Holiday rentals with outdoor seating in Ashland

4.97 out of 5 average rating, 492 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.

4.93 out of 5 average rating, 101 reviews

A spacious bedroom features a large bed adorned with neutral-toned bedding and decorative pillows. A stylish seating area with a daybed rests opposite a window, providing natural light. Soft wood flooring complements the modern design, while minimalistic artwork and a plant add subtle touches.

Apartment in Ashland

Ashland Zen Den

Brand new remodeled and designed downstairs basement apartment on Main St. in Ashland. This modern space is clean and peaceful. Each bedroom is equipped with high end mattresses, linens, TV, and bath robes. There are plenty of books to read and board games to entertain. Enjoy a short walk to downtown where you will find Lithia park, restaurants, cafes, and shopping! 25 min. drive to mt Ashland and world class MTB. Walking distance to Shakespeare festival. Plenty of beautiful wineries near by!

4.94 out of 5 average rating, 452 reviews

A cozy living area features a leather sofa and a patterned armchair, complemented by a wooden coffee table. A flat-screen TV is mounted on the wall, while large windows allow natural light to fill the space, highlighting the warm wood paneling.

Cottage in Ashland

Charming very well appointed cottage !

The Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 1 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If comfort what you are looking for, the cottage will meet all your needs.

4.96 out of 5 average rating, 129 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, 237 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.

5 out of 5 average rating, 161 reviews

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

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.

4.88 out of 5 average rating, 133 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!

4.93 out of 5 average rating, 772 reviews

A cozy seating area features a spacious brown sofa adorned with purple accent pillows. Natural light pours in through large windows, highlighting the wooden paneling throughout the room. Framed art pieces hang above the couch, complementing the warm environment.

Farm stay in Ashland

Kelly’s Farm 4 miles to Ashland

Nestled on the border of the Shakespeare hamlet of Ashland, Oregon, is Kelly’s farm. Only four miles away from Ashland. Kelly’s farm has horses, goats, chickens, gardens, fruit and nut trees with views of Mt. Ashland’s seven-thousand feet high profile in its front and bucolic rolling hills in its back. Bring your dog! You have access to a large fenced in yard right from your private entrance and deck. ***Unfortunately we are not set up for children under 4 or kitty cats.

4.96 out of 5 average rating, 243 reviews

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

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. NOTE: AFTER JULY 1ST, 2026, COYOTE MOON WILL NO LONGER BE AVAILABLE FOR BOOKING AS AN AIRBNB.

4.91 out of 5 average rating, 137 reviews

The exterior of the Serendipity House features a light-colored facade with a welcoming porch shaded by trees. Garden areas with stone pathways are present, enhancing the home's approachable charm. Large windows allow natural light to illuminate the inviting entrance.

Home in Ashland

Charming house two blocks from downtown Ashland

The Serendipity House is a comfortably stylish escape in the heart of Ashland. Our newly remodeled home has all the comforts you will need. Cozy beds for sleeping late, a full kitchen with a complimentary coffee bar, a living room for socializing with family and friends, and all the privacy of having the entire property to yourselves. Restaurants, shopping, and theater begin two blocks away. This is the perfect house for your unforgettable Ashland experience.

4.97 out of 5 average rating, 110 reviews

A cozy living area features a blue sectional sofa and an accent chair, with a flat-screen television mounted on the wall. A sliding barn door leads to the kitchen area, which showcases modern appliances. Natural light filters through the window, enhancing the spaciousness.

Cottage in Ashland

Sweet Breeze Bungalow

Charming Alley bungalow in the historic railroad district. Walk score of 93. Immerse yourself in the heart of Ashland. 5 min. walk to downtown, an easy 8 min. walk to Shakespeare & Cabaret Theaters. Walk to pubs, restaurants, coffee shops, spa's, markets, movie theater, Lithia Park, Japanese garden and trailheads all within 5-12 mins. Nice bike ride to wineries 15 min away, or a 30 min. drive to Mt. Ashland for skiing, hiking, biking and more adventures.

Superhost

A modern tiny home is positioned against a backdrop of rolling hills. A large wooden deck extends from the structure, offering a space for outdoor enjoyment. Natural light highlights the home's sleek exterior, which combines metal and wood elements.

Tiny home in Ashland

4.82 out of 5 average rating, 244 reviews

Ashland tiny home with view and barrel sauna

Vaulted 8.5x20 craftsman tiny home built in 2023. Large wrap around deck overlooking the hills of Ashland. Stunning space to reset, relax and enjoy. Five minutes to downtown ashland. Great bird watching. Fall asleep to the sound of crickets on a comfortable queen bed in the upstairs loft. BBQ out on the deck, with all new amenities. Mini split heat pump and shared barrel sauna. We hope you enjoy the space as much as we do.

Popular amenities for Ashland outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.99 out of 5 average rating, 143 reviews

Home in Grants Pass

New Barndo: Stunning Rogue River access!

4.96 out of 5 average rating, 198 reviews

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.

Home in Medford

Clean, comfy, pet friendly & fully stocked

4.99 out of 5 average rating, 215 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

4.94 out of 5 average rating, 167 reviews

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.

Home in Medford

Cute, pet friendly Guest House

4.99 out of 5 average rating, 318 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

Spa Like Stay at the Britt Bungalow in J’Ville

4.97 out of 5 average rating, 276 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, 150 reviews

Home in Grants Pass

Stylish home with private access to Rogue River!

4.79 out of 5 average rating, 117 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+

Apartment rentals with outdoor seating

4.88 out of 5 average rating, 269 reviews

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

Winner 2024 Best of Ashland! Our Carriage House

4.9 out of 5 average rating, 105 reviews

Apartment in Medford

W/D, FULL Kitchen, Downtown walking , Parking

4.93 out of 5 average rating, 189 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

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.

4.95 out of 5 average rating, 899 reviews

Peace on the Rogue river Studio

A fully equipped kitchen features white cabinetry, a stove, and ample counter space. A round table and chairs are positioned in the foreground. Natural light enters through a window, highlighting the organized layout and functional design of the space.

4.82 out of 5 average rating, 225 reviews

Great location to I-5 and city! King bed!

A wooden outdoor seating area is positioned on a concrete patio, featuring two chairs and a loveseat with white cushions. A table sits in the center, surrounded by blooming purple flowers and green vegetation. Large glass doors lead into the interior space.

4.95 out of 5 average rating, 232 reviews

1940s Vintage apartment steps from the Rogue River

A stylish sitting area features a leather couch adorned with patterned cushions. In front, a circular coffee table is topped with a decorative plant and a book. A wall hanging with 'GRANTS PASS OREGON' adds a local touch to the bright space.

4.94 out of 5 average rating, 175 reviews

Brand New Stylish MCM Studio

4.83 out of 5 average rating, 18 reviews

The exterior of a large contemporary castle estate is shown, featuring multiple levels and a driveway leading to it. Surrounding the building, green grass and blossoming trees indicate the presence of gardens, while classical stone sculptures and a fountain are visible in the foreground.

Apartment in Ashland

Chateau Herbe ~ Juliet Carriage House studio

Condo rentals with outdoor seating

A spacious living area is showcased, featuring a comfortable sofa and armchair arrangement. A large screen is mounted on the wall, displaying a serene forest scene. Soft light filters through large windows, and a modern fireplace adds a touch of warmth to the space.

4.98 out of 5 average rating, 44 reviews

Plaza North Suite 203 Windsor

A spacious living area is furnished with a gray sectional sofa and two light armchairs, arranged around a round coffee table. Large windows provide natural light, highlighting the neutral decor and textured rug. A dining area with a wooden table and upholstered chairs is visible in the background.

5 out of 5 average rating, 59 reviews

Plaza North Suite 201 Alexander

The entryway is marked by the number '202' on the door, welcoming guests into a bright living space. A comfortable sofa is positioned beside a small side table, accompanied by decorative vases. Natural light fills the room through large windows, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 35 reviews

Plaza North Suite 202 Sonoma

The open living area features a mix of contemporary furniture, including a light-colored sofa and two armchairs. Large windows allow natural light to fill the space, complemented by greenery from potted plants. A dining area is visible in the background, enhancing the welcoming atmosphere.