Holiday houses in Ashland

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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 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

4.98 out of 5 average rating, 100 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

An airy living space features a light-coloured sofa and a small dining table with two chairs. A coffee and tea station stands on a black cabinet. Natural light enters through the front door, complemented by indoor plants and framed wall art. A doorway leads to the bathroom.

Guest suite in Hayward

4.98 out of 5 average rating, 166 reviews

★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!

Guest favourite

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

4.97 out of 5 average rating, 35 reviews

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!

Top 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

4.96 out of 5 average rating, 186 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

A stylish living room features a large sectional sofa adorned with cushions and a modern coffee table. Large windows allow natural light to fill the space, offering sweeping views. Decorative plants and unique lighting complement the vibrant decor, enhancing the overall welcoming ambiance.

Home in Castro Valley

4.9 out of 5 average rating, 20 reviews

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.

Guest favourite

A cozy sleeping area features a plush bed adorned with a patterned quilt, flanked by two bedside tables with lamps. Decorative wall art depicts trees, enhancing the calming atmosphere, while a throw pillow adds a touch of motivation.

Guesthouse in San Leandro

4.95 out of 5 average rating, 252 reviews

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)

Top Guest favourite

A modern studio features a stylish futon nestled near a small wooden table, suitable for work or dining. A compact fridge and amenities are included in the space. Light streams in through glass doors, leading to a shared outdoor area, enhancing the room's bright and open feel.

Guesthouse in San Leandro

4.91 out of 5 average rating, 34 reviews

Cozy & Comfy studio w/Free Laundry

Welcome to your relaxing retreat! This inviting private studio offers a blend of comfort and convenience, perfect for solo travelers or couples seeking a peaceful getaway. Enjoy a restful sleep on the plush Queen bed, while the Full-size futon provides extra seating or an additional sleeping space. Relax with your favorite shows on the in-room TV, or step outside to unwind in the beautiful, shared backyard—a serene spot to start your morning or wind down in the evening.

Guest favourite

A private hot tub is shown in the foreground, with soft bubbles visible on the surface. In the background, a modern cabin facade features large glass doors reflecting warm sunset hues, framed by a wooden deck with seating.

Cabin in Sheffield

4.93 out of 5 average rating, 333 reviews

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.

Guest favourite

An open living space features dark tiled flooring and natural wood cabinets in the kitchen area. A round dining table with four chairs is positioned near a flat-screen TV. Two bedrooms can be seen through two doors, providing a layout that emphasizes accessibility.

Guesthouse in San Lorenzo

4.89 out of 5 average rating, 149 reviews

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.

Superhost

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

4.83 out of 5 average rating, 80 reviews

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

Welcome to our newly renovated 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, with a nearby BART station, supermarkets, and a 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

A wooden staircase leads upward through a landscaped yard, flanked by palm trees and vibrant vegetation. A stone pathway connects various garden elements. In the background, a koi pond is visible, while a decorative lantern stands at the base of the stairs.

Guesthouse in San Leandro

4.92 out of 5 average rating, 143 reviews

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.

Guest favourite

A cozy sleeping area features a spacious bed with neutral-toned linens and decorative pillows. Two woven bedside lamps provide soft illumination, while a simple wall art piece adds a subtle touch of character. A closet door is positioned to the right.

Tiny home in San Lorenzo

4.92 out of 5 average rating, 184 reviews

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.