Guesthouse holiday rentals in Ashland

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.

Our guests arrive at The Ashland Cottage and their first words are almost always the same: "It's gorgeous!" That's because the cottage delivers what Ashland visitors want- comfort, charm and a walkable location just 10 minutes from downtown and OSF theaters. Though newly built, the cottage echoes the Craftsman character of our 1920s main residence. As a fully separate house with its own private entrance, it offers spacious living with high ceilings, abundant natural light and inspiring views.

LocationFamilyGetting around

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

Explore downtown Ashland in a private carriage house! This home was built in 1884 and is on the property of an historic Victorian. Full kitchen with stove, dishwasher and refrigerator. Pellet stove in the living room as well as wall vented heating. Enclosed yard. Separate bedroom and en suite with a tub/shower combo and washer and dryer. Off street parking. HBO and Netflix included. 10 minute walk to downtown Please note the only bathroom is through the bedroom. Dog friendly - no cats please

FamilyValueLong stay

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!

ValueLocationOutdoor spaces

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

LocationFamilyLong stay

4.93 out of 5 average rating, 207 reviews

The Cedar Cottage - creekside studio

This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!

ValueLocationRiver

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.

ValueLocationCheck-in

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

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. NEW: a high speed (240 volt) charger for EVs. You need an adapter.

LocationValueCheck-in

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.

FamilyValueCondition

4.93 out of 5 average rating, 1209 reviews

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, 196 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!

FamilyValueSleep quality

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!

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.

LocationValueCheckout

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.

4.97 out of 5 average rating, 245 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.

FamilyValueBackyard

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

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.

FamilyValueHiking

Popular amenities for Ashland guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly guesthouses

Superhost

4.62 out of 5 average rating, 13 reviews

The Milkhouse

LocationGetting aroundHospitality

4.94 out of 5 average rating, 33 reviews

Boutique Bunkhouse | SweetGrass Farms

LocationFamilyTV

A shaded porch is framed by a red wooden structure, featuring comfortable seating and a potted plant. Flowers and stones line the pathway, enhancing the natural setting. Soft outdoor lighting adds a welcoming touch as the entrance to the cabin is visible in the background.

4.95 out of 5 average rating, 21 reviews

Murphy Creek Cabin

ValueFamilyBarbecue

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.

4.88 out of 5 average rating, 26 reviews

Quiet, Private Guest House

LocationValueHospitality

The living area features a dark leather couch adorned with blue accent pillows, a textured ottoman, and area rugs. A small dining table is situated near the entrance, with a chalkboard wall displaying information. A door leads to the semi-private outdoor space.

5.0 out of 5 average rating, 51 reviews

The West Wing Getaway

ValueLocationQuiet

4.98 out of 5 average rating, 62 reviews

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

ValueLocationNearby

Superhost

A spacious sleeping area features three beds arranged with soft bedding. Natural light floods the room through two large windows, complemented by light curtains. A small desk with a circular mirror and a bedside lamp add functionality to the bright green walls and wood-like flooring.

4.66 out of 5 average rating, 164 reviews

Million Dollar View No city tax! Huge 4k tvs

ValueLocationLong stay

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.

4.97 out of 5 average rating, 92 reviews

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

LocationValueHospitality

Guesthouses with a patio

Guesthouse in Jacksonville

La Petite Maison + Spa

ValueFamilyBreakfast

4.96 out of 5 average rating, 178 reviews

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

ValueFamilyDecor

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, 137 reviews

New Modern Cottage on the Rogue

LocationFamilyComfort

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

ValueFamilyNearby

4.85 out of 5 average rating, 169 reviews

Cozy Mountain Hillside Cabin & Woodland Paradise

LocationValueParking

5.0 out of 5 average rating, 22 reviews

Guesthouse in Talent

Sunflower

LocationOutdoor spacesGetting around

5.0 out of 5 average rating, 26 reviews

Peaceful Countryside Stay with Scenic Views

LocationFamilyQuiet

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.

5.0 out of 5 average rating, 50 reviews

Charming 2BR Carriage House Outside Jacksonville

LocationFamilyOutdoor spaces

Guest house rentals with a washing machine and dryer

4.93 out of 5 average rating, 196 reviews

Hot Tub • Near Jacksonville & Wineries - King Bed

FamilyValueOutdoor spaces

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

ValueLocationTV

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, 141 reviews

JJ's Loft | Downtown | Large Deck | Kitchenette

ValueLocationParking

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

FamilyLocationCheck-in

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

LocationValueHiking

Superhost

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.

4.76 out of 5 average rating, 148 reviews

East Main Downtown Bungalow "C"

ValueFamilyPets

4.97 out of 5 average rating, 37 reviews

The Nest at Highcrest

LocationFamilyQuiet