Guesthouse vacation rentals in Medford

A spacious living room area is highlighted by a brown leather sectional sofa accompanied by two decorative pillows. A light wood coffee table sits in the center, situated on a warm-toned wooden floor. Open doorways lead to other rooms, enhancing the airy feel.

4.94 out of 5 average rating, 654 reviews

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!

The exterior of the unit is shown, featuring a private deck with seating and a view of the surrounding greenery. A well-maintained lawn is visible, along with flower beds and mature trees, which enhance the tranquil country setting.

4.97 out of 5 average rating, 314 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!

4.93 out of 5 average rating, 461 reviews

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

The serene riverbank is lined with lush greenery and tall trees, gently swaying in the breeze. Sunlight filters through the leaves, reflecting softly on the tranquil surface of the Rogue River. A small lawn area invites relaxation, with scenic views of the surrounding nature.

4.96 out of 5 average rating, 135 reviews

New Modern Cottage on the Rogue

With breathtaking views of the Rogue River, our stylish one bedroom offers the perfect blend of luxury and tranquility. Spend your days lounging by the water with a glass of wine. The bedroom features a queen-sized bed with plush linens, and a sliding glass door leading directly to the river. The living area has a comfortable leather sofa and large television. The kitchen is equipped with a large stainless steel refrigerator, microwave/airfryer, Keurig coffee machine, and all of the essentials.

4.98 out of 5 average rating, 779 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.

An inviting two-story guesthouse is visible, featuring a light yellow exterior and a private balcony with white railing. Lush greenery and flowering plants frame the entrance, while a welcoming front porch with seating offers a cozy spot to relax.

4.98 out of 5 average rating, 511 reviews

Comice Valley Inn With E V Charger

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.

Guesthouse in Jacksonville

La Petite Maison + Spa

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.

4.96 out of 5 average rating, 178 reviews

The studio features an open layout with a king bed and a cozy seating area. A flat screen TV is positioned near the fireplace. Natural light streams through multiple windows, illuminating the kitchenette and dining area, which are adjacent to a private outdoor space.

4.99 out of 5 average rating, 190 reviews

C Street Station Cottage

Light, bright and simply gorgeous, this charming studio is just a ten minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon. Tucked into a quiet neighborhood in the Historic Railroad District. The space includes a luxurious king bed. bathroom with shower and tub, fireplace, flat screen Smart TV, washer/dryer, and kitchenette. Large private parking space right by the door and the covered patio includes a dining area and barbeque. Designer inspired.

Guesthouse in Jacksonville

An inviting outdoor patio area is surrounded by greenery, featuring a round table with a floral tablecloth and two green chairs. A large red umbrella provides shade. The cottage's door is framed by a vibrant window box filled with flowers, contributing to a charming ambiance.

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.

4.93 out of 5 average rating, 1209 reviews

The studio features a spacious bed framed with a light wood finish, complemented by soft linens and pillows. A ceiling fan provides airflow, while a Roku TV is mounted on the wall. Natural light filters through large windows with sheer curtains, enhancing the inviting ambiance.

4.99 out of 5 average rating, 236 reviews

Tranquil Studio Near Scenic Redwood Hwy

Tucked amongst the trees, 8 miles west of Grants Pass, this charming studio feels like stepping into a quiet fairytale—birdsong and fresh air welcome you in. Enter through the cottage garden into a warm, thoughtfully designed retreat that balances convenience with nature. Perfect for road trippers or exploring the Redwoods, the studio features a spacious deck overlooking a seasonal pond (dry in summer). Guests who book one night often wish they had stayed longer.

A light-filled kitchen area features modern cabinetry, a central island with seating, and stainless steel appliances. Mirrored panels and a small potted plant add depth to the space. An area rug with intricate patterns enhances the warm atmosphere, while a ceiling fan provides air circulation.

4.94 out of 5 average rating, 880 reviews

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!

4.93 out of 5 average rating, 196 reviews

Hot Tub • Near Jacksonville & Wineries - King Bed

Relax in your private hot tub after exploring historic Jacksonville, Rogue Valley wineries, hiking trails, or downtown Medford. This private guesthouse features a king bedroom, queen loft, full kitchen, fast Wi-Fi, Smart TVs, dedicated workspace, washer/dryer, EV charger, guest bikes, outdoor shower, and fenced backyard. Enjoy a peaceful Southern Oregon stay minutes from restaurants, wineries, Britt Festival, and outdoor adventures.

Popular amenities for Medford guesthouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A charming building features warm wooden siding accented with unique artwork, including tools and crafts, mounted on the exterior. Large windows and a distinct triangular roof shape enhance its rustic appeal. A gravel pathway leads to the entrance, surrounded by landscaped greenery.

4.98 out of 5 average rating, 459 reviews

Laurel Farm's Guesthouse

A cozy cottage exterior is framed by well-maintained grass and landscaping. A wooden bench is positioned on the porch, while a circular patio features a small table and blue chairs, inviting relaxation in the outdoor space.

4.94 out of 5 average rating, 470 reviews

Sweet Vintage Cottage steps from Rogue River

The exterior of The Ashland Cottage is shown, featuring a welcoming sign amidst lush greenery. The cottage’s blue siding and distinctive architectural details are highlighted, while a paved walkway leads to the front entrance, framed by natural foliage.

4.98 out of 5 average rating, 563 reviews

Charming cottage, walk to town.

4.93 out of 5 average rating, 207 reviews

The Cedar Cottage - creekside studio

A spacious area features a queen bed adorned with patterned bedding. Original artwork hangs on the walls, adding color to the bright room. Natural light filters through windows, illuminating the space. A small seating area is visible in the background, providing additional relaxation options.

4.96 out of 5 average rating, 152 reviews

Ashland Artist Country Retreat

A well-lit studio apartment features a spacious bed with light bedding and decorative pillows. A circular dining table surrounded by stools is present, alongside a chair. A mirror and an open closet provide convenience, while artwork adorns the walls, adding a subtle touch of nature.

4.92 out of 5 average rating, 139 reviews

East Medford private studio

4.94 out of 5 average rating, 157 reviews

Neil Creek Cottage

A spacious living room is presented with stylish furnishings, including a gray sofa and a patterned area rug. Natural light filters through the large windows. A spiral staircase leads to the loft above, while double doors open to the outdoor space.

4.99 out of 5 average rating, 688 reviews

Charming Guest House - One block from Downtown!

Guest house rentals with a patio

The entrance to the cottage is framed by a rustic trellis and surrounded by lush greenery. A wooden deck leads up to a white door, providing a welcoming access point. Sunshine filters through the leaves, adding a natural brightness to the scene.

5.0 out of 5 average rating, 300 reviews

Countryman-Fox Carriage House

The exterior of a guest house is shown, featuring a light yellow facade and large windows. A deck with white chairs and a table is visible, surrounded by green grass and landscaping stones. A flowering tree provides shade, complementing the serene outdoor space.

4.9 out of 5 average rating, 195 reviews

Mindy’s Ashland Hideaway

A cozy studio room features a king-size bed with decorative pillows against a deep red accent wall. A small dining table with three stools sits nearby, facing an electric fireplace beneath a wall-mounted television. Light hardwood flooring adds warmth to the space.

4.98 out of 5 average rating, 280 reviews

Courtside Cottage - WalkScore 93 - Dog Friendly

The spacious studio features large windows, allowing natural light and showcasing views of mountains. A queen size bed is complemented by sitting areas with a television and coffee table. A dining bistro table neatly fits in the corner, enhancing the open layout.

4.96 out of 5 average rating, 214 reviews

Modern Airy Retreat - Views, Walk to Everything

A serene riverbank is framed by tall trees, with sunlight filtering through the leaves. A neatly maintained lawn extends toward the water's edge, where smooth stones line the bank. The reflective surface of the river complements the lush greenery, enhancing the natural beauty of the environment.

4.98 out of 5 average rating, 126 reviews

Rogue River Retreat with Views You’ll Never Forget

4.85 out of 5 average rating, 169 reviews

Cozy Mountain Hillside Cabin & Woodland Paradise

5.0 out of 5 average rating, 26 reviews

Peaceful Countryside Stay with Scenic Views

4.97 out of 5 average rating, 37 reviews

The Nest at Highcrest

Guest house rentals with a washer and dryer

A cozy living area features a brown leather sofa paired with a green armchair, arranged around a decorative rug. A flat-screen television is positioned against the wall, complemented by a large window allowing natural light. A potted plant adds a touch of greenery.

4.98 out of 5 average rating, 125 reviews

Historic carriage house close to downtown Ashland

A cozy bedroom features a queen size bed, topped with a white duvet and decorative pillows. Two bedside tables with lamps are situated on either side. Natural light filters in through the window, enhancing the serene ambiance of the space.

4.99 out of 5 average rating, 141 reviews

1 BDRM Cottage-Keyless self check in-Quiet Lane

A cozy living area features a plush beige sofa adorned with decorative pillows. A small round table is centered on a patterned rug. A TV is positioned on an ornate stand near a window, which allows natural light to brighten the space. A work desk and additional decor complete the room.

4.95 out of 5 average rating, 140 reviews

JJ's Loft | Downtown | Large Deck | Kitchenette

A cozy cottage features a welcoming front porch with two colorful chairs. The vibrant yellow exterior is complemented by large windows, allowing natural light to enhance the cheerful atmosphere. A small, decorative sun emblem is positioned above the door, inviting guests into the space.

4.96 out of 5 average rating, 257 reviews

Historic Cottage close to plaza

5.0 out of 5 average rating, 23 reviews

A serene sunroom is presented, featuring two woven seating arrangements with floral cushions. Natural light floods the space through multiple windows adorned with blinds, framing views of the surrounding greenery. A potted flower arrangement adds a touch of color to the warm wood flooring.

Guesthouse in Talent

1910 Orchard Guest House

4.98 out of 5 average rating, 62 reviews

NEW Hot Tub, Patio w/fire table! WiFi! King Bed!

Guesthouse in Jacksonville

The exterior of The Serenity Canyon Cottage is visible, showcasing a quaint wooden structure surrounded by lush greenery. A white picket fence frames the entryway, while a compact deck is adorned with chairs. Sunlight filters through the trees, casting gentle shadows on the path.

Serenity Canyon Cottage >5 min to Jacksonville

4.93 out of 5 average rating, 70 reviews