Pet-friendly holiday rentals in Ashland

Farm stay in Jacksonville

The exterior of the modern two-story cottage features a large outdoor deck with steps leading to a landscaped yard. A circular fire pit surrounded by wooden chairs offers a cozy gathering space, while the fenced yard provides privacy and a serene environment.

4.98 out of 5 average rating, 119 reviews

Cozy Family Ranch Cottage! Near Vineyards & Lake!

Welcome to Guches Ranch! Nestled on a picturesque ranch established in 1964 by the Guches family, a vast expanse of lush farmland. Our Airbnb listing is the ultimate retreat for those seeking solace and serenity away from the hustle & bustle of city life. We are located centrally to local popular Vineyards in the serene Applegate Valley, just 12 miles outside the historic Jacksonville Oregon. Our brand new modern-style single cottage is a stand alone unit & is a private cozy, yet spacious haven.

4.97 out of 5 average rating, 488 reviews

The inviting living area showcases a stone fireplace as a focal point, complemented by a wooden mantel. Sunlight filters through large windows, illuminating a seating area with a comfortable chaise lounge and a wooden table. A rich area rug adds warmth to the hardwood floor.

Cottage in Lithia Park

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.

4.99 out of 5 average rating, 141 reviews

The kitchen area features stainless steel appliances including an oven, microwave, and refrigerator. Wooden cabinets and open shelves provide storage and decor. A stone floor adds texture, while light fixtures and potted plants contribute to the bright, welcoming ambiance of the space.

Cabin in Jacksonville

Private & Cozy Treetop Cabin in Historic J-vile

Welcome to your private cabin up in the trees, just 3 miles from sought after Historic Jacksonville, Oregon-where award winning restaurants, wineries, and adventures await! Stay for a few days or a couple months and we will take care of you just the same! Set among mature Madrones and Pines with views of the evergreen mountains, you will be using all your senses to discover what Oregon is all about. Lots of fun wildlife! A well behaved pet is welcome with approval. DM for dates not listed.

4.92 out of 5 average rating, 169 reviews

The charming exterior of a vintage guest cottage is highlighted, featuring warm wooden siding and green-framed windows. Soft lighting from hanging bulbs creates a welcoming ambiance, while potted plants and rustic barrels add natural elements to the entrance.

Guesthouse in Ashland

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!

Superhost

A hot tub filled with clear water is positioned on a private deck, offering panoramic views of surrounding mountains and lush forest. Sunlight reflects off the water's surface, enhancing the tranquil setting, with a glimpse of a river in the distance.

Guest suite in Jacksonville

4.87 out of 5 average rating, 183 reviews

The Birdhouse Retreat| Views & Hot Tub

Take it easy at this unique and tranquil getaway. Immerse yourself with the sound of the forest gazing at the Applegate valley and lavender farms below. Walk around in over 10 acres of forest and enjoy a forest bath and sounds of the river below. Minutes from renowned Applegate Valley wineries and Applegate lake. Snow capped mountains in view most of the year. This space has a private bedroom and bathroom with a separate entrance. For the chilly nights, enjoy a cozy fireplace and a movie.

4.96 out of 5 average rating, 122 reviews

A spacious outdoor area features a crystal-clear swimming pool adjacent to a stone hot tub. Surrounding greenery and colorful flowers enhance the serene setting. Seating options are available nearby, with steps leading elegantly from the house to the poolside.

Home in Ashland

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Guesthouse in Lithia Park

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 out of 5 average rating, 210 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.

4.98 out of 5 average rating, 288 reviews

A spacious bedroom features a colorful quilted bedspread with floral patterns. Large glass doors open to a private balcony, providing views of the surrounding mountains. A ceiling fan is mounted above, and a flat-screen television is positioned on the wall opposite the bed.

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.

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.

4.93 out of 5 average rating, 1,113 reviews

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.

4.86 out of 5 average rating, 116 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.

Guesthouse in Ashland

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!

4.95 out of 5 average rating, 489 reviews

A small studio cottage is presented with a light green exterior and a sloped roof. Two red chairs are positioned on a concrete deck, surrounded by planters with greenery. Tall evergreen trees frame the background against a bright blue sky with scattered clouds.

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!

4.97 out of 5 average rating, 295 reviews

A cozy log house features a red metal roof and is surrounded by tall trees and lush greenery. The structure showcases a covered porch area and a spacious, welcoming outdoor space. Sunlight filters through the trees, enhancing the serene forest setting.

Home in Ashland

Secluded mountain retreat, 10m. to Ashland, by PCT

Beautiful hand built log house nestled in the Cascade mountains of Southern Oregon. 15 minutes to Ashland, 20 minutes to Mt. Ashland Ski Area, and a three minute walk to Pacific Crest Trail. This home is a cozy, quiet getaway: surrounded by a 38 acre old forest w/ endless mountains and trails at your doorstep. Features include glassed in sun room (sleep under the stars), fully equipped kitchen, large covered deck, seasonal wood-fired sauna, swimming pond and walking trails.

Popular amenities for Ashland pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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.

4.98 out of 5 average rating, 154 reviews

Charming One

A bright bedroom features a spacious bed adorned with neutral bedding. A wooden desk and lamp are positioned nearby, with framed photographs decorating the walls. Natural light filters through a window draped with sheer curtains, while a small potted plant adds a touch of greenery.

4.96 out of 5 average rating, 188 reviews

Clean, comfy, pet friendly & fully stocked

4.96 out of 5 average rating, 122 reviews

A comfortable living room is furnished with two sofas and an armchair, arranged around a wooden coffee table. Soft pillows complement the seating. A lamp stands beside a wall, providing light, while artwork adorns the walls, adding a serene touch to the space.

Home in Phoenix

Phoenix Rising (Sleeps 10)

4.99 out of 5 average rating, 207 reviews

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

Hygge Hideaway. A home for rest and adventure

A cozy room is presented with a queen bed draped in a light green coverlet. A wooden desk and chair are positioned near a window adorned with cream curtains, while an area rug adds warmth to the hardwood floor. Decorative accents include wall art and a classic wooden dresser.

4.91 out of 5 average rating, 198 reviews

Historic Upstairs Apartment

A cozy living area is characterized by a comfortable sofa and two patterned chairs surrounding a wooden coffee table. A dining table for two is positioned nearby. Natural light enters from a window, while an air conditioning unit and wall-mounted television contribute to a functional space.

4.93 out of 5 average rating, 150 reviews

Cute, pet friendly Guest House

4.99 out of 5 average rating, 307 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

4.97 out of 5 average rating, 275 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

Pet-friendly home rentals with a pool

Superhost

A comfortable living area features a large brown leather sofa and matching loveseat, complemented by a wooden coffee table. Natural light enters through expansive windows framed by curtains, providing views of the surrounding greenery. A ceiling fan and wooden accent pieces enhance the cozy ambiance.

Guest suite in Gold Hill

4.84 out of 5 average rating, 111 reviews

Amazing Rogue River frontage/1-BR guest house/pool

4.96 out of 5 average rating, 324 reviews

A shared fire pit is surrounded by outdoor seating, providing a cozy gathering space. Warm light from the interior of the cabin and string lights create an inviting ambiance, while tall trees frame the backdrop, enhancing the peaceful setting.

Cabin in Grants Pass

Tiny Cabin in the Woods | Hot Tub & Alpaca Rescue

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, 460 reviews

Sweet Vintage Cottage steps from Rogue River

4.9 out of 5 average rating, 50 reviews

A charming two-story home features light blue siding and a welcoming front porch. Lush greenery surrounds the property, along with blooming pink flowers and neatly trimmed bushes. An inviting blue door with an oval window serves as the focal point, framed by large windows on either side.

Home in Ashland

Indulgent Retreat: 3 King Suites, Pool & Hot Tub

4.93 out of 5 average rating, 188 reviews

The exterior of the house is illuminated by string lights, casting a warm glow in the evening. The pathway is lined with greenery, leading to a seating area with a fire pit, surrounded by trees and a scenic hillside view beyond.

Apartment in Medford

Broken Chair Ranch

4.95 out of 5 average rating, 890 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

4.81 out of 5 average rating, 112 reviews

A spiral staircase leads to an upper level, crafted with wooden steps and a sleek black railing. The open floor plan reveals a modern kitchen with bar seating, large windows providing natural light, and views of the surrounding nature.

Home in Trail

Oregon Riverfront Oasis •Pool •Hot Tub •Sleeps 10+

5 out of 5 average rating, 14 reviews

The Sunflower Cabin features a red exterior adorned with green vines, nestled among trees. A gravel pathway leads to the entrance, surrounded by natural landscaping. The cabin's roof is metal, adding to its rustic charm while harmonizing with the serene, wooded environment.

Guesthouse in Talent

Sunflower

Private, pet-friendly home rentals

4.85 out of 5 average rating, 124 reviews

A modern cabin with wooden siding is illuminated at dusk. The structure features large glass windows, offering views of the forest. A spacious deck with railing extends from the cabin, surrounded by trees and natural foliage, creating a serene atmosphere.

Cabin in Grants Pass

Rogue River Glamping

4.96 out of 5 average rating, 107 reviews

A wooden exterior is showcased, featuring a white door with four glass panes. Lush green vines and plants are arranged alongside the entrance, enhancing the natural charm of the space. A welcome mat is positioned in front of the door on a concrete pathway.

Farm stay in Ashland

Mountain House property studio apartment

4.9 out of 5 average rating, 99 reviews

Guesthouse in Medford

W/D, FULL Kitchen, Downtown walking , Parking

4.94 out of 5 average rating, 143 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

The exterior of the charming home features a light grey facade with white trim, complemented by a welcoming porch. Wooden planters are mounted under two windows, and a neatly landscaped path leads to the front door, framed by seasonal foliage.

4.88 out of 5 average rating, 389 reviews

Southern Oregon Gem (EV Charger)

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.

4.98 out of 5 average rating, 255 reviews

Sand Creek Cottage

A spacious bed is neatly made with decorative pillows and a patterned throw. A colorful wall art featuring a whale is displayed above the bed. Light enters the room through glass patio doors, revealing a small outdoor seating area with chairs.

4.95 out of 5 average rating, 110 reviews

Delightful suite in a peaceful neighborhood!

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.