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Vacation rentals in Woodside

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Top-rated vacation rentals in Woodside

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

Guesthouse in Woodside
Rustic Cabin in the Redwoods
Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.
$294 per night
Guest suite in Woodside
Stay Nestled in Ancient Redwoods in Silicon Valley
Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.
$108 per night
Guesthouse in Woodside
SkyHigh Redwoods Retreat with Bay Views
Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.
$185 per night

Stay near Woodside's top sights

Alice's Restaurant65 locals recommend
Huddart Park33 locals recommend
Wunderlich County Park46 locals recommend
Buck’s Restaurant, Woodside49 locals recommend
The Village Pub48 locals recommend
Stulsaft Park12 locals recommend

Other great vacation rentals in Woodside

Cabin in Woodside
Kings Mountain Studio Cabin
$175 per night
Guest suite in Redwood City
Very Spacious Beautiful Guest Quarter!
$158 per night
Guest suite in Woodside
Separate entry room near Stanford
$139 per night
Guesthouse in Redwood City
Quiet , Private Studio / Cottage
$109 per night
Guesthouse in San Carlos
Private Garden Cottage
$134 per night
Guesthouse in Redwood City
Soak up the Serenity on the Patio of a Charming Cottage
$98 per night
Apartment in Palo Alto
Private Studio Apartment with private entrance.
$99 per night
Guesthouse in Portola Valley
1 Bdr Cabana just west of Stanford
$250 per night
Guesthouse in Palo Alto
Renovated Guest House with AC - Downtown Palo Alto
$119 per night
Condo in Palo Alto
Perfect Location, walk to all Palo Alto venues
$199 per night
Guesthouse in Redwood City
🌼Modern guesthouse w private patio and ♨️ hot tub
$129 per night
Guesthouse in Menlo Park
Charming, modern, restorative, private studio
$100 per night

Quick stats about vacation rentals in Woodside

Total rentals

120 properties

Rentals with dedicated workspaces

70 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

5.5K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. San Mateo County
  5. Woodside