Holiday rentals 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 living space showcases a comfortable gray sofa with decorative pillows. A wall-mounted TV is positioned across from the seating area, with a dining table and bar stools visible in the open kitchen. Light wood flooring complements the bright, airy atmosphere.
Guest suite in Hayward
5 out of 5 average rating, 242 reviews

★UNIQUE STAY in the middle of the BAY★ Wifi+MORE!

Comfortable in-law suite located in the “Heart of the Bay.” Just a 5-minute drive to downtown Hayward and BART, 25 min. from OAK Airport, and 35 min. from SFO Airport. In-N-Out, Sprouts, Raising Cane’s, Starbucks and much more are conveniently located just 4 minutes away. Our space is ideal for couples, travelers, and guests looking for a well-located home base. Enjoy easy access to nearby cities, dining, transportation, and experience the Bay Area’s energy and diversity from a central location.

Top guest favourite
A private patio features two chairs with cushions positioned around a small table. Lush greenery surrounds the space, complemented by vibrant flowers in a blue planter. A red awning provides shade, adding a cozy touch to the outdoor area.
Guest suite in Oakmore
4.97 out of 5 average rating, 1,045 reviews

Sunset Spa Suite w/private patio, views & parking

This private suite is a slice of heaven in a woodland setting! Accessed via a flight of garden stairs, it has a private entry, dedicated street parking, a private patio, luxurious large bath with a walk-in shower for 2, large jacuzzi tub for 2, heated floors, A.C., mini fridge, toaster oven, & microwave! The bedroom features a queen-sized bed, table for two, large screen smart TV, and strong fiber optic WIFI signal. Located in a beautiful neighborhood with wonderful hikes just outside the door.

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
4.95 out of 5 average rating, 129 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
A modern building with a green roof is nestled in a lush landscape, surrounded by trees. Scenic views of rolling hills and the bay are visible in the background, offering a serene and natural atmosphere. The driveway leads up to the structure, enhancing accessibility.
Bungalow in Sequoyah
4.95 out of 5 average rating, 101 reviews

Modern 2 bedroom with stunning bay views

Kick back and relax in this calm, stylish space. The Oakland Hills are filled with amazing hiking, this location is great for day trips to Napa (35 miles), San Francisco (11 miles) or Carmel (120 m). Centrally located for work or play. This open concept 2 bedroom is a peaceful break away. Given the open concept design - there is not a lot of privacy between bedrooms, just a big bookcase room divider b/w the rooms. There are a few sitting area's outside and a green roof too! And EV charging.

Top guest favourite
A patio area is visible near the entrance of the studio, featuring a small table and blue chairs. Potted plants line the pathway, leading to the main entrance. Sunlight filters through the surrounding trees, creating a serene outdoor space.
Guest house in Castro Valley
5 out of 5 average rating, 124 reviews

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.

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, 199 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.

Top 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.
Guest house in San Leandro
4.95 out of 5 average rating, 263 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)

Guest favourite
A spacious living area is highlighted by a large window allowing natural light to fill the room. A cozy seating arrangement includes a sofa and armchairs surrounding a coffee table. Features include a fireplace, a smart TV, and decorative plants enhancing the layout.
Holiday home in Castro Valley
4.91 out of 5 average rating, 119 reviews

King Suite, 5 Queen Spacious Modern Home

Welcome to our thoughtfully remodeled, modern, comfortable 4 bedroom home! This home provides the perfect balance of peaceful relaxation with access to everything the Bay has to offer. * One level, accessible. * Large bedrooms with all Queens and King size beds. * New kitchen, bathrooms, appliances, TV, and furnitures. * Office setup and 350Mb speed internet. * A Quiet backyard with a hill view. 5 minutes from 580/880/BART public transit 15 minutes to Oakland Airport

Top 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, 128 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.

Guest favourite
Guest suite in Cherryland
4.94 out of 5 average rating, 224 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.

Top 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
4.94 out of 5 average rating, 375 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.
Guest house in San Lorenzo
4.89 out of 5 average rating, 168 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

Popular amenities for Ashland holiday rentals

Frequently Asked Questions

  • Are there family-friendly house rentals in Ashland?

    Ashland has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Ashland with our apartment rentals, starting at about $10 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 house rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 10 house rentals for guests traveling with pets.

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

    Yes! Work meets play with ease at over 10 guesthouse 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 30 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.

Quick stats about holiday rentals in Ashland

  • Total holiday rentals

    Explore 90 holiday rentals in Ashland

  • Nightly prices starting at

    Ashland holiday rentals start at € 9 per night before taxes and fees

  • Verified guest reviews

    Over 3,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 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

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