Holiday houses in Ashland

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Ashland

  • Total holiday rentals

    Explore 100 holiday rentals in Ashland

  • Verified guest reviews

    Over 3,580 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Ashland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ashland rentals

  • 4.7 Average rating

    Ashland stays receive an average rating of 4.7 out of 5 from guests

Top-rated holiday rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious living area features a combination of seating arrangements, including an elegant wooden bench and a long dining table surrounded by upholstered chairs. Bright natural light enters through large sliding doors, complemented by soft drapes. A painting is displayed on the wall, adding character.
Home in San Leandro
4.9 out of 5 average rating, 108 reviews

San Francisco TOP Vacation Home 旧金山最舒适民宿

Welcome to San Francisco!!! Top rated vacation home located in SAFE and quiet area. Close to SF major attractions, UC Berkeley, Oakland Stadium! Newly remodeled entire house with 4 bedrooms and 2 full bathrooms. Enjoy outdoor gas BBQ grill. Extra large family room. All bedrooms are furnished. Allows up to 14 guests. Your stay will be so comfortable, and it feels like home! Central Heating and AC. Office setup & fast WiFi broadband. Washer & Dryer Available. Bienvenido...Welcome...歡迎全世界華人游客入住!!!

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
4.95 out of 5 average rating, 153 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!

Superhost
A cozy dining and resting area features a sleek glass coffee table atop light wood flooring. A gray futon is positioned near a wall-mounted flat-screen TV, while a compact stainless steel fridge and air fryer sit on a black stand. Vertical blinds allow filtered light to enter.
Guesthouse in San Lorenzo
4.87 out of 5 average rating, 110 reviews

15B - Cozy & Comfortable 1B1B Back Unit

This is a newly remodeled back unit of a single family house. It has a Queen bedroom, a nice dining/resting room with smart TV (no local channels), air fryer, fridge, coffee basic utensils, and free laundry. - 3 mins drive to Bayfair BART station - 15 mins drive to Oakland Airport - 25-min drive to San Francisco - Min away to Hwy 880, 238 & 580 -Mins walk to Walmart, Starbucks, Grocery outlet, restaurants and many more. Our place is perfect for 1-2 guests who want a private relaxing stay.

Superhost
A welcoming entryway features a plush gray bench and vibrant wall art, including a vintage soda advertisement and a large STOP sign. Light wood flooring leads into a cozy living area, which is visible through an open doorway, creating an inviting atmosphere.
Home in Castro Valley
4.82 out of 5 average rating, 91 reviews

Handcrafted Retreat | Stunning Views 2Br with AC

Escape to this uniquely designed retreat with stunning city & mountain views. Thoughtfully curated with handcrafted details, this cozy stay offers a mini kitchen with a coffee maker, microwave, and kettle, plus a spacious deck for relaxation. Enjoy fast WiFi, Smart TV, and plush bedding in a space filled with artistic charm. Perfect for creatives, remote workers, or a peaceful getaway. Located near local cafés, artisan shops, and nature trails. Book now for a unique, design-forward escape!

Guest favourite
A modern living area features a dark sectional sofa and a glass-topped coffee table. A small dining table with two chairs is located beside a window. Decorative wall art is displayed above the furniture, and a portable air conditioner is positioned in a corner.
Guest suite in San Lorenzo
4.95 out of 5 average rating, 213 reviews

570 - Cozy & Comfortable 1B1B guesthouse w/parking

This is a newly remodeled adjacent unit of a single family house. It has a Queen bedroom, a nice living room with portable AC, a futon, smart TV, fridge, airfryer, microwave, coffee, basic utensils - 3 mins drive to Bayfair BART station - 15 mins drive to Oakland Airport - 25-min drive to San Francisco - Min away to Hwy 880, 238 & 580 -Mins walk to Walmart, Starbucks, Grocery outlet, restaurants and many more. Our place is perfect for 1-2 guests who want a private relaxing stay.

Guest favourite
The exterior of the charming single-unit showcases a light-colored facade with a sloping roof. A white picket fence frames the entrance, where a small garden of pink roses and greenery adds a touch of color. The sky above is bright with wispy clouds.
Apartment in San Leandro
4.84 out of 5 average rating, 117 reviews

2BR |King Bed |Exclusive Parking|Walk to Grocery

***UPDATE: Just finished a full kitchen renovation May 2026, fresh cabinets, new countertops. We think you'll love it! Welcome to our lovely 2BR, 1BA unit in San Leandro. Enjoy a cozy King-size bed in one room and a comfortable Queen-size bed in the other. Minutes from Oakland Airport, BART, supermarkets, and shopping plaza. Relax in the bright living room and make use of the fully equipped kitchen. Perfect for a family or friends’ getaway. Book now for a memorable stay!

Top Guest favourite
Guest suite in San Lorenzo
4.97 out of 5 average rating, 389 reviews

Tiny Casita/Studio | Near Oakland, SF & SJ

Welcome to our <b>Cozy Casita Studio </b>✨ Peaceful stay for up to two guests with private entrance, queen bed, kitchenette with mini fridge and microwave, and full bathroom with standing shower. Compact private studio conversion. 🐾 <b>Pet-friendly</b>! The casita is fully private with its own entrance but attached to our home, so occasional household sounds may be heard. Conveniently located minutes from San Francisco, Oakland Airport, and 30 minutes from San Jose Airport.

Guest favourite
A cozy studio interior features a spacious bed with a light-colored blanket and a soft grey tufted bench. A smart TV is mounted on the wall, and a kitchenette area with essential appliances is visible in the background. Natural light filters through blinds enhancing the warm ambiance.
Guesthouse in Hayward
4.81 out of 5 average rating, 143 reviews

Adorable Private Garden Studio

Centrally located, cozy, fully furnished studio with all of the amenities needed for a relaxing stay! Just bring your luggage! Conveniently located in a Hayward garden oasis near freeways leading to San Francisco, San Jose, and Palo Alto. You will be pleasantly surprised once you enter the property by how well hidden this gem is away from the busy bustle of Hayward. Enjoy your morning coffee in the sunny courtyard or perhaps share a glass of wine by the fire-pit in the evening.

Superhost
Home in Castro Valley
4.81 out of 5 average rating, 70 reviews

The Red Edit w/AC | Scarlet Retreat, Deck & Views

Welcome to The Red Edit — a bold and stylish 2BR, 1BA retreat in Castro Valley. Designed with vibrant scarlet tones and modern touches, this cozy home is perfect for families, couples, or creatives. Enjoy a spacious living room, a fully equipped kitchen, and a private deck with outdoor seating and sweeping city views. Whether you're exploring nearby parks and cafes or simply relaxing in our unique space, this unforgettable stay invites you to recharge and make lasting memories.

Superhost
Home in San Lorenzo
4.81 out of 5 average rating, 31 reviews

Spacious 3BR w/ Large Backyard | Near SF & OAK

Spacious 3-bedroom, 2-bath home with a large private backyard and patio, perfect for families and groups. Enjoy a fully equipped kitchen, comfortable living spaces, fast WiFi, AC, and in-unit washer & dryer for added convenience. Includes one dedicated off-street parking spot plus free street parking. Located just 0.9 miles from Bayfair Mall and BART, with easy access to SF, Oakland, OAK airport, and Silicon Valley. A comfortable, well-located home base for your Bay Area stay.

Guest favourite
A spacious living area is highlighted by a modern sectional sofa facing a central coffee table. Large windows allow natural light, framed by decorative plants. A dining table is set off to the side, enhancing the open layout of the room.
Townhouse in Castro Valley
4.94 out of 5 average rating, 137 reviews

Spacious 3BR Home Near San Francisco

Spacious 3-Bedroom Home Near San Francisco Welcome to our comfortable 3-bedroom, 2-bath home in Castro Valley, ideal for families visits, business travelers, tech professionals, traveling nurses and extended stays. This 1,300 sq ft home features central A/C, fast WiFi, a fully equipped kitchen and comfortable beds. Located in a quiet, safe neighborhood. We maintain a peaceful, respectful environment. Parties, events, loud music, smoking, and drug use are not permitted.

Superhost
Guest suite in Hayward
4.93 out of 5 average rating, 265 reviews

Private Guest Suites | Fast Wifi & Parking

Enjoy a comfortable and private guest suite perfect for business travelers, couples, or anyone visiting the Bay Area. The space is clean, quiet, and thoughtfully set up so you can relax, work, or explore with ease. The suite features a private entrance, cozy sleeping area, comfortable living space, and convenient amenities to make your stay feel like home. Whether you’re here for work or a quick getaway, you’ll have everything you need for a smooth and restful stay.

Popular amenities for Ashland holiday rentals

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Ashland?

    Ashland has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in guesthouse rentals in Ashland?

    Experience the best of Ashland with our guesthouse rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Ashland?

    Yes! Work meets play with ease at over 50 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Ashland have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ashland have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Ashland have wifi?

    Absolutely! We offer over 10 guesthouse rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Ashland have free parking?

    Absolutely! We offer over 10 guesthouse rentals with free parking in Ashland. Enjoy a tailored experience with all the comforts you desire.