Guesthouse holiday rentals in Ashland

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Top-rated Guesthouses in Ashland

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Top Guest favourite

Guesthouse in Dublin

5 out of 5 average rating, 148 reviews

Private In-Law unit in Dublin, CA

Private in-law unit is located behind the main house in a quiet neighborhood in Dublin, CA. Close to BART for an easy commute to San Francisco and near the Iron Horse trail for a morning or evening run. Along with a private entry, one bedroom and a fully equipped kitchen this unit has a sleeper sofa and could accommodate up to 3 guests. Perfect alternative to a hotel if you're travelling to the Bay Area for business or coming to visit family. NO PETS PLEASE. No children under 12 years old.

Top Guest favourite

Guesthouse in Eastmont Hills

4.99 out of 5 average rating, 151 reviews

Serene foothills Garden Suite, private parking +EV

Have the entire Bay Area at your fingertips... & right outside your window! This private studio tucked into the Oakland Foothills is the perfect base for adventures. A 9min drive & you can be on the train into San Francisco. Coliseum & redwoods are minutes away, as are many other attractions*. You’ll be welcomed home to a comfy California King bed & a serene garden view. Enjoy coffee/tea as you settle in at the table, & our high speed wifi has you covered. Have an EV? Charge Level 2 overnight!

Top Guest favourite

Guesthouse in San Carlos

4.99 out of 5 average rating, 734 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Top Guest favourite

Guesthouse in Oakland

4.97 out of 5 average rating, 252 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)

Guest favourite

Guesthouse in Millsmont

4.79 out of 5 average rating, 942 reviews

The Purple Door, Private Sanctuary, Epic View

Private guesthouse located in the Oakland Hills with stunning views of the bay. We recognize the importance of privacy, this guesthouse will allow you to have everything you need all while never having to be bothered. The sunset views can be taken in from your bed or the deck. There is a bus stop about 150 yards away if you need, the airport is about a 7 minute ride away, rail (BART) is about 5 minutes and the house is near a freeway for quick access to everywhere in the Bay Area.

Guest favourite

Guesthouse in San Leandro

4.95 out of 5 average rating, 242 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

Guesthouse in Redwood Heights

4.93 out of 5 average rating, 238 reviews

Eco-Cottage Sanctuary in Garden Oasis

Our popular cottage is like a retreat experience in the city! The cottage is an enchanting oasis nestled in the back and quiet from street noise. You will sleep comfortably on our new mattress topper! Our urban farm and garden offers a unique heartwarming experience-with lush gardens, frogs, chickens and 3 young goats! The cottage is perfect for guests looking for a comfortable space to relax after a busy day. Come and enjoy our beautiful and relaxing eco-friendly cottage!

Guest favourite

Guesthouse in Walnut Creek

4.96 out of 5 average rating, 113 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Guest favourite

Guesthouse in Oakland

4.91 out of 5 average rating, 351 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.

Guest favourite

Guesthouse in San Lorenzo

4.89 out of 5 average rating, 141 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.

Guest favourite

Guesthouse in Piedmont Pines

4.97 out of 5 average rating, 280 reviews

Bright Modern Secluded Oakland Hills Retreat

Bright, secluded, cozy and modern detached studio in Montclair / Oakland Hills. Just across the bay from San Francisco. Queen bed, full bath and open kitchen w/ appliances + dining bar w/ bay vista views. Hike/bike trails 5 min. away. Your oasis is up the hill past trees, the occasional deer and a few turns through a friendly neighborhood. Car is essential to reach your private getaway!

Top Guest favourite

Guesthouse in San Leandro

4.93 out of 5 average rating, 137 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.