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Guesthouse vacation rentals in Ashland

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Top-rated guesthouse rentals in Ashland

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

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Top guest favorite

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.

Guesthouse in Ashland

4.98 out of 5 average rating, 507 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

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, 400 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 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, 101 reviews

1 BDRM Cottage-Keyless self check in-Quiet Lane

Beautiful, fully furnished, 460 sq feet, one bedroom apartment with all the amenities. Private keypad entrance and dedicated parking space. Ideal for traveling professionals who need a short term rental or those looking for a vacation rental. Great location near the river and parks. Walking distance to town. The bedroom has a queen size bed. The open concept kitchen/living room has a queen size sofa sleeper. Full kitchen. Washer and dryer. Outside sitting area with BBQ. Hi-Speed Wifi.

Top guest favorite

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.

Guesthouse in Ashland

4.99 out of 5 average rating, 183 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.

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, 136 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.

Top guest favorite

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.

Guesthouse in Ashland

4.99 out of 5 average rating, 604 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 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.

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, 216 reviews

Historic Cottage close to plaza

Whimsical, cozy cottage located off quiet alley behind our main residence. Low-key, friendly neighborhood in the Skidmore Historic District. Front porch and back patio. Park your car and never get back in until it's time to leave. Street parking with a walk of about 250 feet to the cottage. Just 4 blocks from downtown. Full kitchen & laundry. A light-filled groovy hideaway. (Our wifi is good, but if you are doing zoom meetings, don't expect perfection.)

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, 180 reviews

Manzanita Cottage

Enjoy staying in this newly-constructed cottage in the heart of Ashland's historic railroad district. Park your car and enjoy all that Ashland has to offer by foot. Easy walking distance to downtown shops and restaurants, OSF, Lithia Park and the Ashland Food Coop. Outdoor enthusiasts can start their mountain biking, running or hiking adventures right from their door. Your hosts can help to point you in the right direction. (Permit #: PA-2018-00531)

Top guest favorite

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, 809 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!

A stone pathway leads through a lush garden filled with vibrant flowers, including pink roses, towards a charming cottage. The garden is surrounded by greenery and features an archway, adding a picturesque framing to the entrance.

Guesthouse in Ashland

4.9 out of 5 average rating, 402 reviews

Private Garden Cottage w Sauna in RR District

Located in the historic Railroad District, our cottage is walking distance from the Shakespeare theater and all the trimmings of downtown. Walk to an award winning coffee shop down the alley and two grocery stores and park. Set between the cottage and our house are beautiful vegetable and flower gardens. There is a great deck for morning coffee and secure bike storage available. Miles of mountain hiking trails are close by. This will be your new spot!

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, 204 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.

Top guest favorite

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.

Guesthouse in Ashland

4.95 out of 5 average rating, 125 reviews

Ashland Artist Country Retreat

Lovely light-filled, artistic, private, quiet, two-level studio apartment with full bath and kitchenette located on an organic farm in a beautiful country setting, just 3.6 miles to downtown Ashland and the Oregon Shakespeare Festival. Enjoy a private garden and views of the trees and mountains, as well as original art made by your host. We offer organic and upscale amenities and use only eco-friendly and healthy cleaners.

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

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A space thats all yours, with room for everyone

Popular amenities for Ashland 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

Top guest favorite

A living room is presented with a large down-filled sectional sofa and a glass coffee table. A flat-screen TV is positioned on a wooden stand, complemented by a decorative lamp. Sliding glass doors open to a view of the garden, allowing natural light to fill the space.

Guesthouse in Gold Hill

4.74 out of 5 average rating, 64 reviews

Dream Cottage on the Rogue River

Guesthouse in Medford

4.67 out of 5 average rating, 143 reviews

Million Dollar View No city tax! Huge 4k tvs

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, 90 reviews

Rogue River Guesthouse: Rural river views near I-5

A warm kitchen area features wooden cabinetry and stainless-steel appliances. A counter with two stools offers seating. Natural light enters through a window adorned with floral curtains, and a water cooler stands nearby, providing easy access to drinking water.

Guesthouse in Medford

5 out of 5 average rating, 5 reviews

Quiet, Private Guest House

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.

Guesthouse in Grants Pass

4.94 out of 5 average rating, 454 reviews

Sweet Vintage Cottage steps from Rogue River

A private outdoor patio is surrounded by lush greenery, featuring a table with four chairs. Natural light filters through the leaves, creating a serene space accentuated by an overhead trellis.

Guesthouse in Ashland

4.86 out of 5 average rating, 148 reviews

ABBOTT'S COTTAGES- Egret

The two-story house features a light-colored exterior with large windows and a spacious balcony. Lush greenery surrounds the entrance, while a patio umbrella and seating are visible on the balcony. The driveway leads to a well-maintained garden area.

Guesthouse in Medford

4.96 out of 5 average rating, 70 reviews

Roxy Ann Retreat - Large Luxury Carriage House

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, 44 reviews

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

A cozy sitting area features a bay window with natural light flooding in. A plush blue chair is paired with a green cushioned bench and a glass coffee table. A bouquet of flowers adds a pop of color, complemented by a mounted television displaying serene landscapes.

Guesthouse in Ashland

5 out of 5 average rating, 16 reviews

Hanna's House by WanderLodges |1 block to downtown

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

4.96 out of 5 average rating, 115 reviews

La Petite Maison + Hot Tub

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, 22 reviews

New build in East Medford with pool & hot tub

Top guest favorite

A spacious studio room is presented with a queen bed featuring a patterned gray and white bedspread. A fold-out couch is positioned nearby. Natural light enters through multiple windows, while a door leads outside. Decorative art frames are mounted on the walls, adding visual interest.

Guesthouse in Ashland

4.95 out of 5 average rating, 41 reviews

Silver Frog Guesthouse- downtown Ashland 'hood

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

4.95 out of 5 average rating, 65 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, 20 reviews

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

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

4.95 out of 5 average rating, 58 reviews

New Modern Cottage on the Rogue

Guest house rentals with a washer and dryer

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

5 out of 5 average rating, 13 reviews

1910 Orchard Guest House

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

4.95 out of 5 average rating, 592 reviews

The Hygge Stay in the Heart of Southern Oregon

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

4.89 out of 5 average rating, 92 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, 247 reviews

Sand Creek Cottage

The exterior of a charming green house features a large entry with double wooden doors and decorative overlays. A pergola with climbing elements provides partial shade. A small garden area with low-maintenance landscaping is visible in front, complemented by a stone walkway.

Guesthouse in Jacksonville

4.8 out of 5 average rating, 10 reviews

The Springs - a place to grieve, heal and refresh

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, 163 reviews

Hot tub - Modern - Relaxing - Private - Clean

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

4.79 out of 5 average rating, 122 reviews

East Main Downtown Bungalow "C"

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.

Guesthouse in Ashland

4.93 out of 5 average rating, 45 reviews

Historic carriage house close to downtown Ashland

Quick stats about guesthouse rentals in Ashland

Total rentals
20 properties
Nightly prices starting at
G$12,532 GYD before taxes and fees
Total number of reviews
3.2K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

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