Guesthouse vacation rentals in Ashland

Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!

Tucked between pine, oak, & redwood trees is a 4 year old, high end cottage nestled with amazing views of the mountains. Peaceful, upscale gated, property. 1 mile to large regional parks for hiking, mountain biking & horse stables. Nature at its best! Pool heated to 82F 4/1-10-31. 16 miles to San Francisco, 5-10 minutes to many restaurants. Jacuzzi & barrel sauna, grill. Large patio, pool /new deck (6500 sq foot outdoor oasis shared with main house small family of 4). Own spot in driveway.

Family · Value · Bathroom

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.

Location · Family · Accuracy

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 Again, you get both! Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

Family · Value · Parks

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.

Value · Family · Hospitality

15min walk to Bart/New remodel/Private entrance

Private access to the entire guest suite. Front door parking for 1 vehicle. Nice, quiet, peaceful, children friendly, convenient and centrally-located place. The unit is brand new remodel, washer and dryer in the unit! Walking distance to public transportation, including BART train, within 15mins to OAk, within 30mins to SFO. Major car rental is nearby. - queen size bed - twin size bed - computer desk - independent Central AC/ Heating - Full kitchen & eating utensils - Fast wifi

Family · Value · Wifi

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.

Family · Value · Check-in

Adorable Private Garden Studio

Centrally located, cozy, fully furnished studio with all of the amenities needed for a relaxing stay! Just bring your luggage! Conveniently located in a Hayward garden oasis near freeways leading to San Francisco, San Jose, and Palo Alto. You will be pleasantly surprised once you enter the property by how well hidden this gem is away from the busy bustle of Hayward. Enjoy your morning coffee in the sunny courtyard or perhaps share a glass of wine by the fire-pit in the evening.

Location · Family · Walkability

Peaceful Retreat w/ Views + Gated Parking

This romantic retreat is perched on a sunny ridge with sweeping views of the bay, surrounding hills, and spectacular sunsets. Farm vibes with California natives, fruit trees, redwoods, and outdoor space to enjoy. 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.

Location · Family · Comfort

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

Family · Location · Heating

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.

Value · Family · Breakfast

Cozy Private Entrance Studio

Keep it simple at this peaceful and centrally-located space. Whether you’re visiting for a few days or a month this unit/location has everything you’ll need. Close to wildlife/great trails/lookouts, 10 minutes from downtown Oakland, and just 30 minutes from San Francisco. Perks include open parking, easy access to the freeway, and a quiet neighborhood.

Value · Family · Hospitality

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.

Family · Location · Air conditioning