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Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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

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Top guest favorite

A close-up view of a chicken is framed by a wire mesh fence, showcasing its vibrant feathers and prominent comb. Another chicken is partially visible in the background, contributing to the rustic atmosphere of the setting.

Guesthouse in Ashland

4.98 out of 5 average rating, 501 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

Top guest favorite

A combined laundry unit is visible, with a washing machine and dryer stacked. The adjacent bathroom area features a white sink with a wall-mounted mirror, a toilet, and a wooden chair positioned nearby. Soft lighting enhances the workspace.

Cottage in Ashland

4.97 out of 5 average rating, 470 reviews

Victorian Garden Carriage House

You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.

A modern bathroom showcases a large copper soaking tub, complemented by decorative floral wallpaper that adds visual interest. Natural light enters through the window, illuminating the space. A small side table holds neatly arranged toiletries, enhancing the functional yet stylish atmosphere.

Apartment in Ashland

4.97 out of 5 average rating, 214 reviews

Moody Ashland Escape: Luxe Suite, Copper Tub

Welcome to the Premier Suite @ The Matriarch, a historic heritage property in downtown Ashland. This self check-in style accommodations means you have the place all to yourself. Stroll to dinner at one of Ashland's finest restaurants or cozy up in the private outdoor living room. Expect thoughtful local touches and attention to every last detail. Soak in the beauty of bold design as you decompress in our generous copper tub. The Matriarch is our newest addition to the Swank House family.

Top guest favorite

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.

Guesthouse in Ashland

4.99 out of 5 average rating, 595 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.

Top guest favorite

A spacious bedroom is showcased with natural light flowing through large windows. A king-sized bed is centered, accompanied by nightstands and lamps. A modern wardrobe and an ottoman add functionality. A cozy chair is positioned near the window, providing comfortable seating.

Guesthouse in Ashland

4.99 out of 5 average rating, 172 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

A spacious studio features a king bed with neatly arranged bedding in muted tones. A comfortable armchair in a vibrant pattern adds color to the room. Natural light flows in from large glass doors that open to an outdoor area with a dining set.

Guesthouse in Ashland

5 out of 5 average rating, 130 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.

A gated entrance features stone pillars and wrought iron gates, surrounded by lush greenery. Pathways lined with trees can be seen beyond the gate, creating a sense of privacy and seclusion for the property.

Cabin in Ashland

4.95 out of 5 average rating, 423 reviews

Studio Cottage near downtown Ashland - Queen Bed!

Take it easy at this unique and tranquil small studio cottage getaway. Our guest cabin has remodeled upgrades and is perfectly located minutes off the 5 freeway and just 3 miles from downtown Ashland's Shakepeare Fetival, Plaza shops, beautiful Lithia Park and Resturants. Venture to local lakes including Crater Lake, historic Jacksonville, and wineries in the pituresque Rogue Valley from our central location. Enjoy the privacy of our gated property with peaceful surroundings!

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, 173 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)

A scenic view is presented from the open door, showcasing a pathway of stone leading through a lush garden. Green grass and vibrant foliage surround the area, with wooden decking seen at the entrance. Decorative rugs add color and warmth to the entryway.

Guesthouse in Ashland

4.9 out of 5 average rating, 398 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 deck is shown featuring a comfortable seating arrangement made of woven material. The area is adorned with a table, colorful flowers, and string lights overhead. Expansive views of rolling hills and greenery create a serene backdrop.

Home in Ashland

4.96 out of 5 average rating, 222 reviews

Coyote Moon

Beautiful 1360 square foot home on 2 acres. Modern, shed roof design with great windows and view of Grizzly Peak. Quiet and peaceful but only 1.8 miles from the heart of downtown Ashland. Deck with propane fire table. Kitchen with quartz countertops and island. Perfect for a romantic couples getaway and also great for those visiting Ashland for the Oregon Shakespeare Festival. Wireless internet and Netflix and internet TV.

A compact kitchen area features modern cabinetry with a neutral color scheme. Basic appliances, including a coffee maker and hot plate, are available. The bamboo flooring adds warmth to the space, and a door leads to a small bathroom area, creating a functional layout.

Guest suite in Ashland

4.9 out of 5 average rating, 114 reviews

Summer’s Night Cottage 8 minute walk to Downtown

Clean and comfortable cottage perfect for a getaway. Short distance to downtown Ashland, Lithia Park, Oregon Shakespeare Festival, and more. Great outdoor space. Relax in our clean 1 bedroom cottage with a newer queen bed, high thread count sheets, and convertible full size sofa, sleeping area. Walk to one of the many restaurants & bars or fix a simple meal with provided hot plate and kitchen basics.

A well-maintained garden is visible, featuring lush green grass and neatly arranged pathways. Vibrant shrubs and trees, including a red foliage tree, create a serene outdoor space. The property’s architecture includes shaded porches, enhancing the inviting character of the area.

Bungalow in Ashland

4.9 out of 5 average rating, 145 reviews

ABBOTT'S COTTAGES - Cardinal

Enjoy breakfast with the hummingbirds on the redwood deck surrounded by wisteria and trumpet vines. This bright and cheery cottage has a cozy queen bed, a queen size hide-a-bed in the living room and a fully equipped kitchen. Short walk to theatres. There are other cottages on the property if you are with a group looking for more than one house. Just let us know!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Ashland vacation rentals

Laptop-friendly workspace

Air conditioning

Dog friendly vacation rentals in Ashland

Top guest favorite

The exterior of a cob cottage is displayed, showcasing a green door with glass panels and three tall windows. A single red chair is positioned near the entrance, surrounded by natural elements, including stones and shrubs that enhance the rustic ambiance.

Earthen home in Wolf Creek

4.88 out of 5 average rating, 375 reviews

The Nest Eco-Retreat Cob Cottage

Top guest favorite

A spacious dining area features a large wooden table surrounded by six chairs. Natural light fills the room through two large glass doors that open to a deck with forest views. A bowl sits at the center of the table, adding a welcoming touch.

Home in Gold Hill

5 out of 5 average rating, 175 reviews

Hygge Hideaway. A home for rest and adventure

Top guest favorite

A spacious studio is presented with a comfortable bed adorned with accent pillows. A kitchenette is equipped with a refrigerator and compact appliances. A seating area with two chairs and a side table complements the inviting space, which benefits from ample natural light.

Guest suite in Medford

4.94 out of 5 average rating, 138 reviews

Clean & Private E. Medford Studio with own W/D

Top guest favorite

A bright living room features large windows that allow abundant natural light, complemented by a comfortable brown sofa and a cozy armchair. Lush green plants add a touch of nature, while a simple coffee table rests atop a textured area rug.

Home in Jacksonville

4.99 out of 5 average rating, 295 reviews

Britt Bungalow in the Heart of Jacksonville

A wooden deck extends along the riverbank, framed by lush green trees. Two chairs provide seating for relaxation, while flower pots add a touch of color. The tranquil water reflects the surrounding nature, creating a serene atmosphere ideal for enjoying the outdoors.

Home in Gold Hill

4.98 out of 5 average rating, 250 reviews

Rogue River Retreat

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, 242 reviews

Sand Creek Cottage

Cottage in Jacksonville

4.91 out of 5 average rating, 206 reviews

Cottage on River Farm -Applegate Wine Trail

An entryway is visible, featuring an open door leading to the outside and a black garment rack with clothes hangers. Two wooden stools are positioned at a small table, alongside dining ware. A bathroom is partially shown through a doorway, and a glimpse of green grass and a fence is visible outside.

Guesthouse in Medford

4.95 out of 5 average rating, 367 reviews

Modern, pet-friendly, private - EV charger level 2

Family friendly vacation rentals in Ashland

Top guest favorite

A serene pond surrounded by vibrant autumn foliage reflects hues of red, yellow, and green. The trees frame the water's edge, creating a peaceful natural setting highlighted by scattered leaves floating on the surface.

Apartment in Ashland

4.87 out of 5 average rating, 254 reviews

Winner 2024 Best of Ashland! Our Carriage House

The exterior of the Ivy Cottage is framed by lush greenery and trees. A covered porch with seating is visible, inviting outdoor relaxation. A stone pathway leads up to the home, flanked by decorative rock borders and garden features, offering a charming and welcoming entrance.

Home in Jacksonville

4.97 out of 5 average rating, 290 reviews

Ivy Cottage

A simple living space features a navy sofa with coordinating cushions and a wooden coffee table. A patterned chair and a small side table are positioned nearby. Light-colored walls are complemented by artwork, and a cozy rug covers the floor.

4.79 out of 5 average rating, 109 reviews

Downtown Talent 2 BR bungalow

A spacious bedroom features a comfortable bed with soft linens, accented by orange and neutral pillows. Large windows with decorative curtains allow natural light to flood the room. A wooden table and folding chairs provide additional seating, and a ceiling fan offers air circulation.

Apartment in Ashland

4.88 out of 5 average rating, 795 reviews

Clean, Stylish Apt w/kitchen. block from Downtown

Top guest favorite

A 1977 Airstream trailer is prominently positioned on a gravel path with a scenic backdrop of greenery and distant hills. The trailer's gleaming exterior reflects sunlight, complemented by trees and a private seating area with potted flowers nearby. The setting provides a tranquil atmosphere amidst nature.

Farm stay in Talent

4.94 out of 5 average rating, 310 reviews

Artistic Airstream with panoramic views

Top guest favorite

A charming two-story house is set amidst lush greenery, featuring a balcony with white railings. Brightly colored flowers surround the patio area, and a decorative wall art piece is visible near the entrance. The soft blue sky complements the light yellow exterior.

Guesthouse in Medford

4.95 out of 5 average rating, 183 reviews

Comice Valley Apartment with EV Charger

Top guest favorite

The exterior of the brick cottage is framed by lush greenery and vibrant flowers, creating a serene garden setting. A wooden pergola extends from the cottage, providing shade over a small patio with a table and chair, inviting moments of relaxation outdoors.

Bungalow in Ashland

4.96 out of 5 average rating, 331 reviews

Historic Stage Coach Stop

Top guest favorite

A cozy living area features light green walls and a comfortable seating arrangement, complemented by a floor lamp. A decorative electric fireplace adds warmth, while large windows allow natural light to fill the space. A small dining table for two is positioned nearby.

Bungalow in Ashland

4.9 out of 5 average rating, 132 reviews

Railroad Cottage at Chozu Gardens

Vacation rentals with pools in Ashland

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, 120 reviews

Serene Upstairs Studio with Bath & Kitchenette

Top guest favorite

The exterior of the yurt is highlighted by warm light emanating from the windows, creating a welcoming ambiance in the evening. A wooden deck leads to the entrance, while a nearby chair rests under a small tree. Soft landscaping and a hammock are visible in the background.

Yurt in Grants Pass

4.97 out of 5 average rating, 755 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

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, 453 reviews

Sweet Vintage Cottage steps from Rogue River

A clear blue swimming pool is framed by a wooden deck and green trees, offering a refreshing ambiance. Lounge chairs are positioned along the poolside, and a covered seating area is visible in the background, providing shade and comfort.

Apartment in Medford

4.92 out of 5 average rating, 177 reviews

Broken Chair Ranch

Top guest favorite

A lush green lawn is complemented by two metal chairs and a circular table, inviting relaxation outdoors. A wooden deck by the river features a seating area surrounded by trees, creating a serene space for enjoying the natural surroundings.

Apartment in Grants Pass

4.95 out of 5 average rating, 860 reviews

Peace on the Rogue river Studio

Top guest favorite

A small stock tank pool is surrounded by tall trees, offering a serene outdoor setting. Inflatable pool floats are visible, including a flamingo and a unicorn. A shaded area provided by a striped umbrella enhances the relaxing atmosphere.

Cabin in Grants Pass

4.97 out of 5 average rating, 244 reviews

Tiny Cottage w/Firepit/Hottub/Outdoor tubs

An inviting bedroom features a spacious bed with light-colored bedding, positioned beneath a sloped wooden ceiling. Large windows provide natural light and a view of the surrounding greenery. A decorative wooden dresser and a small table add functional charm to the room.

Guest suite in Gold Hill

4.92 out of 5 average rating, 212 reviews

Octagon Studio / Beautiful Rogue River property

Four orange Adirondack chairs are arranged on a grassy area, facing a wide, open view of a distant mountain landscape. A clear blue sky scattered with white clouds creates a serene backdrop, while leafy branches frame the scene.

Guest suite in Jacksonville

4.85 out of 5 average rating, 240 reviews

Scenic and relaxing roadtrip stop-over!

Quick stats about vacation rentals in Ashland

Total rentals
340 properties
Total number of reviews
22K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Ashland?
Yes! Work meets play with ease at over 170 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cottage rentals in Ashland?
Experience the best of Ashland with our cottage rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Ashland?
Four-legged friends are welcome in Ashland. Choose from more than 130 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Ashland?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with self check-in, over 100 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do private suite rentals in Ashland have air conditioning?
Absolutely! We offer over 30 private suite rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.
Are there Ashland boutique hotel rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 boutique hotel rentals with pools in Ashland, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Ashland have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Ashland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Ashland?
Ashland has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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