath guest house nestled in a quiet neighborhood, conveniently situated just minutes away from essential amenities, and 15 min from airport, and 6-10 min from local hospitals. Equipped with a well-appointed kitchenette, and washer/dryer for added convenience. The master bedroom features a king-size memory foam bed, while the second bedroom has a queen bed. Enjoy a private driveway and entrance. Extended stay discounts available.

Guest favourite

Guesthouse in Central Point

4.94 out of 5 average rating, 737 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 favourite

Guesthouse in Medford

4.95 out of 5 average rating, 1,165 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.