Guesthouse vacation rentals in Ashland

Find and book unique guesthouse rentals on Airbnb

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!

Top-rated guesthouse rentals in Ashland

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious studio is showcased with a large bed and a serene wall mural of trees. Natural light fills the room through sliding glass doors, which lead to the outside garden. A comfortable chair and side table create a cozy seating area.
Guesthouse in Alameda
4.92 out of 5 average rating, 130 reviews

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.

Top guest favorite
An outdoor jacuzzi is positioned beside a sparkling pool, surrounded by a spacious wooden deck. Lush greenery and trees create a natural backdrop, while distant mountain views are visible in the background. A bottle of champagne sits elegantly on the edge of the jacuzzi.
Guesthouse in Oakland
4.96 out of 5 average rating, 302 reviews

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.

Top guest favorite
Guesthouse in Castro Valley
4.99 out of 5 average rating, 133 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.

Superhost
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
4.87 out of 5 average rating, 109 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.

Guest favorite
A private garden space is enclosed by wooden fencing, featuring various plants and greenery. Steps lead down to a lower level, where a darker area includes more foliage. Soft lighting illuminates sections of the garden, enhancing the tranquil atmosphere.
Guesthouse in Oakland
4.8 out of 5 average rating, 1,031 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 favorite
A cozy studio interior features a spacious bed with a light-colored blanket and a soft grey tufted bench. A smart TV is mounted on the wall, and a kitchenette area with essential appliances is visible in the background. Natural light filters through blinds enhancing the warm ambiance.
Guesthouse in Hayward
4.81 out of 5 average rating, 141 reviews

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.

Top guest favorite
A serene outdoor space is presented with two red Adirondack chairs positioned around a white table. A vibrant tree with red foliage serves as a backdrop, surrounded by well-maintained grass and garden features. Bright skies add to the inviting scene.
Guesthouse in Concord
4.98 out of 5 average rating, 195 reviews

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.

Guest favorite
Guesthouse in Walnut Creek
4.96 out of 5 average rating, 137 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 favorite
Guesthouse in Oakland
4.91 out of 5 average rating, 398 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 favorite
Guesthouse in San Lorenzo
4.89 out of 5 average rating, 176 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
Guesthouse in Woodside
4.99 out of 5 average rating, 586 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.

Top guest favorite
A wooden staircase leads up from a lush garden, surrounded by various greenery and bright flowers. A koi pond is visible beneath the staircase, with vibrant orange trees providing a pop of color. Sunlight illuminates the scene, creating a serene outdoor ambiance.
Guesthouse in San Leandro
4.92 out of 5 average rating, 158 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.

Popular amenities for Ashland guesthouse rentals