Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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Top guest favorite
The kitchen is equipped with modern appliances, including a microwave and coffee maker. Light-colored cabinetry complements the marble countertop. Shelves display decorative items and there is a cozy coffee bar. Natural light enters through a window, enhancing the inviting atmosphere in the space.
Guest suite in San Leandro
4.99 out of 5 average rating, 103 reviews

Modern & Cozy Cottage

Welcome to The Modern Comfort Cottage ! It is located in a safe and friendly neighborhood in San Leandro, just a 5-minute drive to Downtown and the BART station, 15minutes to the Oakland International Airport, 30 minutes to San Francisco. Enjoy modern conveniences including an in-unit washer and dryer for your convenience. Parking is easy with provided parking spaces, and street parking is also available. Stay in this newly renovated cottage for a comfortable living experience. Enjoy and unwind!

Guest favorite
The bedroom features a spacious bed with a textured blanket draped across it, and soft ambient lighting enhancing the surroundings. Decorative wall hangings add interest, while a mirror and a hanging rack are present for convenience.
Home in Hayward
4.95 out of 5 average rating, 127 reviews

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.

Top guest favorite
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
4.96 out of 5 average rating, 110 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 favorite
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.
Guesthouse in Castro Valley
5 out of 5 average rating, 110 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 favorite
A cozy dining and resting area features a sleek glass coffee table atop light wood flooring. A gray futon is positioned near a wall-mounted flat-screen TV, while a compact stainless steel fridge and air fryer sit on a black stand. Vertical blinds allow filtered light to enter.
Guesthouse in San Lorenzo
4.94 out of 5 average rating, 100 reviews

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.

Top guest favorite
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, 192 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 favorite
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, 257 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 favorite
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, 348 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 favorite
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
4.9 out of 5 average rating, 155 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.

Top guest favorite
A cozy studio space features a spacious bed with layered bedding. Soft light filters through patterned curtains near a window. A comfortable seating area is nearby with a textured throw, and an electric fireplace adds warmth. A flatscreen TV is mounted on the wall, adjacent to the bathroom.
Guesthouse in Castro Valley
4.99 out of 5 average rating, 171 reviews

Peaceful Retreat w/ Views + Gated Parking

This romantic getaway is perched on a sunny ridge with sweeping views of the bay, surrounding hills, and spectacular sunsets. Farm vibes with California natives, fruit trees and redwoods. No shared walls, behind our family home inside a secure gate with door-side parking. Super quiet in a safe, residential neighborhood. Convenient to everything in the Bay. Perfect home base for visiting family, work trips and extended stays.

Top guest favorite
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, 234 reviews

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

Newly renovated in-law SUITE B, located in the “Heart of the Bay”. Just a 5 minute drive to downtown Hayward & BART, 20 minutes from Oakland International Airport & 30 minutes from SFO. In-N- Out, SPROUTS, Raising Canes & Starbucks NOW OPEN just 4 min away!! Our guest suite is 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!

Top guest favorite
A spacious living room is presented, featuring a black sofa, two ancient chairs, and a round coffee table. A decorative lamp stands beside the seating area, with light oak flooring and a soft area rug enhancing the inviting environment. Natural light filters through the windows.
Bungalow in Castro Valley
4.96 out of 5 average rating, 217 reviews

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 vacation rentals

When is the best time to visit Ashland?

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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 vacation rentals in Ashland

  • Total vacation rentals

    Explore 100 vacation rentals in Ashland

  • Nightly prices starting at

    Ashland vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

  • Verified guest reviews

    Over 3,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Ashland vacation rentals include wi-fi 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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