Guesthouse vacation rentals in Ashland

Guesthouse in Eagle Point

A wooden door opens into a serene space featuring a sauna, constructed with warm-toned wood. Soft lighting illuminates the interior, highlighting towels neatly placed within the sauna. A decorative vase with slender plants stands on the floor, adding a touch of elegance to the area.

4.91 out of 5 average rating, 304 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 River, minutes away! Enjoy the deck that overlooks the views of the valley and views of the CASCADES. Hike the TABLE ROCKS, 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 Valley.

Guesthouse in Central Point

A modern kitchen and dining area is highlighted by a wooden table, set with a simple vase of flowers. Ample natural light enters through large windows, while sliding glass doors lead to an outdoor space. Stylish pendant lights provide functional illumination.

4.95 out of 5 average rating, 576 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 bright living area features a comfortable white sofa and a small round table. Large sliding glass doors lead to an outdoor deck surrounded by trees. Natural light fills the space, highlighting the warm wood tones of the flooring and ceiling.

4.98 out of 5 average rating, 492 reviews

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

4.98 out of 5 average rating, 674 reviews

A gravel pathway leads to a cozy seating area featuring a wooden bench and surrounding greenery. A beige wall and wooden fence create a sense of privacy, while potted plants add a touch of natural beauty to the outdoor space.

Guesthouse in Medford

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.

4.98 out of 5 average rating, 460 reviews

A vibrant red maple tree is central in the garden, surrounded by lush greenery and colorful flowers. The scene is framed by wooden trellises and vines, with soft sunlight illuminating the landscaped area, creating a serene outdoor space.

Guesthouse in Medford

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 Central Point

A light-filled living space features a comfortable gray sofa adorned with decorative pillows and a wooden coffee table. A stylish chair is positioned nearby, and a dining area with a round table is visible in the background. A staircase leads to the upper loft.

4.92 out of 5 average rating, 158 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.

Double wooden doors welcome guests to the entrance, surrounded by potted plants. Light fixtures are mounted on either side, illuminating the entryway. A patterned mat lies in front of the steps, which lead up to the door.

4.99 out of 5 average rating, 582 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.

Guesthouse in Jacksonville

The entrance of the guest house features a welcoming porch adorned with potted plants and flower arrangements. Natural stone steps lead to the door, which is complemented by charming decor. Lush greenery surrounds the area, adding to the tranquil ambiance.

4.95 out of 5 average rating, 107 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.

A spacious studio layout features a comfortable king-size bed, kitchenette with modern appliances, and a decorative mirror. A cozy seating area is created by a velvet chair, and natural light fills the room through multiple windows, enhancing the welcoming atmosphere.

4.99 out of 5 average rating, 150 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.

Guesthouse in Grants Pass

A welcoming porch area is visible, showcasing a yellow-and-white exterior with decorative columns. A neatly paved path leads through a landscaped yard featuring green grass and flower beds. A mature tree stands nearby, and a vehicle is parked in the background.

4.96 out of 5 average rating, 359 reviews

Queen Lady Vacation Rental pet friendly.

Awestruck is not nearly enough to describe what you feel when you see our 1905 Colonial revival home. We have worked tirelessly to restore this home to its original charm. The main rental unit is a private restored two bedroom Carriage house that is fully air conditioned with an open floor plan. We are less than 1 mile from town but still enjoy watching deer families and wild turkeys cross our property. It truly is a home away from home and a clean comfortable place to relax in.

4.88 out of 5 average rating, 143 reviews

A staircase leads up to the studio apartment, with a railing visible on the left. The entrance door is located at the bottom, and light streams in from a skylight above. A Smart TV is positioned on the wall within the studio space.

Guesthouse in Medford

Loft Near Downtown-Studio-Parking -Kitchenette-

Adorable upstairs guest studio apartment. Perfect location within walking distance to downtown, restaurants, farmer's market, shopping, hospitals, park, movie theater & bus lines. Apartment access & private off street parking from the rear alley. This studio includes full bathroom with tub/shower, kitchenette, queen bed, 2 chairs & a large SmartTV Stocked Kitchenette includes mini a fridge, sink, microwave, & supplies for coffee/tea. ***STAIRS REQUIRED***

An aerial view shows a well-stocked kitchen with blue cabinetry and a wooden countertop. A dining table is positioned nearby, with chairs arranged around it. Natural light filters through the windows, illuminating the concrete flooring and highlighting the open layout.