
Guesthouse holiday rentals in Ashland
Find and book unique guesthouse rentals on Airbnb
Quick stats about guesthouse rentals in Ashland

Total holiday rentals
Explore 10 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at $98 AUD per night before taxes and fees

Verified guest reviews
Over 580 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Ashland holiday 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 Guesthouses in Ashland
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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 Cal 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 (J1772)!

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.

Redwood Sanctuary Oakland Hills
Redwood Sanctuary is located in the idyllic Oakland Hills with beautiful vistas, hikes, and parks within a short drive. The home is situated on half an acre of land in the middle of redwood, eucalyptus, and oak trees secluded away from other homes. Montclair village is an 8 minute drive, providing lots of great food and shops. Minutes from Highway 13 and 580. It is a 1 bedroom studio with a queen bed and a pull out sofa bed. It can comfortably accommodate up to 3. We'd love to host your stay!

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.

Detached Cozy Studio w/ private patio garden & BBQ
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.

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

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.

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

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.

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.
Popular amenities for Ashland guesthouses
Family-Friendly guesthouses

Charming Cozy Cottage in Eco-Garden Oasis

Garden getaway near SF

Guesthouse Garden Retreat

Gorgeous Guest House with a Farmhouse Flair

Guest House in the Woods

Traditional Japanese Tea House

Welcoming Private Guesthouse

Private Garden Cottage Belmont Hills*Pool*HotTub*
Guesthouses with a patio

SkyHigh Redwoods Retreat with Bay Views

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

Private suite on 1918 heritage property

Quiet guesthouse near SJ airport with EV charger

Hillside Wellness Retreat | Pool, Gym & A/C

Charming Victorian Retreat | Minutes to SF

Berkeley Bitty House - a little bit of home

Berkeley Bayview Bungalow
Guest house rentals with a washing machine and dryer

The Redwood Retreat

Private In-Law unit in Dublin, CA

Secluded luxury cottage & hot tub

Downtown secluded Retreat on Almond

Lakeshore Cottage

Modern guest house in great location

Downtown Walnut Creek Cottage (The Walnut)

Tropical Garden Cottage +HOT TUB &POOL by Downtown
Destinations to explore
- San Francisco Holiday rentals
- San Jose Holiday rentals
- Mammoth Lakes Holiday rentals
- Santa Barbara Holiday rentals
- South Lake Tahoe Holiday rentals
- Sacramento Holiday rentals
- Oakland Holiday rentals
- Reno Holiday rentals
- Monterey Holiday rentals
- Santa Cruz Holiday rentals
- Fresno Holiday rentals
- Three Rivers Holiday rentals
- Stanford University
- Golden Gate Park
- Muir Woods National Monument
- Moscone Center
- Golden Gate Bridge
- Oracle Park
- University of California-Berkeley
- Levi's Stadium
- SAP Center
- Henry Cowell Redwoods State Park
- Mission Dolores Park
- Pier 39
- Chase Center
- University of California San Francisco
- Six Flags Discovery Kingdom
- California’S Great America
- Oakland Arena
- Palace of Fine Arts
- Rodeo Beach
- Big Basin Redwoods State Park
- Bernal Heights
- Baker Beach
- Montara Beach
- Painted Ladies





