Vacation rentals in Ashland

The exterior of a café is shown, featuring a light-colored wall and large windows. A wooden door invites entry, accompanied by small tables and chairs placed outside. Leafless trees are visible, with a clear blue sky overhead, enhancing the bright atmosphere.

4.96 out of 5 average rating, 173 reviews

Modern Airy Retreat - Views, Walk to Everything

Enjoy the perfect mix of walkable Ashland and your private, airy, urban hideaway. Set in the historic Railroad District with fabulous cafes, restaurants and shops in the same block and nearby, this modern studio over a detached garage has views of trees or mountains from every window. It's only a 5 minute walk to Downtown and a 10 minute walk to Lithia Park and the Oregon Shakespeare Festival. Should you wish, you could park your car in your dedicated space and not use it again during your stay.

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.

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

4.97 out of 5 average rating, 471 reviews

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

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.

Treehouse in Jacksonville

Natural light fills the studio, showcasing an open living area with a sofa and a small table. Large sliding glass doors reveal a deck surrounded by trees, while a staircase leads to the upper level. Cozy seating nooks invite relaxation.

4.97 out of 5 average rating, 263 reviews

Tree Top Studio

Find your Peace in this cozy light filled studio in the treetops of the Siskiyou mountains. The studio is very private with views in every direction of trees, earth and sky (no other buildings in sight). You have direct access to trails leading to old growth forest and a refreshing year long creek. The studio space is an inspiration for artists and lovers of fine details. The kitchen meets all your basic culinary needs. Living room has cozy nooks. Bedroom upstairs has a comfy queen size bed.

4.97 out of 5 average rating, 215 reviews

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

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.

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.

4.99 out of 5 average rating, 174 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.

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.

5 out of 5 average rating, 131 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.

4.98 out of 5 average rating, 250 reviews

Sunset light filters through the leaves of a nearby tree, illuminating spray from lawn sprinklers in the foreground. A wooden fence lines the scene, with mountains visible in the distance as the sky transitions to soft hues of orange and purple.

Farm stay in Ashland

Kelly’s Carriage House 4 miles from Ashland

The Carriage House is located on Kelly's Farm four miles from the city of Ashland and less than two minutes from Highway 5. This two story home is 440 sq. ft with two sliding glass doors affording a 360 degree view of the mountains and sunset. There is an upstairs and downstairs deck, a propane grill and kitchen is fully furnished, two burners, countertop oven, and rice maker among other things. Set up for three people using two beds. Dogs are welcomed but we don't accept cats.

4.95 out of 5 average rating, 426 reviews

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

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!

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, 597 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.

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.

4.98 out of 5 average rating, 175 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.

4.9 out of 5 average rating, 399 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!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Ashland vacation rentals

Self check-in

Monthly stays

Pet friendly

Laptop-friendly workspace

Air conditioning

Dog friendly vacation rentals in Ashland

4.98 out of 5 average rating, 123 reviews

A comfortably arranged living area is highlighted by a brown leather sofa and a round coffee table atop a plush area rug. Natural light filters through sheer curtains, illuminating the space and a decorative fireplace contributes to the serene environment.

Home in Medford

Charming One

4.96 out of 5 average rating, 144 reviews

A comfortable living area features a grey sofa with orange accent pillows and a light purple armchair. A decorative area rug in rich colors anchors the space. Large windows allow for natural light, complemented by vibrant orange curtains and a wall-mounted TV.

Apartment in Phoenix

5 Star Luxury Southern Oregon Suite

4.79 out of 5 average rating, 109 reviews

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.

Home in Talent

Downtown Talent 2 BR bungalow

4.99 out of 5 average rating, 295 reviews

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

Britt Bungalow in the Heart of Jacksonville

4.98 out of 5 average rating, 253 reviews

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

Rogue River Retreat

4.91 out of 5 average rating, 206 reviews

Cottage in Jacksonville

Cottage on River Farm -Applegate Wine Trail

4.87 out of 5 average rating, 116 reviews

A wooden yurt featuring large windows and a distinctive metal roof stands amidst tall pine trees. The entrance has a double door with glass panels, while a small wooden deck leads up to it. Surrounding greenery provides a serene forest atmosphere.

Yurt in Grants Pass

Yurt on the Applegate

4.98 out of 5 average rating, 158 reviews

A spacious lounge area is highlighted by a comfortable sofa and a stylish round coffee table, with sunlit windows enhancing the ambiance. A dog rests on a plush rug, with a tennis ball nearby, creating a relaxed and inviting environment.

Home in Grants Pass

Peaceful Private Retreat on Rogue River Downtown

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Family friendly vacation rentals in Ashland

4.94 out of 5 average rating, 135 reviews

A charming yellow cottage is surrounded by lush greenery, featuring a welcoming entrance with a wooden door and a small outdoor seating area. The well-maintained garden highlights the tranquil setting, with a pathway leading to the entrance under the shade of trees.

Cottage in Ashland

ABBOTT'S COTTAGES- Lark

4.95 out of 5 average rating, 860 reviews

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

Peace on the Rogue river Studio

4.86 out of 5 average rating, 107 reviews

A rustic cabin with a green metal roof sits surrounded by tall trees and lush grass. A stone fire pit is positioned nearby, accompanied by log seating, offering a peaceful outdoor space for gathering.

Cabin in Medford

Woodland Cottage near Jacksonville Dog Friendly

4.94 out of 5 average rating, 310 reviews

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

Artistic Airstream with panoramic views

4.95 out of 5 average rating, 227 reviews

A large log home is nestled among lush greenery, surrounded by trees. The structure features multiple large windows that allow natural light to fill the interior. The expansive deck is supported by sturdy columns, while a gentle slope leads to the landscape below.

Home in Trail

Log Cabin w/Treehouse & Zip Line on Rogue River

4.96 out of 5 average rating, 331 reviews

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

Historic Stage Coach Stop

4.93 out of 5 average rating, 384 reviews

A long, covered balcony extends from the Loft, featuring a swinging seat for relaxation. The view showcases distant mountains and greenery, with trees lining the perimeter. The wooden floor adds a rustic touch, while the soft evening light creates a calming ambiance.

Loft in Hornbrook

The Green Arrow Loft

Guesthouse in Central Point

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, 797 reviews

BEE WELL Organic Spa Garden Studio w/ Hot Tub

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Vacation rentals with pools in Ashland

Guesthouse in Grants Pass

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.

4.98 out of 5 average rating, 121 reviews

Serene Upstairs Studio with Bath & Kitchenette

4.87 out of 5 average rating, 254 reviews

A vibrant green pool float floats gently on the clear, inviting water of the pool. Sun loungers and shaded umbrellas surround the area, amidst leafy trees providing a natural backdrop. The setting offers a serene atmosphere for relaxation.

Apartment in Ashland

Winner 2024 Best of Ashland! Our Carriage House

4.97 out of 5 average rating, 756 reviews

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

Sunset View Yurt of Applegate Valley with HOT TUB!

Guesthouse in Grants Pass

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.

4.94 out of 5 average rating, 453 reviews

Sweet Vintage Cottage steps from Rogue River

4.92 out of 5 average rating, 177 reviews

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

Broken Chair Ranch

4.85 out of 5 average rating, 33 reviews

A spacious outdoor area features a large in-ground pool surrounded by concrete decking. Several lounge chairs are positioned near the water, complemented by a shaded umbrella. Lush trees and a clear blue sky create a serene backdrop for relaxation.

Home in Central Point

Poolside Retreat W/ Sauna Heart of Wine Country

4.92 out of 5 average rating, 212 reviews

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

Octagon Studio / Beautiful Rogue River property