
Guesthouse holiday rentals in Ashland
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Top-rated Guesthouses in Ashland
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Ashland guesthouses
Family-Friendly guesthouses

North Berkeley Hills Tranquil Writer's retreat
Camille’s retreat is a true oasis, where you can escape the hustle and bustle of the day. Even when relaxing inside, you feel as if you are in the middle of the garden thanks to the large and plentiful windows surrounding you. The only sounds we heard were the birds, who were also enjoying garden. Camille is welcoming and kind and has truly created a serene and lovely space fo repose. Thank you for sharing your lovely home with us, Camille.

Simplistic Crocker Suite
Five stars all around. This was my wife and I's second time staying at Mai's place (the first time being one year ago on our honeymoon!). We love SF, and Mai's place is the perfect respite from the city while remaining relatively close to most areas of interest. Mai is so kind and accommodating, and her place surely does feel like home! We look forward to staying here again and again in the future.

Little Cottage on the Hill
We thoroughly enjoyed our stay. We were comfortable, slept well, and loved the private and beautiful surroundings

Traditional Japanese Tea House
Very quiet and peaceful setting for relaxation and reading and writing. Easy walking to a lot of good restaurants and public transport. Rainbow and Zan were easy to communicate with and facilitated an early check in which was helpful. Would stay here again!

Cottage near dwntwn Palo Alto, Stanford, Face-book
This was a perfect place to decompress during a busy work trip. The space is beautiful, and the attached gym is such a nice treat! Everything was exactly as described, clean and lovely. I would definitely stay again!

Sunny studio near UCB
It was a great stay. They have a beautiful property and garden. Berkley is a great walking city. It was fun to explore. This was my 2nd time to Berkeley, and my wife and kid's first. She loved the city. Thanks for a great stay.

Cozy backyard cottage
This apartment has a lovely garden, which makes a stay very special. People should know that the apartment does not provide much space for cooking and clothes, especially for two guests, since it is just a tiny house. Raquel is very supportive, friendly, helps where she can very quickly and is flexible with the check-in and check-out times, which helped us a lot. It also great that a washer and dryer is included.

Mt Carmel Cottage Charmer-Bright, Stylish & Clean
Perfect place for 2 people. Clean, all the amenities we needed, private and quiet.
Guesthouses with a patio

La Casita - a quiet studio, Crocker Amazon area!
Very clean, quiet neighborhood, and had everything we needed! Would be happy to stay again.

Cozy Private 1B1B Cottage near Japantown
The cottage was absolutely beautiful! Very accommodating and very clean and quiet. Arthur was the perfect host! Our only issue was the parking. We were in San Jose for a church conference that took place off of 1st Street near 237. We wouldn't get back to the cottage until after 10 p.m. so had to park a block or so away both nights. But, it won't stop us from returning. We will be back for next year's conference. Thanks again Arthur!

Private garden retreat
When we entered Mary Lee’s backyard where the unit is located, we were instantly pleased with how beautiful and well landscaped it is. The studio is well built, with attention to detail and the use of quality materials. The décor was also pleasant and well thought out. In addition, we were satisfied with the fact that they provide 100% cotton towels and linen for the bed. The kitchen was well stocked with stainless steel cookware and everything we needed. Mary Lee and her husband David were friendly and responsive to all our requests. We would be happy to stay at their place again.

Delightful Hideaway in San Carlos
This spot is very well located, quiet, clean with everything you need. Very comfortable bedding. Very pleasant shaded patio. Marilynn is very friendly and responsive. An example, broken coffee maker changed within the next hour. We had a very good stay in this accommodation. Thanks again!

Berkeley Bitty House - a little bit of home
Eugenia’s place and Eugenia and her husband are fantastic… One of the most comfortable organic cotton beds I’ve ever slept on, the most enchanting, beautiful property, and every appliance state of the art, efficient and intentional with the touch of love. Eugenia brought me teas, and various unconventional items I asked for. And the natural light and airflow were wonderful. And very healing and the most peaceful and healing neighborhood I’ve stayed at in the East Bay. For anyone looking for a healing retreat, Book this place as soon as possible

SkyHigh Redwoods Retreat with Bay Views
My wife and I recently stayed at HiC and Jeff’s charming unit. The thoughtful details made our stay special, with an incredibly comfortable bed for a great night's sleep. All the amenities, local recommendations, and small touches ensured a relaxing getaway. The beautiful outdoor areas among the redwood trees provided a peaceful retreat to unwind. HiC was welcoming and attentive, making our stay exceptional. We would definitely return to this lovely unit and recommend it for anyone seeking a serene escape in nature!

Private and serene studio with full kitchen
We enjoyed our stay at Chris’s studio. The location is perfectly located to all the essentials but far enough off the beaten track to enjoy a peaceful and relaxing stay. We had everything necessary to enjoy home made meals and coffee in the morning. Loved the setting and her garden was gorgeous. Chris was extremely nice and we would highly recommend a stay here.

Pet-Friendly Guest House with Private Patio
Super spot for us! We were in town for a party and the host was great at checking in to make sure we had everything we needed! Lovely Airbnb!
Guest house rentals with a washing machine and dryer

Gorgeous Guest House with a Farmhouse Flair
The quaint little cottage was tucked away in a peaceful neighborhood, nestled right in the backyard of the owner's home. We absolutely loved spending some quality time together! The beds were comfortable! They were nice and firm, just how I like it. The chickens were absolutely adorable, and they were being taken care of so well! We can't recommend this place enough and are already looking forward to our next visit!

Private Garden Studio, fast wifi near Bart
Loved my stay! It was the perfect home base while exploring the Bay Area. Felt super safe—especially as a woman traveling alone—to be behind the main house, a locked gate, and with my own personalized entrance code. The space had everything I needed for a comfortable stay. Would definitely recommend!

Private&Comfy! Everything you need! No shared Area
We've stayed at this location multiple times. It has everything we need i.e comfortable bed, well supplied kitchen (Hope includes coffee, creamer and sugar), bathroom with plenty of towels, hair dryer. shampoo, condiioner and body wash included, laundry facilites, iron and ironing board. All great. The landscaping is so pretty and there is a private patio with comfy furniture for enjoying the CA sunshine. Highly recommend.

Cozy Alameda Garden Cottage
This was the first time we stayed at the Cozy Cottage, and we cannot rate it highly enough! The cottage was immaculate, the bed very comfortable, and the kitchen well stocked. Mary and Steve went above and beyond to make sure we had everything we needed, even providing a very generous snack basket and cold beverages. The location is also perfect. Easy 2 block walk to the main business district with good restaurants and shops, and about a 10 minute walk from the beach. We will definitely return.

Unique tiny house w huge windows & deck, near lake
I absolutely loved staying here, and would recommend this space to anyone who wants a unique and quiet space to stay in a really lovely part of town. It is worth mentioning that this space comes with some well communicated restrictions on sound during certain hours so make sure to read the listing closely before booking.
Lulu's Place: a safe gated retreat min to Downtown
What a great spot!! Totally private and safe, but right by the best park in Oakland. Special bonus that there was kids books!

Private in-law unit cute and cozy
It was very clean and spacious, and we were able to relax completely. Highly recommended!

Tranquil and Charming 1-Bedroom Guest house w/bath
This place was a very cute and peaceful retreat from the daily grind. I only stayed one night but it was everything I needed and expected. Clean and with all the amenities, great stay and I’d stay here again!
Quick stats about guesthouse rentals in Ashland
Total rentals
20 properties
Nightly prices starting at
$84 NZD before taxes and fees
Total number of reviews
780 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Golden Gate Park
- Stanford University
- Oracle Park
- Twin Peaks
- Bolinas Beach
- Davenport Beach
- Montara State Beach
- Pescadero State Beach
- Muir Woods National Monument
- Rodeo Beach
- Mission Dolores Park
- China Beach, San Francisco
- Rockaway Beach
- Bonny Doon Beach
- Black Sands Beach
- Joaquin Miller Park
- Golden Gate Bridge
- Children’S Fairyland
- Limantour Beach
- Pier 39
- SAP Center
- San Gregorio State Beach
- Six Flags Discovery Kingdom
- Big Basin Redwoods State Park