Holiday rentals with outdoor seating in Ashland

4.98 out of 5 average rating, 737 reviews

Guest house in Medford

Orchard Home Cottage *Private• Cozy• Peaceful*

*NO PETS* Enjoy Southern Oregon by staying in our peaceful bright cottage. Perfect for those who want a quiet getaway close to all the Rogue Valley has to offer. It is situated toward the rear of our property w/private parking and its own fenced patio. We are located 4 miles from Jacksonville where you can hear the sounds of the Britt Festival. Ashland, home of Oregon's Shakespeare Festival is 20 minutes away. Lakes, hiking trails, and rivers are all around for those looking for adventure.

4.97 out of 5 average rating, 493 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.

A comfortable living area features a light gray sofa adorned with decorative pillows. A flat-screen television is mounted on the wall in front, while a potted plant adds a touch of greenery. Natural light streams in through large windows with blinds, complementing the warm wood flooring.

4.99 out of 5 average rating, 156 reviews

The Cutie Little Loft

The Cutie Little Loft is a clean, stylish and centrally located new build. A comfortable bed, a full kitchen with brand new appliances, and extra special little touches, will make your stay easy and enjoyable. Whether your main destination is Medford, or perhaps you plan to visit nearby cities like historic Jacksonville or Ashland, the CLL is a great point of access for all. Numerous restaurants, hiking trails and wineries are nearby allowing an eventful trip to the beautiful Southern Oregon.

4.93 out of 5 average rating, 102 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.

Flat 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, 454 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.

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.

4.96 out of 5 average rating, 130 reviews

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!

Guest house 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, 240 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.

4.99 out of 5 average rating, 165 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.

Guest house 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, 137 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.

Guest house 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.

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.

4.96 out of 5 average rating, 243 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. NOTE: AFTER JULY 1ST, 2026, COYOTE MOON WILL NO LONGER BE AVAILABLE FOR BOOKING AS AN AIRBNB.

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.

4.91 out of 5 average rating, 138 reviews

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.

Popular amenities for outdoor seating rentals in Ashland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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, 199 reviews

Clean, comfy, pet friendly & fully stocked

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.

4.94 out of 5 average rating, 170 reviews

Cute, pet friendly Guest House

4.97 out of 5 average rating, 277 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!

4.97 out of 5 average rating, 196 reviews

A cozy lounge area is accented by two comfortable chairs and a blue sofa. Large windows fill the space with natural light, framed by greenery outside. A wooden table centers the room, complemented by a textured area rug and decorative artwork on the walls.

Home in Grants Pass

Cozy Riverside Retreat, Dog-Friendly w/Hot Tub

A bright bedroom features a spacious bed adorned with a neutral-toned blanket. Two woven stools are positioned at the foot of the bed, complemented by bedside tables with lamps. A desk is situated in the corner near a large window, enhancing the room's soft, natural light.

4.98 out of 5 average rating, 155 reviews

Cute Boho w Patio, W/D, Parking (No Chores!)

5 out of 5 average rating, 247 reviews

A spacious living area features a light-colored couch paired with a glass coffee table adorned with a floral arrangement. Natural light enters through large windows with sheer curtains, illuminating vintage furnishings and a chandelier hanging from the ceiling.

Home in Jacksonville

Unwind at a Luxury Cottage in Jacksonville's Historic Core

The front porch is showcased with wooden decking, leading to an entrance adorned with potted plants and colorful hanging baskets. A welcoming sign is mounted on the blue exterior wall, complemented by rustic furniture, enhancing the inviting appearance of the home.

4.95 out of 5 average rating, 106 reviews

Cozy Ashland Getaway

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.

Flat in Ashland

Winner 2024 Best of Ashland! Our Carriage House

Superhost

Flat in Medford

4.87 out of 5 average rating, 106 reviews

W/D, FULL Kitchen, Downtown walking , Parking

4.93 out of 5 average rating, 190 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.

Flat 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, 226 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

4.96 out of 5 average rating, 54 reviews

A comfortable living area is shown, featuring a large couch with decorative cushions and a soft throw blanket. A simple coffee table rests in front, adorned with a snack platter. Natural light enters through a window, which overlooks a garden and fenced outdoor space.

Flat in Medford

The Loft

Apartment 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.