House holiday rentals in Ashland

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Top-rated house rentals in Ashland

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Guest favourite
The bedroom features a spacious bed with a textured blanket draped across it, and soft ambient lighting enhancing the surroundings. Decorative wall hangings add interest, while a mirror and a hanging rack are present for convenience.
Home in Fairview
4.93 out of 5 average rating, 151 reviews

Emerald stay. Timeless. Relaxing

Follow the yellow bricked entry to a timeless, relaxing stay. A mix of modern indirect lighting, the warmth of indoor plants, and classic yarn art. The Emerald Stay has a spacious living room that opens out to an equally spacious private deck with fabulous sunset bay views, and a shaded relaxation space, under large oak trees. Enjoy your private entrance, deck, and zero sightlines to any neighbor windows. The Emerald Stay is a tranquil escape in the East Bay. This is a soundproof divided house.

Top Guest favourite
The exterior of a spacious home is set within the Oakland Hills, featuring a paved driveway leading to an entrance. Lush greenery and natural stone landscaping flank the sides, while a gentle slope showcases the house’s elevated position.
Home in Oakland
4.99 out of 5 average rating, 159 reviews

5 Bedroom home with bay views for large groups

Spanish-style home in the Oakland hills , a quiet neighborhood Spacious, open layout with fantastic views of the San Francisco Bay Area. Great location: Close to Montclair village and quick access to San Francisco. Half-mile walk to the best open space parks in the east bay: Joaquin Miller Park! Features one acre of attractive gardens, patios, and a large deck with bay views. Great for family reunions, get-togethers or larger families. Plenty of parking, 4 cars+, in huge private driveway

Top Guest favourite
A modern kitchen features high-end stainless steel appliances and a spacious island with slick bar stool seating. The well-lit area is complemented by contemporary pendant lights. Double french doors open to a backyard, enhancing the connection between indoor and outdoor living.
Home in Castro Valley
4.96 out of 5 average rating, 137 reviews

The Blue Door Retreat

This hotel-like home has been professionally renovated and designed to maximize the comfort, convenience and enjoyment of your stay. The kitchen has a huge WOW factor w/ stainless high-end appliances, fully stocked, ideal for cooking, entertaining, or baking. Indoor/outdoor living w/ double french doors that both open up to the beautiful backyard space complete with patio furniture, BBQ and firetable, ideal for enjoying our amazing CA weather. Smart TV's in every room for those Netflix nights!

Guest favourite
The living area is defined by a cozy couch with decorative pillows, positioned across from a wall-mounted TV. Natural light filters through a skylight and window, illuminating the room adorned with soft curtains. A small coffee table rests on a neutral area rug, contributing to a relaxed atmosphere.
Home in Oakland
4.97 out of 5 average rating, 235 reviews

The not so tiny, tiny house (with private laundry)

This tiny house is a 525 sqft home sitting offset from our main home. It has everything from a fully stocked kitchen to a laundry room inside this cozy home. Pots/pans, dishes and even a crock pot and waffle maker stock the kitchen. You will have a private fenced in front area with a seating area and artificial grass. We have built this home to welcome you as our friends and keep you comfortable. The home is located in a dog friendly neighborhood. * we do decorate for major US holidays

Top Guest favourite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.94 out of 5 average rating, 437 reviews

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Top Guest favourite
An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.
Home in Mill Valley
4.99 out of 5 average rating, 125 reviews

Two Creeks Treehouse

Looking for a healthy dose of tranquility and adventure at your doorstep? Over 100 steps from the road below, this 'treehouse' is perched above it all and horizontally oriented on a steep lot between two creeks. The all glass façade creates dramatic views of the redwoods, Mt. Tam and across downtown Mill Valley to Blithedale Ridge. Anchored to granite the house sits on handmade stone walls from rock harvested on the property during construction in the 1960s. Truly a one of a kind stay.

Guest favourite
The exterior of the home features a two-story design with a stucco finish and a tiled roof. A neatly landscaped front yard is framed by shrubs and small trees, while a spacious driveway leads to the two-car garage.
Home in Hayward
4.89 out of 5 average rating, 137 reviews

Hayward Hills | 4BR • Private Court • Fireplace

Escape to this 4BR/3BA Hayward Hills retreat in a quiet neighborhood with a spacious interior and backyard patio. Centrally located home in the heart of the SF Bay area, this home is a short distance to airports, hiking trails, and attractions. If you are looking for something private, relaxing, and centrally located, this is the home you're looking for. Our home is an ideal retreat for families or groups looking for a peaceful escape. We look forward to hosting you!

Guest favourite
A private balcony features comfortable seating arrangements with a cushioned daybed and stylish rattan chairs. A large umbrella provides shade, and a small table holds a bottle and glass. Lush greenery surrounds the space, complementing the serene outdoor setting.
Home in Oakland
4.89 out of 5 average rating, 331 reviews

Travelers Paradise l Free Parking

Welcome to my Bright, Happy Home. You will feel at peace the moment you walk in and see the view! Every room is full of light. Studies show that access to natural light indoors heals the body and mind! Benefits of Natural light: + Increases happiness + Provides vitamin d + Sparks creativity 》10 min to downtown Oakland/Oakland Airport 》30 min by car to San Francisco without traffic 》1.5 hr to Napa wine valley without traffic *NO SMOKING ON or IN THE PROPERTY*

Guest favourite
Home in Oakland
4.95 out of 5 average rating, 156 reviews

Urban Renaissance

Enjoy comfort and privacy in this spacious retreat featuring a 3-bedroom, 2-bath main house and a separate 2-bedroom, 1- bath guest house with private entrances. Perfect for families, groups, or multigenerational stays. Includes central heating/AC, Wi-Fi, and a sunny outdoor space. Travel together, relax apart! The backyard offers a private oasis with outdoor furniture and a BBQ grill—perfect for dining al fresco or enjoying warm evenings under the stars.

Top Guest favourite
The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.
Home in Montara
4.98 out of 5 average rating, 404 reviews

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

Top Guest favourite
A bright living area features a comfortable gray sectional sofa and a stylish armchair, surrounded by natural light from large windows. A decorative electric fireplace is positioned below a wall-mounted TV, with two patterned chairs and a small end table completing the space.
Home in Castro Valley
4.98 out of 5 average rating, 209 reviews

Cheerful 2-bedroom near San Francisco &FW580/238AC

Welcome to Tom & Melissa's a cheerful 2-bedroom 1-bath in a single family house, It is a spacious 1016 sq feet house. Centrally located in the East Bay, and very close to freeway 580 and 238! You're within 30 minutes of San Francisco or 40 minutes of San Jose. Enjoy this spacious residential home with a large private patio, two separate bedrooms, a bright and comfortable living space, and a kitchen, making it a great place for family or couples.

Top Guest favourite
A spacious outdoor seating area features a sectional couch with soft cushions surrounding a firepit, all set against a backdrop of sweeping views of the San Francisco Bay. Lush greenery and modern fencing frame the relaxing space.
Home in Oakland
4.97 out of 5 average rating, 102 reviews

Newly remodeled hilltop home with stunning views

Enjoy breath-taking views of San Francisco and the bay from a fully remodeled, casually luxurious hilltop home. A peaceful retreat in the heart of the Bay Area just minutes from great restaurants, live music and endless park trails. Lounge by the firepit or the fireplace; whip up something in the gourmet kitchen or outdoor grill, or hike serene wooded trails to your heart's content.

Popular amenities for Ashland house rentals

Quick stats about house rentals in Ashland

  • Total holiday rentals

    Explore 40 holiday rentals in Ashland

  • Verified guest reviews

    Over 1,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Ashland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ashland rentals

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