Guesthouse holiday rentals in Ashland

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Top-rated Guesthouses in Ashland

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse in El Sobrante

4.98 out of 5 average rating, 112 reviews

Hidden Gem in the Valley

The guest house is nestled in the May Valley, where amazing views of the hills awaits from the bedroom windows and private backyard patio, surrounded by variety of fruit trees. It's central location makes it ideal as home base to explore the Bay Area's top attractions, from San Francisco, Napa Valley to Sausalito among others. Target, Safeway, Lucky, Riley's, Trader Joe's, Sprouts, Foodmaxx are all within minutes of driving distance, you'll have the varieties you need for a comfortable stay.

Top Guest favourite

Guesthouse in Oakland

4.97 out of 5 average rating, 239 reviews

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated 82F May 1st-Oct. 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Top Guest favourite

Guesthouse in Danville

4.88 out of 5 average rating, 276 reviews

Welcoming Private Guesthouse

Private entrance with direct access to Iron Horse Trail. Freestanding unit with bedroom, living room, kitchenette (not full kitchen) and bathroom. Walkable to Downtown Danville. Visiting family in Alamo, Danville, Lafayette, San Ramon or WC- inquire about the Family or CPC Events discounts. Set on 1/2 acre estate, walking distance to village. Coffee shops, bars, restaurants and family friendly pubs, Hot Summer Nights car show and Farmers Market. SF, Wine Country and Silicon Valley ~ 1 hour

Top Guest favourite

Guesthouse in Walnut Creek

4.97 out of 5 average rating, 166 reviews

Gorgeous Guest House with a Farmhouse Flair

Gorgeous new guest house tucked away from it all and yet close to Downtown Walnut Creek! Walnut Creek is truly a gem of a city right out side San Francisco with cutting-edge restaurants and retail shopping. Staying in our guest house will give you a taste of the country in a organic setting of the yard. This open floor plan is bright and airy, spacious kitchen with large peninsula view for eating and socializing. Beautiful front porch perfect for warm summer nights, with views of the hills.

Guest favourite

Guesthouse in San Rafael

4.89 out of 5 average rating, 221 reviews

Beautiful Guesthouse with direct view of the Bay

Beautiful furnished guesthouse located in east San Rafael, with a spectacular view of the water and Richmond Bridge. Located only a few minutes away from San Rafael downtown, where there is an abundance of coffee shops, restaurants, and bars. It is also walking distance from Trader Joe’s and Whole Foods. Guesthouse comes equipped with a queen sized bed (Saatva luxury mattress), pull out sofa, and a kitchenette. Beautiful oasis. 40 mins from wine country and 25 mins from SF.

Guest favourite

Guesthouse in San Rafael

4.97 out of 5 average rating, 378 reviews

Coleman Cottage - Hillside Paradise

Open, airy, private guesthouse in the San Rafael Hills of Marin County. Recently remodeled and completely refurnished with new appliances this beautiful setting affords all of the amenities and comforts for a home away from home. Located 20 minutes from San Francisco and 30 minutes from wine country with nearby hiking and biking trails, you will experience the best of the Bay Area. ** We are in compliance with all Covid-19 protocols and policies as set forth by Marin County. **

Guest favourite

Guesthouse in Redwood City

4.95 out of 5 average rating, 437 reviews

🌼Modern guesthouse w private patio and ♨️ hot tub

New and modern guesthouse, built in 2018, 20 min walk to downtown Redwood City. The kitchen comes fully equipped with high-end appliances, quartz countertops, Keurig coffee maker, and an eat-in island. In the living room, enjoy the 55" 4K TV with Bose sound on a sectional sofa that doubles as a pull-out bed. Rest well on a premium cal king size bed and enjoy a relaxing dip in the hot tub on your tranquil backyard patio. Unit has washer/dryer, heat/AC, and ensuite bath.

Guest favourite

Guesthouse in Oakland

4.91 out of 5 average rating, 338 reviews

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.

Superhost

Guesthouse in Alameda

4.86 out of 5 average rating, 123 reviews

Pet-Friendly Guest House with Private Patio

Tranquil 1 bedroom 1 bathroom guest house. The space is calm and serene nestled in a lush urban garden surrounded by trees. Prime location where guests are walking distance from neighborhood cafes, and Downtown Alameda which has an assortment of excellent restaurants, bars, and shopping. Amenities include: Queen Bed with pillow top 42 inch Smart TV with Disney Plus & Hulu Private Wifi And More... Early check-in starting at 12pm an additional $35.

Guest favourite

Guesthouse in Woodside

4.93 out of 5 average rating, 145 reviews

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

Top Guest favourite

Guesthouse in Woodside

4.99 out of 5 average rating, 538 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Guest favourite

Guesthouse in Berkeley Hills

4.87 out of 5 average rating, 200 reviews

Berkeley Hills Bay cottage w/ loft work space

Experience the blend of privacy and convenience in our fully gated, detached cottage. Nestled in the lush, exclusive Berkeley Hills, this escape is your ideal haven for work, study, and relaxation. A designated quiet residentail space -no gatherings, please. Enhance your productivity in a dedicated loft space, complete with fiber optic high-speed WI-FI that extends to the charming patio area.