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Guesthouse vacation rentals in Medford

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Medford

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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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.

Guesthouse in Central Point

4.94 out of 5 average rating, 604 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!

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.

Guesthouse in Central Point

4.94 out of 5 average rating, 819 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! HOTTUB CLOSED until mid-September 2025.

Top guest favorite

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.

Guesthouse in Medford

4.97 out of 5 average rating, 288 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!

Top guest favorite

An airy living space is highlighted by large windows that provide abundant natural light and views of the surrounding landscape. A wooden ladder leads to a loft area, while minimal furnishings, including a cozy sofa and a wooden table, create a serene atmosphere.

Guesthouse in Medford

4.93 out of 5 average rating, 410 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

Top guest favorite

A landscaped pathway leads to the entrance of the cottage, bordered by gravel and colorful plants. Two inviting chairs sit to the side, while a small sign indicates the direction to the cottage. The fenced yard offers privacy and a peaceful environment.

Guesthouse in Medford

4.98 out of 5 average rating, 711 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.

The interior of the guesthouse features warm wooden walls and high ceilings, creating a cozy ambiance. A dining table with fresh roses sits on a wooden surface, while a well-equipped kitchen and an inviting sitting area are visible, complemented by natural light from the doorway.

Guesthouse in Eagle Point

4.91 out of 5 average rating, 325 reviews

Free Bird Ranch-Oregon Adventures Home Base

Crater Lake National Park is NOT closed, only the 2 mile walking path that leads to a boat ramp is closed for renovation. The rim drive is open all year round. Find peace and serenity in the Rogue Valley. Enjoy stunning valley, Cascade views, and sunsets from the deck. Minutes from vineyards, a short drive to Table Rocks (10 min) & the Rogue River (2 min). On the way to Crater Lake (50 min) & near Ashland skiing (45 min). Unwind in comfort after your adventures. Long-term inquiries welcome!

The outdoor deck area features a private hot tub surrounded by greenery. A colorful tiled table offers seating, and elegant lighting hangs from the red-beamed roof. The space is complemented by a striking black and white patterned rug, creating an inviting atmosphere for relaxation.

Guesthouse in Jacksonville

4.94 out of 5 average rating, 126 reviews

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.

Top guest favorite

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.

Guesthouse in Grants Pass

4.99 out of 5 average rating, 164 reviews

Tranquil Studio Near Scenic Redwood Highway

The studio offers a perfect balance of proximity to town and the tranquility of nature just 8 miles west of downtown Grants Pass. Enter the unit through a flourishing garden and enjoy a cozy, clean oasis. This is a great stopover for road trippers and a convenient home base for exploring the Redwoods and Rogue River. The unit features a spacious deck overlooking a seasonal pond (dry in summer). If you're seeking peace, quiet, and a restful night's sleep, this is the place for you!

Top guest favorite

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.

Guesthouse in Jacksonville

4.93 out of 5 average rating, 1,092 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.

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.

Guesthouse in Ashland

4.87 out of 5 average rating, 100 reviews

Mindy’s Ashland Hideaway

Detached guest house offers a 5 minute drive to the I5 exit/Tesla Chargers & 10 mins to downtown Ashland. spacious, rural feel nestled by open pasture on a serene 1 acre property, this quiet getaway is great for a relaxing vacation, or a quick recharge! With enough parking for a trailer, boat, or other toys, this could be your spot to refresh on your road trip. Quick access to Oregon Shakespeare Festival , wineries, fishing, hiking, mountain biking, or Skiing in Southern Oregon!

Top guest favorite

A spacious chalet is nestled among lush greenery, showcasing its wooden exterior and large windows. The outdoor seating area with a comfortable sofa arrangement is highlighted on the deck, surrounded by well-maintained landscaping, creating a welcoming outdoor retreat.

Guesthouse in Grants Pass

4.97 out of 5 average rating, 211 reviews

Chalet in the Woods

Welcome to the little Chalet in the beautiful Oregon woods! Come relax and unplug in this charming private guest house situated on 4 acres, just 5 minutes from downtown Grants Pass and 3 minutes from grocery stores and shopping yet you feel as if you are out in the country far removed from anything and everything. This space was created to embody Swiss style living and the details speak to that. Comfortable and efficient.

A welcoming living area features a gray sofa adorned with patterned cushions, complemented by a chic coffee table with a succulent centerpiece. A round mirror and a framed artwork enhance the wall, while a desk with a chair provides a workspace. A light-colored rug adds warmth to the space.

Guesthouse in Central Point

4.92 out of 5 average rating, 166 reviews

Modern Guesthouse w/ Hot Tub, Private Yard & Views

Modern 650 sq ft guesthouse near Medford & Rogue Valley wine country. Bright, private retreat with queen bedroom, loft double bed, walk-in shower, and washer/dryer. Fully equipped kitchen + living area. Private fenced yard with hot tub, outdoor shower, BBQ & patio. Perfect for couples, families, or business travelers. Minutes to wineries, hiking, and downtown Medford with your own entrance, parking & privacy.

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A space thats all yours, with room for everyone

Popular amenities for Medford guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

A cozy cabin interior features warm wooden walls and high ceilings. A spacious bed is positioned near a window, providing natural light. A colorful sofa and a small table with flowers enhance the inviting setting. A decorative rug adds texture to the wooden floor.

Guesthouse in Central Point

4.87 out of 5 average rating, 291 reviews

The Peaceful Log Room: 1 Bedroom Guesthouse

A covered patio is framed by vibrant greenery and features a round table with two chairs, along with a lounge chair. Blue doors lead into the cottage, while stone walls provide texture. The area is brightened by natural light streaming under a partially cloudy sky.

Guesthouse in Ashland

4.81 out of 5 average rating, 460 reviews

Carter Lane Cottage

Top guest favorite

A spacious studio features a large bed with a headboard made of wooden planks. Natural light streams in through the windows, illuminating a seating area with a patterned rug. A round table with a chessboard design is centered in the room, with decorative wall art and a kitchenette visible in the background.

Guesthouse in Grants Pass

4.98 out of 5 average rating, 132 reviews

Serene Upstairs Studio with Bath & Kitchenette

Guesthouse in Medford

4.68 out of 5 average rating, 145 reviews

Million Dollar View No city tax! Huge 4k tvs

Top guest favorite

The kitchenette features vibrant blue cabinetry and a wooden countertop. Equipped with a two-burner gas stove, refrigerator, and various cooking utensils, it offers a functional cooking space. Open shelving displays decorative items and kitchenware, enhancing the practicality of the area.

Guesthouse in Grants Pass

4.98 out of 5 average rating, 51 reviews

Close to Downtown Grants Pass Everything you Need!

Top guest favorite

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.

Guesthouse in Grants Pass

4.98 out of 5 average rating, 418 reviews

Laurel Farm's Guesthouse

Top guest favorite

A warm welcome is extended by the cottage's sign, displaying 'Alice Berry Cottage,' positioned beside a red door. A wreath is subtly adorned on the door, enhancing the inviting entrance to this charming residence.

Guesthouse in Ashland

5 out of 5 average rating, 60 reviews

Alice Berry Cottage

A wooden guesthouse with a sloping roof is nestled among tall trees. A spacious deck surrounds the home, featuring a shaded area and planters with greenery. Sunlight filters through the surrounding foliage, creating a serene outdoor space on the gently sloping terrain.

Guesthouse in Medford

4.99 out of 5 average rating, 109 reviews

Private Casita Hidden Above The Valley

Guest house rentals with a patio

Top guest favorite

A cozy bedroom is showcased, featuring a spacious bed with neutral linens and decorative pillows. A small bench with a basket holding folded towels is positioned near the entryway. A hanging rod with garments can be seen in the closet area, along with a plant adding a touch of greenery.

Guesthouse in Medford

5 out of 5 average rating, 50 reviews

The Peach Pit Inn! A sunny retreat w self check-in

Three stylish pendant lights hang above a kitchen island, illuminating a spacious living area. A large window reveals a view of the pool outside, while natural light floods in, highlighting a comfortable sofa adorned with cushions. A decorative plant sits on the counter.

Guesthouse in Medford

4.91 out of 5 average rating, 23 reviews

Stunning East Medford studio with pool & hot tub

Top guest favorite

A serene river scene captures a wooden dock extending into calm waters, reflecting vibrant pink and orange hues of the sunset. Dense trees line the riverbank, with mountains visible in the background, creating a tranquil setting.

Guesthouse in Grants Pass

4.96 out of 5 average rating, 76 reviews

Spectacular Rogue River views & charm!

A kitchenette area features green cabinetry and a vintage refrigerator. A round counter-height table with four stools is positioned for dining or activities. Appliances include a microwave, convection oven, and coffee maker. An armoire stands nearby, providing additional storage.

Guesthouse in Central Point

5 out of 5 average rating, 21 reviews

Spacious Cottage w/King Bed, Fireplace, 65" TV

Top guest favorite

A cozy living area features a comfortable leather sofa adorned with a green throw. Natural light filters through two windows, highlighting a wooden cabinet and a decorative area rug beneath a rustic coffee table. A large framed photograph adds visual interest to the wall.

Guesthouse in Grants Pass

4.96 out of 5 average rating, 70 reviews

New Modern Cottage on the Rogue

Top guest favorite

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.

Guesthouse in Ashland

5 out of 5 average rating, 144 reviews

C Street Station Cottage

Top guest favorite

An inviting living room features a central fireplace with a circular mirror above it. Flanking shelves are decorated with various items. Comfortable reclining chairs offer a cozy seating option. A large television is mounted on the wall, accompanied by a light area rug and natural wood flooring.

Guesthouse in Central Point

5 out of 5 average rating, 12 reviews

2 Bedroom Carriage house

Top guest favorite

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.

Guesthouse in Ashland

4.98 out of 5 average rating, 212 reviews

Courtside Cottage - WalkScore 93 - Dog Friendly

Guest house rentals with a washer and dryer

Top guest favorite

A charming entrance features a bold red door and two red metal chairs situated at a small table, surrounded by gravel and greenery. A modern light fixture is mounted beside the door, adding a welcoming touch to the exterior.

Guesthouse in Ashland

4.98 out of 5 average rating, 190 reviews

Manzanita Cottage

Top guest favorite

The modern guesthouse features a stone-finished exterior with a spacious front entry. A large garage is visible below, while a covered balcony with railing enhances the upper level. Natural surroundings highlight the rural charm, with steps leading up to the entrance.

Guesthouse in Gold Hill

4.97 out of 5 average rating, 92 reviews

Rogue River Guesthouse: Rural river views near I-5

A cozy living room space features a plush gray sofa adorned with decorative pillows. Natural light enters through two windows dressed in light curtains, illuminating a small coffee table and a potted plant positioned beside the sofa. A ceiling fan and wall-mounted TV complete the room.

Guesthouse in Medford

4.9 out of 5 average rating, 97 reviews

Near Downtown- Kitchen-Washer/Dryer-Parking

Top guest favorite

A cozy living area features a blue sofa adorned with colorful pillows, situated next to a wooden coffee table. A wood stove provides warmth, complemented by large windows draped in floral curtains, allowing natural light to fill the space. A staircase spirals elegantly in the background.

Guesthouse in Grants Pass

4.98 out of 5 average rating, 251 reviews

Sand Creek Cottage

Top guest favorite

A comfortable living area is featured, featuring a dark leather sofa, a light beige couch, and a flat-screen TV mounted on the wall. Natural light enters through a large window overlooking greenery, while a private entrance leads outside.

Guesthouse in Eagle Point

4.94 out of 5 average rating, 18 reviews

Deer Ridge Guesthouse

Top guest favorite

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.

Guesthouse in Grants Pass

4.99 out of 5 average rating, 110 reviews

1 BDRM Cottage-Keyless self check in-Quiet Lane

A cozy living room is presented, featuring a dark grey sofa, a small round black table, and a textured pouf. A woven rug with warm tones adds a decorative element. Natural light filters through large windows adorned with simple white blinds, highlighting a plant and wall decor.

Guesthouse in Ashland

4.78 out of 5 average rating, 127 reviews

East Main Downtown Bungalow "C"

Top guest favorite

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.

Guesthouse in Ashland

4.97 out of 5 average rating, 224 reviews

Historic Cottage close to plaza

Quick stats about guesthouse rentals in Medford

Total rentals
30 properties
Nightly prices starting at
G$12,549 GYD before taxes and fees
Total number of reviews
5.8K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

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