
Holiday houses in Ashland
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Top-rated holiday rentals in Ashland
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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!

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.

★COZY & Unique Guest Suite★ (Wifi, Netflix & MORE)
Located in the “Heart of the Bay” is our cozy & private guest suite (SUITE A). Just a 5 minute drive to downtown Hayward & BART, 20 minutes from Oakland International Airport and 35 minutes from SFO. You'll have ONE dedicated parking space on our driveway for your vehicle & SEPARATE entrance. Complimentary coffee, tea, and snacks provided. Perfect for couples or professionals coming to CA for an extended stay. Enjoy the Bay Area's beauty and excitement from your stay in the middle of it all!

Handcrafted Hillside Retreat | Stunning Views 2Br
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!

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.

The Red Edit | Scarlet Heaven Retreat |Deck & View
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.

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)

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.

Cozy In-Law Suite Near Lake Chabot | 40 Min to SF
🌟 Cozy & Modern In-Law Suite in Castro Valley! Escape to our private in-law suite, nestled in a serene neighborhood near Lake Chabot 🌳. Perfect for solo travelers or couples, this unit offers a clean, modern ambiance with natural light streaming through. Enjoy a kitchenette for your meals and a private entrance for complete independence. Plus, you're just a mile from scenic trails, hiking, and kayaking at Lake Chabot!"

Charming Backyard Guest House with Koi Pond
Charming and cozy, this cottage has beautiful back yard with koi pond and bridge is ideal for both weekend getaways as well as longer stays. Centrally located in the bay area, clean, modern accommodation. Only 3 miles from Bart, 10 miles from OAK and 30 miles from SFO. Relax in your own room in a completely updated home.

A Home Away From Home
You can just grab your bag and come to stay in my place just feel like home. A cozy, relax and private place in a blind alley with well-stocked amenities. It’s located near 3 busy HWY 880,238 & 580. And also close to the Bayfair BART station, SF International airport, SF Downtown, Oakland airport, & Coliseum.
Popular amenities for Ashland holiday rentals
Other great holiday rentals in Ashland

Room in Hayward Townhouse

Luxury Master Sui. Scenic Views

c4# Newly renovated private villa with cozy and elegant rooms, quiet and safe, beautiful scenery.

Experience a tranquil stay in the Oakland Hills.

Stay with Michael

Wonderful Place to stay.

Heart of the Bay Area

Business-friendly Room in Hayward w/Fast Wifi (DA)
When is the best time to visit Ashland?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | $153 AUD | $155 AUD | $161 AUD | $153 AUD | $167 AUD | $172 AUD | $163 AUD | $161 AUD | $163 AUD | $166 AUD | $160 AUD | $161 AUD |
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 |
Quick stats about holiday rentals in Ashland
Total rentals
100 properties
Nightly prices starting at
$15 AUD before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Northern California Holiday rentals
- San Francisco Bay Area Holiday rentals
- San Francisco Holiday rentals
- Gold Country Holiday rentals
- Central California Holiday rentals
- San Francisco Peninsula Holiday rentals
- San Jose Holiday rentals
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- Santa Barbara Holiday rentals
- San Joaquin River Holiday rentals
- Wine Country Holiday rentals
- Golden Gate Park
- Stanford University
- Oracle Park
- Muir Woods National Monument
- Twin Peaks
- Golden Gate Bridge
- SAP Center
- Bolinas Beach
- Mission Dolores Park
- Montara State Beach
- Henry Cowell Redwoods State Park
- Davenport Beach
- Pier 39
- Pescadero State Beach
- Six Flags Discovery Kingdom
- Palace of Fine Arts'`
- California’S Great America
- Rodeo Beach
- Painted Ladies
- Winchester Mystery House
- San Francisco Zoo
- Bonny Doon Beach
- Santa Maria Beach
- Half Moon Bay State Beach