
Guesthouse vacation rentals in Ashland
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Ashland
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Detached Cozy Studio w/ private patio garden & BBQ
Newly renovated 100 yr old backyard studio in the heart of the Alameda island. Private fenced garden with bbq. 7 mins from Oakland Int. Airport. 20 mins to SF city by ferry. Convenient location to UC Berkeley. Close to BART, beach, parks, local markets and restaurants in walking distance. • Fully-equipped, self contained studio, with cooking basics, microwave, airfrier/oven, induction cooktop, coffee machine, electric water boiler, BBQ, patio. Private entrance. No share ventilation.

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.

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.

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.

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.

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.

Concord Lavender Farm
Come and relax in our calm, stylish guesthouse. You will be surrounded by an urban lavender farm with 300+ plants to enjoy! DISCLAIMER: Our property is operated as a micro home farm, which entails certain risks from plants, animals and equipment, including lavender, agave, fruit trees, honey bees, chickens, rakes, saws, pruning sheers, etc. By agreeing to stay here for any period of time, you acknowledge and agree to the inherent risks that may occur on a small farm property.

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

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.

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 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.

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.
Popular amenities for Ashland guesthouse rentals
Family-friendly guest house rentals

Mill ValleyTreehouse: MtTam Redwood Sauna ReTREEt

Claremont Canyon Retreat

Berkeley Bitty House - a little bit of home

Oakland Jungalow Cabin Studio
Lulu's Place: a safe gated retreat min to Downtown

Private in-law unit cute and cozy

Lush Luxury Villa • Sunny Deck & Private Escape

Modern guest house in great location
Guest house rentals with a patio

Quaint two-bedroom cottage with patio!

Charming Victorian Retreat | Minutes to SF

Very Demure, Very Cozy, 2 bd guest home w/ hot tub

Sunny Cottage in Redwood City

Villeta Pastena - Rockridge guest house w/patio

Near Japantown & SJC ARPT, King Bed, Fast Internet

Cozy Boho Bungalow

SkyHigh Redwoods Retreat with Bay Views
Guest house rentals with a washer and dryer

Gorgeous Guest House with a Farmhouse Flair

Private Garden Studio, fast wifi near Bart

Cozy Alameda Garden Cottage

Cozy Home + Garden in the Hills

Woodsy Silicon Valley Cottage

Rockridge Garden Cottage

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Private/Relaxing New Guest House & Fast Wi-Fi
Quick stats about guesthouse rentals in Ashland

Total vacation rentals
Explore 10 vacation rentals in Ashland

Nightly prices starting at
Ashland vacation rentals start at G$14,637 GYD per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Ashland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ashland rentals

4.8 Average rating
Ashland stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Northern California Vacation rentals
- San Francisco Bay Area Vacation rentals
- San Francisco Vacation rentals
- Gold Country Vacation rentals
- Central California Vacation rentals
- San Francisco Peninsula Vacation rentals
- San Jose Vacation rentals
- Silicon Valley Vacation rentals
- North Coast Vacation rentals
- Santa Barbara Vacation rentals
- San Joaquin River Vacation rentals
- Wine Country Vacation rentals
- Moscone Center
- Stanford University
- Golden Gate Park
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
- SAP Center
- Pier 39
- Henry Cowell Redwoods State Park
- Mission Dolores Park
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Twin Peaks
- Rodeo Beach
- Levi's Stadium
- Palace of Fine Arts
- California’S Great America
- Montara Beach
- Bolinas Beach
- Winchester Mystery House
- Painted Ladies
- University of California San Francisco
- Chase Center
- San Francisco Zoo





