Cottage vacation rentals in Woodside

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Top-rated cottage rentals in Woodside

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Guest favorite
A private garden space features a white wicker seating arrangement, providing a comfortable area for relaxation. Colorful flags from various countries are strung overhead, adding a festive touch. Surrounding greenery enhances the tranquil ambiance, inviting guests to enjoy the outdoors.
Cottage in Alameda
4.9 out of 5 average rating, 401 reviews

Large Cottage Near SF, Beach, Airport w/ Backyard

Beautiful, spacious, and quiet cottage 1-bedroom 1-bath, 860sqft, with a private garden, located in the prestigious Alameda Gold Coast neighborhood, safe, 7miles to OAK Airport, 5miles to Oakland Coliseum, 9miles to UC Berkeley, walk to the beach, easy transportation to San Francisco by ferry, bart, or bus. It is walking to coffee shops, restaurants, grocery stores. Next to Crown beach with spectacular view of San Francisco. Parties are not allowed. Top speed Internet. Pet allowed, $50 per stay.

Guest favorite
A cozy seating area features a deep green couch adorned with vibrant cushions, complemented by two wooden side tables. A piece of artwork depicting blue-toned trees is displayed above the couch. Soft natural light filters through a nearby window, adding warmth to the space.
Cottage in Palo Alto
4.85 out of 5 average rating, 100 reviews

Cozy Cottage near Stanford

A quiet cottage is behind the main house surrounded by the redwood trees. It has two bedrooms and one bathroom that accommodates up to 4 people. Newly remodeled kitchen is equipped with brand new gas stove/oven and microwave, and everything you need. Washing machine and dryer are on site. Great location close to restaurants, coffee shops, grocery stores and Caltrain station. 3 miles to Stanford University and Shopping Center. Close to all high tech companies. 20 min from SJC and 30 min from SFO.

Guest favorite
Cottage in Palo Alto
4.85 out of 5 average rating, 141 reviews

Cozy Cottage near Stanford | Google | Meta | Tesla

Part of a beautiful newly custom built craftsman architectural style house with a private entrance. The suite is completely separated, with a secure smart-lock, nicely appointed with modern chic furnishings throughout in a sought-after neighborhood in Midtown Palo Alto - one of the best places to live in Silicon Valley. 3-5 minutes WALK to grocery store, pharmacy, coffee/tea shop, and restaurants. Within 1 or 2 miles, you can ride your BIKE or CAR to Stanford, Tesla, GOOG, Meta/FB and Amazon.

Top guest favorite
A tranquil pond is featured, with a fountain creating playful water spray that catches glimmers of sunlight. Surrounding greenery and trees are visible, while the ocean horizon is faintly seen in the distance, blending with the soft hues of a sunset.
Cottage in Pescadero
4.97 out of 5 average rating, 122 reviews

Bean Hollow West Cottage

This lovely 2 bedroom 2 bath cozy cottage is a great place to stay while exploring the beautiful coast of No. California. The cottage is tucked away in silence interrupted only by the faint sound of the distant ocean. It has a spectacular ocean view surrounded by a peaceful pond, incredible sunsets, lots of trees and wildlife. Sits 5 minutes from Bean Hollow Beach and many others minutes away between Half Moon Bay and Santa Cruz. This cottage is safe and private with beautiful outdoor living.

Top guest favorite
An open-concept living area is showcased, featuring modern cabinetry and stainless steel appliances in the kitchen. A light-colored sofa faces a wall-mounted television, with a small dining area equipped with bar stools. Natural light fills the space through multiple windows.
Cottage in Mountain View
4.92 out of 5 average rating, 193 reviews

Brand new house in Mountain View

⚽ 2026 WORLD CUP: Free Levi’s Stadium Transit! Stay in this new 2BR cottage (700+ sq ft). We offer free transit to all FIFA World Cup matches! 🏡 Prime Location • 5m to DT Mountain View & El Camino Hospital • Easy access to 101, 85 & 237 • Walk to Ranch 99, Starbucks & Cuesta Park ✨ Modern Comforts • High ceilings & open layout • Stainless steel appliances • In-unit washer/dryer • Smart lock, Nest & video doorbell 🔒 Private & Peaceful • Private entrance • Ideal for business or leisure

Top guest favorite
The exterior of the cottage features a stone-accented porch with a wooden chair, framed by lush greenery and flowering plants. A pathway of stones leads from the well-kept lawn to the entry, where large double doors invite guests inside.
Cottage in San Carlos
4.98 out of 5 average rating, 248 reviews

Carmelita Creek House

The creek house is on a beautiful tree lined street, walking distance to downtown San Carlos. The house is a spacious one bedroom cottage with designer finishes and gorgeous vaulted ceilings. You will be surrounded by mature redwoods on the peaceful balcony and one with nature at the fire pit overlooking a year round creek. Amenities include a full sized kitchen, comfortable workspace, washer/dryer, fast WiFi, cable TV and a gas fireplace. We live in the main house on the property.

Top guest favorite
A welcoming living area features a light-colored sofa with red and white cushions. A wooden coffee table with decorative items anchors the space, while vibrant flowers in a vase add a touch of color. A dining area is visible, accompanied by a side chair.
Cottage in Santa Clara
4.94 out of 5 average rating, 210 reviews

Manzanita Cottage in the Heart of Silicon Valley

*We respond to inquiries quickly! We use CDC cleaning guidelines. Our property is powered 100% by solar* The Manzanita Cottage is a perfect getaway for business or vacation travelers. The cottage is well appointed and has everything you need for an extended or short stay. This private & inviting cottage is big on amenities: stove, oven, microwave, coffee maker, dishwasher, washer & dryer, etc. We have two other units on our property: The Orchard tiny house and The Manzanita cottage.

Top guest favorite
A modern kitchen is equipped with light wood cabinetry and solid gray countertops. A large window allows natural light to fill the space, complemented by a vase of sunflowers. The kitchen features a gas stove, refrigerator, and a dishwasher for convenience.
Cottage in Golden Gate
4.95 out of 5 average rating, 125 reviews

Modern Garden Guesthouse, Step-Free

New build, all one level, no steps to entrance from street. Private quiet dedicated guesthouse. Plentiful, free street parking w/in one block. Keyless entry. 450 sq ft but feels larger. Queen bed, large closet, full kitchen, large bathroom, private patio. Free W/D. 2-55" TVs with digital antennae +Roku. Kitchen table doubles as desk. No cleaning fee. Our family plays in shared yard late afternoon with 2 friendly dogs. 7-28 days firm. For two guests, choose "2" when booking.

Top guest favorite
A welcoming front view of a single-story cottage is presented, featuring a central entrance with a decorative door. Potted flowers in vibrant colors are arranged along the walkway, complemented by a paved driveway. Lush greenery surrounds the property, creating a serene setting.
Cottage in Mountain View
4.97 out of 5 average rating, 180 reviews

Spacious Cottage w/Vaulted Ceiling

Come enjoy the peaceful seclusion of this backyard, 700sqft, cottage, in the heart of Silicon Valley. Unwind in your own private backyard nestled in the shade of fruit tree and other trees. Beautifully and fully furnished for your comfort. Conveniently located with easy commute to local high tech companies, Stanford University and train ride away to San Francisco. Pls check our other Airbnb unit < https://www.airbnb.com/rooms/36591781> if this cottage is not available.

Guest favorite
A warm wooden interior features a spacious bed adorned with a patterned comforter. A desk with a chair is situated near large windows, providing natural light. A small table and a comfortable chair complement the cozy setting.
Cottage in Palo Alto
4.88 out of 5 average rating, 222 reviews

Cozy Cottage, Private Entrance

Recently built cottage with private entrance, queen bed, desk and 500 Mb/s Wifi. The private bathroom and private kitchenette are four feet from the cottage entrance. The cottage is stand-alone, and the kitchenette and bathroom have been sealed from the rest of the main house for safety. The space will be guaranteed to be unoccupied for 3 days before your checkin and thoroughly disinfected. Bedding includes a new Sealy Posturepedic box springs and mattress (firm).

Top guest favorite
A cozy cabin exterior is set among tall trees, featuring a stone patio with two Adirondack chairs. The structure has large windows that invite natural light, while the surrounding landscape includes rocks and pine needles, creating a natural and serene environment.
Cottage in Boulder Creek
4.98 out of 5 average rating, 130 reviews

Creekside Bliss #1 - The Santa Cruz

Santa Cruz County Vacation Rental Permit# 191283. Newly remolded beachy creek side cottage, bright and airy, fully equipped kitchen. Located in the Santa Cruz mountains 1/2 mile from downtown Boulder Creek on a secluded property. Close to many event and wedding venues. Fifteen minute drive to Big Basin State Park, 30 minutes to Santa Cruz and Beach Boardwalk, close to many wineries and lots of hiking trails. Twenty minutes from Roaring Camp Railroad.

Top guest favorite
An open living space features a wooden cabinet, a light-colored sofa, and a round coffee table on a circular rug. Sunlight streams in through multiple clerestory windows, illuminating the natural wood ceiling and warm hardwood floor.
Cottage in Noe Valley
4.98 out of 5 average rating, 244 reviews

Hand Crafted Cottage

Nestled at the top of a hill above Noe Valley, our cottage features an open environment with plenty of natural light, and all custom made furniture including a lovely kitchenette, bathroom, and garden, all within easy access to public transportation. Registration Number2021 - 005037STR ***Due to COVID 19, we are taking extra precaution and following Airbnb's new cleaning guidelines. Please contact us if you have any additional concerns***

Popular amenities for Woodside cottage rentals

Quick stats about cottage rentals in Woodside

  • Nightly prices starting at

    Woodside vacation rentals start at G$33,472 GYD per night before taxes and fees

  • Verified guest reviews

    Over 220 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodside rentals

  • 4.9 Average rating

    Woodside stays are highly rated by guests—averaging 4.9 out of 5!

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