
Holiday rentals in Ashland
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Top-rated holiday rentals in Ashland
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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.

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!

Private and serene studio with full kitchen
Lovely studio is light and bright with a vaulted ceiling and sky light, and the property is in a country setting. It is close to hiking trails, Redwood Canyon Golf Course, Lake Chabot, shopping and restaurants, Bart, and easy access to the freeway. The outside view is a meadow, hiking trail, and rolling hills. The studio has a full kitchen so if you decide to cook, we have all the tools you’d need for you to prepare a meal. We’d love to host you for stays of two days up to 28 days at a time.

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.

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.

East Bay Cozy Cottage
Your lovely cottage is ready and perfectly located to explore the Bay Area or catch a flight in or out. This peaceful space has a plush, comfy queen size bed and a fold down sofa-futon (best utilized for a child or teenager). There is a well-stocked kitchenette. BBQ grill too. We are conveniently located near the two main highways linking all East Bay destinations. Oakland's Oracle Arena (15 min), Jack London Sqr (25 min), San Francisco-downtown (40 min), Lake Chabot (10 min)

Guesthouse Garden Retreat
Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

Hike-in Bay Views Cabin w HotTub
Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

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.

Peaceful Retreat w/ Views + Gated Parking
This romantic getaway is perched on a sunny ridge among redwoods, fruit trees, and a garden, with sweeping views of the bay and spectacular sunsets, behind a secure gate with door-side parking in a safe, quiet residential neighborhood. Situated on 1/2 acre away from busy streets, but with easy access to all the Bay Area has to offer. This slice of heaven will delight you with thoughtful and luxurious touches.

“The white house”
Deep sanitized after each guest. Simple and beautiful !All brand new duplex,from concrete foundation to furniture. Central A/C .About 1300 square feet, 3 bedrooms 2 full bathrooms. Nice ,new fresh smell throughout the home. We like to keep the place nice and clean, WE DONT ALLOW ANY PARTY OR GATHERING , loud music ,smoking or drug use on our property . Great neighborhood.

Cozy Bungalow near Bart to SF, SJ, & Hwy 238 & 580
Welcome to this charming Bungalow 2-bedroom 1-bath single family home that offers you a fully equipped nice stay with comfort in the neighborhood of Castro Valley, conveniently commute to many central locations, and minutes to Bart station to S.F., S.J., Oakland, and other destinations. (Station map and location details available inside the house).
Popular amenities for Ashland holiday rentals
Stay near Ashland's top sights
Other great holiday rentals in Ashland

Tiny Casita - Close to Oakland/SF/SJ

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

Bungalow Guest House

Modern & Cozy Cottage

Modern Hillside Retreat

Crest retreat home

Cozy house with spectacular views of the Bay Area

Charming Backyard Guest House with Koi Pond
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $130 SGD | $131 SGD | $137 SGD | $130 SGD | $142 SGD | $146 SGD | $154 SGD | $156 SGD | $144 SGD | $141 SGD | $135 SGD | $137 SGD |
| Avg. temp | 11°C | 12°C | 13°C | 15°C | 16°C | 18°C | 19°C | 20°C | 20°C | 18°C | 13°C | 11°C |
Frequently Asked Questions
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.
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.
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 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 house rentals in Ashland have free parking?
Absolutely! We offer over 40 house rentals with free parking in Ashland. Enjoy a tailored experience with all the comforts you desire.
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 townhouse rentals in Ashland?
Experience the best of Ashland with our townhouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Guesthouse Rentals in Ashland?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Ashland

Total holiday rentals
Explore 100 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 3,260 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Ashland holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ashland rentals

4.6 Average rating
Ashland stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
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- Stanford University
- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Golden Gate Bridge
- California’S Great America
- Alcatraz Island
- Baker Beach
- Twin Peaks
- SAP Center
- Mission Dolores Park
- Montara State Beach
- Henry Cowell Redwoods State Park
- Bolinas Beach
- Pier 39
- Six Flags Discovery Kingdom
- Palace of Fine Arts'`
- Davenport Beach
- Pescadero State Beach
- Winchester Mystery House
- Rodeo Beach
- Painted Ladies
- San Francisco Zoo
- Santa Maria Beach




