
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, Wi-Fi 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.

Cozy Bungalow near Bart to SF, SJ, & Hwy 238 & 580
Welcome to this charming 2-bedroom, 1-bathroom single-family bungalow in Castro Valley. Guests will enjoy exclusive, completely private access to the entire upper level of the main house, which comes fully equipped with all the comforts of home. The property is ideally located for an easy commute to major central destinations and is just minutes from the BART station for seamless travel to S.F., Oakland, and SJ. A transit map and detailed location guides are provided inside for your convenience.
LocationFamilyKitchen

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!!!
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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!
ValueFamilyBathroom

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.
ValueLocationBackyard

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!
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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.
FamilyLocationCheckout

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.
LocationFamilyHospitality

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.
FamilyValueLong stay

16017-Private 2BR Guest Unit near HWY, BART & Mall
This is a detached 2-bedroom 1-bath guest unit with full kitchen and laundry at the back of my house. It has a private entrance which is accessed from our driveway and backyard. It is conveniently located near freeway 580, 880 and 238, and Bay Fair Bart Station. It's also close to Costco, Walmart, Target and many restaurants and shops, as well as everything you need. It is 13-min drive to Oakland Airport, 16 mins to Coliseum, 30 mins to Downtown SF
FamilyValueOutdoor spaces

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.
FamilyValueBarbecue

15A-Modern & Cheerful Comfy 3B2B Front Unit
This is a modern and stylist, newly remodeled 3-bedroom 2-bath front unit of a single family house, with full kitchen and shared free laundry. - 2 mins drive to stores & restaurants (Walmart, Target, Grocery Outlet) - 3 mins drive to Bayfair BART station - 15 mins drive to Oakland Airport - 25-min drive to San Francisco Our place is perfect for a big group of up to 6 guests who want a private relaxing stay and want to explore the Bay Area.
LocationFamilyHospitality

10% off for Weekly Stay Studio in Downtown
Welcome to our cozy and newly remodeled studio in Downtown San Leandro. It offers 1 queen bed & 1 futon sofa bed, modern kitchenette and washer & dryer in unit. Located in downtown San Leandro, offers easy access to bart, I-880 & I-580. Secured gated lot. Our team is dedicated to making your experience memorable, and we are available to assist you with any inquiries.
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Popular amenities for Ashland holiday rentals
Other great holiday rentals in Ashland

Spacious 3BR w/ Large Backyard | Near SF & OAK
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Green Mountain View house 可爱居
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Cozy house with spectacular views of the Bay Area
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Crest retreat home
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The Red Edit w/AC | Scarlet Retreat, Deck & Views
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Beautiful Home Near Silicon Valley
LocationFamilyDecor

Retreat! Huge Private Yard!King Bed!
FamilyLocationLong stay

Handcrafted Retreat | Stunning Views 2Br with AC
LocationFamilyAmenities
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.
Destinations to explore
- San Francisco Holiday rentals
- San Jose Holiday rentals
- Mammoth Lakes Holiday rentals
- Santa Barbara Holiday rentals
- South Lake Tahoe Holiday rentals
- Oakland Holiday rentals
- Sacramento Holiday rentals
- Reno Holiday rentals
- Monterey Holiday rentals
- Fresno Holiday rentals
- Santa Cruz Holiday rentals
- Three Rivers Holiday rentals
- Stanford University
- Golden Gate Park
- Muir Woods National Monument
- Golden Gate Bridge
- Moscone Center
- Oracle Park
- University of California-Berkeley
- Levi's Stadium
- SAP Center
- Henry Cowell Redwoods State Park
- Mission Dolores Park
- Pier 39
- University of California San Francisco
- Six Flags Discovery Kingdom
- California’S Great America
- Oakland Arena
- Bernal Heights
- Palace of Fine Arts
- Big Basin Redwoods State Park
- Rodeo Beach
- Baker Beach
- Montara Beach
- Painted Ladies
- Twin Peaks





