House holiday rentals in Ashland

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Top-rated house rentals in Ashland

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Guest favourite
The sunroom features expansive glass windows that offer a panoramic view of the city and hills at sunset. A cozy seating area with a light blanket and soft cushions is present, providing a relaxing space to enjoy the scenic landscape.
Home in Daly City
4.96 out of 5 average rating, 254 reviews

SF Amazing View & SUNroom: Spacious Private 1 bdrm

👋 Welcome to our spacious, clean, private getaway studio on Southern Hill in Daly City. Escape the hustle and bustle of the city. Enjoy a stunning view of day/night in clear days ☀️ - Easy street parking - Great Summit Loop Trail at San Bruno Mountain (6-min🚘) - Cow Palace Arena (8-min🚘) - H Mart grocery mall (10-min🚘) - 9.2 miles to SFO (17-min🚘) - 6.7 miles to Civic Center(>30-min🚘 w/ traffic or 20-min🚘 w/o traffic) - 11 miles to Fisherman's Wharf(>35-min🚘 w/ traffic or 23-min🚘 w/o traffic)

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 Woodminster
4.99 out of 5 average rating, 158 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, 136 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!

Top Guest favourite
The bright yellow exterior of the home features a decorative arched entrance, a large window, and a blue garage door. Red steps lead to the front door, with potted plants arranged along the pathway. Clear blue skies provide a vibrant backdrop.
Home in Alameda
4.95 out of 5 average rating, 203 reviews

Beautiful Spanish Bungalow

Welcome to a delightful 2 bedroom, relaxed and comfortable home. You have easy access to San Francisco by Ferry. You'll have a short walk to many restaurants and pubs. It's equipped with high speed fiber internet with AppleTV, including HBO and other paid services. This home has comfortable beds with plenty of pillows, plus a fully equipped kitchen.  It's in a quiet, friendly neighborhood, so you can enjoy a safe, calm place, with lots to do all around, including a 10 minute walk to the beach.

Guest favourite
A secluded hot tub is surrounded by lush greenery and towering redwoods, providing a tranquil retreat. Stone tiles create a pathway leading to the tub, which is nestled amongst ferns and other foliage, enhancing the natural setting.
Home in Mill Valley
4.94 out of 5 average rating, 157 reviews

Redwood Treehouse, Downtown Mill Valley

Majestic, secluded home in the redwoods yet just a few minutes walk to all the amenities of downtown Mill Valley. The home truly feels like a tree house amongst the giant redwoods of Mill Valley. Hike the world famous Dipsea Trail, enjoy the beauty of Old Mill Park, or simply stay at the house and soak in the natural hot tub surrounded by Redwoods. This place is truly special! Please note, access to the house requires a climb up roughly 200 stairs, if an issue, this is NOT the house for you.

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, 124 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.

Top Guest favourite
The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.
Home in San Carlos
4.96 out of 5 average rating, 306 reviews

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain).

Top Guest favourite
A sunlit dining area is framed by large windows that provide a clear view of the ocean and sunset. A small round table is set with two black chairs, and a woven basket sits at the center, while a soft rug covers the floor.
Home in Moss Beach
4.95 out of 5 average rating, 138 reviews

Oceanfront Oasis, Sunsets & Crashing Waves

The Bluffs Oceanfront Oasis awaits you. Our beautifully appointed home sits right on the cliff boasting crashing waves and endless sunsets. Start your day in the zen room for a bit of yoga and meditation or take a leisurely walk on the beach trail right out the back gate. After dining out or in, end your evening with something special while seated at the firepit over looking the Pacific. Come for a romantic getaway, a weekend of golf or a family fun filled vacation.

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, 401 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, 208 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.

Guest favourite
A cozy living area is arranged with a dark sectional sofa adorned with patterned pillows and a soft throw blanket. A circular coffee table holds a potted plant and decorative items. Natural light filters through white shuttered windows, illuminating the warm, neutral tones of the space.
Home in Alamo
4.83 out of 5 average rating, 115 reviews

Large West Alamo 1 Bedroom In-Law Unit

This in-law unit is the perfect place for anyone visiting in the Alamo, Danville, Walnut Creek and San Ramon Valley areas. Just 22 miles east of San Francisco, 40 miles from Napa, located on the west side of Alamo with easy access to Hwy 680, this large 1 bedroom unit has a separate entrance and is walking distance to hiking trails in Las Trampas regional park and the Iron Horse Trail. Lovely location, quiet and peaceful.

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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