Holiday rentals with outdoor seating in Ashland

4.97 out of 5 average rating, 494 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, 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.

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!

4.98 out of 5 average rating, 236 reviews

A spacious bedroom features a large tufted bed topped with an assortment of decorative pillows. A stylish bench is positioned at the foot of the bed, and a ceiling fan is installed above. Natural light is provided by a nearby window, framed by elegant curtains.

Townhouse in Medford

Light & Spacious 2 Bedroom 2 1/2 Bath

Newer constructed townhouse located at the end of a quite dead end road. The open floor plan offers warmth and comfort, perfect for your business or pleasure trip. Large master W/fireplace-additional second bedroom upstairs. 2 1/2 baths to accommodate everyone. Located within a couple minutes off I5, 12 mins to the airport and minutes to anywhere in Medford. Walking distance to South Medford High school and a short drive to Medford's major rec parks. 5 Step Cleaning. Welcome and Sweet Dreams!

4.94 out of 5 average rating, 456 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.

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, 245 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, 167 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.

4.98 out of 5 average rating, 326 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.

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.

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!

4.96 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, 143 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, 114 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.

4.97 out of 5 average rating, 109 reviews

Home in Talent

Clean and Cozy Historic Home near Ashland

Bedroom 1 is set up with a full size bed, with all-cotton sheets. Mattress is medium firm. Bedroom 2 has a daybed with soft mattress. Bathroom is a few steps away. Ventilating windows, ceiling fan and individual mini-split with a/c or heat in bedroom. Radiant heat and ceiling fan in living room. Easy walk to restaurants, parks, library, bus line, groceries. I live nearby so am available if needed but you will have the house all to yourself!

Popular amenities for Ashland outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.99 out of 5 average rating, 148 reviews

Home in Grants Pass

New Barndo: Stunning Rogue River access!

4.99 out of 5 average rating, 217 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, 173 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

4.97 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, 151 reviews

Home in Grants Pass

Stylish home with private access to Rogue River!

4.97 out of 5 average rating, 221 reviews

A colorful garden welcomes visitors to the cottage, filled with vibrant flowers and lush greenery. A mix of pink, orange, and white blooms create a lively scene, complemented by well-maintained pathways. Two entrances to the cottage are visible, framed by the flourishing landscape.

Home in Medford

the Downtown Mint

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

4.95 out of 5 average rating, 106 reviews

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.

Home in Ashland

Cozy Ashland Getaway

Apartment rentals with outdoor seating

4.88 out of 5 average rating, 271 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

The Carriage House, Winner 2025 Best of Ashland!

Superhost

Apartment in Medford

4.87 out of 5 average rating, 108 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.

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, 902 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!

4.9 out of 5 average rating, 48 reviews

An inviting outdoor patio area features a wooden deck shaded by a pergola. Comfortable lounge chairs with floral patterns are arranged for relaxation. The separate entrance door, painted in a warm orange hue, provides access to the suite, framed by large windows that enhance natural light.

Apartment in Lithia Park

Cowslip's Rosebud Garden Suite, peaceful, central

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

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, 47 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.