Guesthouse vacation rentals in Oakland

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Top-rated guesthouses in Oakland

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

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Guest favourite

Guesthouse in Oakland

4.93 out of 5 average rating, 427 reviews

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!

Jul. 16 – 23

$219 CAD per night

Guest favourite

Guesthouse in Berkeley

4.98 out of 5 average rating, 522 reviews

The Cottage at Squirrel End

10 min. walk to Ashby BART; average ride into SF - about 20 min. Emeryville Amtrak Station, Oakland, U.C. Berkeley - all close by. Dedicated parking space, private gated keypad entry through black bamboo & rose hedges. Originally envisioned as a romantic bedroom, the cottage is also equipped for working travelers. Large bathroom can be opened to secluded courtyard garden. WiFi, fridge, microwave, coffee. Walk to: Berkeley Bowl market, Creekwood Restaurant, cafes, deli, coffee, bike rentals.

Feb. 5 – 12

$203 CAD per night

Guest favourite

Guesthouse in Oakland

4.85 out of 5 average rating, 280 reviews

Rockridge Garden Cottage

The cottage is newly remodeled as of March 2022 and now has its own kitchen and bathroom. It is a separate unit in my backyard with vaulted ceilings which gives a spacious feel and french doors that open onto the lush garden. Queen size high end natural organic fiber bed (Earthsake.com), with down comforter + 4 pillows. Dining table and stools. LCD TV, clothes valet, work desk and great internet. Its very quiet and my guests seem to love having a private retreat type space to themselves.

Sep. 22 – 29

$220 CAD per night

Guest favourite

Guesthouse in Oakland

4.97 out of 5 average rating, 159 reviews

The Redwood Retreat

Near Lake Temescal, Redwd Regional Prk, Bart, Hwy 13, Rockridge,Montclair, Dwntwn. We completely remodeled our guest house with a focus on short term tenants. Lots of storage within one of the most quite settings you will find. We made a thoughtful attempt to load the unit with everything u might need while away. The kitchen is functional to the point that you could actually cook a Thanksgiving dinner, multiple frying pans to crock pots a blender or chefs knives. Bathroom sundries abound!

Dec. 12 – 19

$215 CAD per night

Guest favourite

Guesthouse in Oakland

4.98 out of 5 average rating, 262 reviews

Modern, bright Rockridge studio with patio.

Brand new renovated modern studio apartment, with lots of light and an open layout featuring full kitchen, dishwasher, and washer/dryer in the unit. Designed as a luxury cottage for family visits, this cozy space feels very open, with skylights and French doors that open onto a patio with seating and gas grill. Quiet and private - the entrance is at the end of a long driveway - and ideally located within easy walking distance of BART, bus routes, College Ave and 24 to the Bay Bridge.

May 16 – 23

$219 CAD per night

Guest favourite

Guesthouse in Oakland

4.92 out of 5 average rating, 228 reviews

Private, Detached, Urban Creekside Studio.

This unique, well equipped, cute little studio (that we love) is detached and fenced off from our main house. It has a separate entrance through a side gate and it's own private rear deck, with a seating and dining area... that overlooks Sausal Creek and Dimond Park. The tall willow that grows along the creek gives the deck the perfect amount of privacy and with the tranquil sound of the creek flowing (not during dry season) you would almost forget you are in an urban city.

Oct. 2 – 9

$169 CAD per night

Guest favourite

Guesthouse in Oakland

4.96 out of 5 average rating, 181 reviews

Charming Cozy Cottage in Eco-Garden Oasis

Our charming cottage is a relaxing retreat in the city! Our sweet cabin is small and cozy set in an expansive garden oasis. We offer a unique experience for those interested in a beautiful and tranquil escape in the heart of city. The cottage is at the back of our large garden with views of our beautiful urban farm with a pond with croaking frogs, chickens and goats! Couples and families with up to 2 children are best suited for this space. No more than 2 adults please.

Aug. 19 – 26

$169 CAD per night

Guest favourite

Guesthouse in Oakland

4.92 out of 5 average rating, 254 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.

Jul. 24 – 31

$176 CAD per night

Guest favourite

Guesthouse in Oakland

4.98 out of 5 average rating, 429 reviews

Garden cottage in convenient Oakland location.

You’ll love my place because of the good location, convenience to public transport, the friendly neighborhood, the ambiance.. My place is good for couples, solo adventurers, business travelers, and families (with kids). Although there is just one bedroom, the couch folds down for extra sleeping space. Please be aware that the property is in a hilly area and that there are stairs to navigate which can be challenging if you have large luggage or mobility issues.

Mar. 22 – 29

$120 CAD per night

Guest favourite

Guesthouse in Oakland

4.96 out of 5 average rating, 489 reviews

Lakeshore Cottage

Our quiet studio cottage is located in the Lakeshore/Grand Ave area of Oakland. The neighborhood is safe and beautiful and the cottage is neat and easily accessible. There is a large bright main room and a spacious bathroom that was recently updated. The cottage includes a mini kitchen. The location is close to downtown Oakland, Berkeley and San Francisco.

Sep. 19 – 26

$162 CAD per night

Guest favourite

Guesthouse in Oakland

4.95 out of 5 average rating, 261 reviews

Private Garden Studio, fast wifi near Bart

Newly remodeled home located in the popular Mosswood neighborhood, next to Temescal. 10 min walk to Sprouts Farmers Market, Boutiques & Restaurants on Piedmont Ave and MacArthur Bart Station.(to San Francisco easily) 10 min drive to Lake Merritt, Downtown Oakland and Oakland Chinatown.

May 21 – 28

$190 CAD per night

Guest favourite

Guesthouse in Kensington

4.94 out of 5 average rating, 605 reviews

Secluded luxury cottage & hot tub

Surrounded by trees on 1/2 acre, our cottage in Kensington/ Berkeley Hills is a perfect country house in the city. Our relaxing light-filled retreat is decorated with our original textile designs, Kiran's fine art photography and has a hot tub available for the guests under the stars.

Feb. 10 – 17

$239 CAD per night