Woodside places to stay

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Top-rated places to stay in Woodside

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 296 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Feb 1 – 8

G$22,659 GYD per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

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.

Jun 7 – 14

G$70,056 GYD per night

Guest favorite

Guesthouse in San Carlos

4.99 out of 5 average rating, 588 reviews

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Jul 6 – 13

G$31,986 GYD per night

Guest favorite

Cabin in Woodside

4.97 out of 5 average rating, 342 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Jan 28 – Feb 4

G$37,682 GYD per night

Guest favorite

Guest suite in Woodside

4.88 out of 5 average rating, 339 reviews

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.

May 28 – Jun 4

G$25,425 GYD per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 408 reviews

Separate entry room near Stanford

This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

Jul 6 – 13

G$33,375 GYD per night

Guest favorite

Guest suite in Redwood City

4.94 out of 5 average rating, 294 reviews

Beautiful Studio

Studio with a private entrance, your own private kitchen, dining area and all cooking utensils, fully equipped. TV 50” with roku, netflix, amazon prime through WiFi. The studio has its own separate heating unit and AC. Bath robes and feather down-quality linen. Well insulated, wheelchair ok Code operated, lock door Minutes away from Stanford. We use eco-friendly cleaning products. Easy parking always available. Comfortable queen bed. Portable cot and bedding available upon request.

Sep 3 – 10

G$25,776 GYD per night

Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 152 reviews

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.

Sep 16 – 23

G$39,929 GYD per night

Guest favorite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 146 reviews

Elegant retreat in Redwood City

Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. All furnishings are selected by a professional decorator and routinely upgraded. This is part of a ~4000 sq ft luxury single family home with 2 completely separate and private entrances.

Dec 15 – 22

G$25,730 GYD per night

Guest favorite

Guesthouse in Woodside

4.94 out of 5 average rating, 106 reviews

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

Oct 1 – 8

G$87,750 GYD per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 382 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Apr 14 – 21

G$24,237 GYD per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 483 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Jan 25 – Feb 1

G$43,140 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Woodside places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Woodside's top sights

Huddart Park33 locals recommend

Alice's Restaurant65 locals recommend

Wunderlich County Park46 locals recommend

Buck’s Restaurant, Woodside49 locals recommend

The Village Pub48 locals recommend

Roberts Market & Liquor28 locals recommend

Other great vacation rentals in Woodside

Guest favorite

Guesthouse in Redwood City

4.94 out of 5 average rating, 173 reviews

Detached Guest House With Views

May 8 – 15

G$29,503 GYD per night

Guest favorite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 386 reviews

Private cottage in a garden

Feb 5 – 12

G$24,436 GYD per night

Guest favorite

Home in Redwood City

4.97 out of 5 average rating, 289 reviews

Private suite

Jul 3 – 10

G$30,398 GYD per night

Guest favorite

Guest suite in Menlo Park

4.88 out of 5 average rating, 104 reviews

New studio apt--walk to Stanford

Dec 24 – 31

G$22,276 GYD per night

Guest favorite

Guesthouse in Redwood City

4.95 out of 5 average rating, 503 reviews

Stylish Separate Loft/Cottage Walk to Redwood City

May 30 – Jun 6

G$31,377 GYD per night

Guest favorite

Guesthouse in Portola Valley

4.94 out of 5 average rating, 167 reviews

Woodsy Silicon Valley Cottage

Jun 17 – 24

G$31,439 GYD per night

Guest favorite

Guest suite in Palo Alto

5.0 out of 5 average rating, 176 reviews

Savvy Studio ❤︎ Palo Alto ❤︎ of Silicon Valley

Sep 20 – 27

G$28,351 GYD per night

Guest favorite

Guesthouse in Hillsborough

4.95 out of 5 average rating, 809 reviews

Little Cottage on the Hill

Oct 25 – Nov 1

G$28,217 GYD per night

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Other great vacation rentals in Woodside

Guest favorite

Condo in Redwood City

4.93 out of 5 average rating, 104 reviews

Cozy Entire 1-Bedroom Condo in Redwood City

Sep 11 – 18

G$36,705 GYD per night

Guest favorite

Guest suite in Scotts Valley

4.96 out of 5 average rating, 629 reviews

Snug and Cozy between the Skyline and the Sea

Oct 9 – 16

G$15,819 GYD per night

Guest favorite

Camper/RV in La Honda

4.99 out of 5 average rating, 112 reviews

40 Acre Redwood Forest With Private Trails

Mar 23 – 30

G$32,154 GYD per night

Guest favorite

Guest suite in East Palo Alto

4.91 out of 5 average rating, 127 reviews

Cozy studio own entry, patio, next to FB, Stanford

Feb 11 – 18

G$19,236 GYD per night

Guest favorite

Guest suite in Belmont

4.95 out of 5 average rating, 101 reviews

Cozy private in-law suite, close to SFO, fast WiFi

Aug 12 – 19

G$25,975 GYD per night

Guest favorite

Guest suite in Boulder Creek

4.98 out of 5 average rating, 428 reviews

Enjoy Private Redwoods from Your Bed or the Deck

Aug 30 – Sep 6

G$28,811 GYD per night

Guest favorite

Apartment in Woodside

4.89 out of 5 average rating, 35 reviews

Cozy country Woodside home

Jun 20 – 27

G$29,577 GYD per night

Guest favorite

Cottage in Woodside

5.0 out of 5 average rating, 19 reviews

Exquisite luxury executive 2-suite cottage

Oct 6 – 13

G$211,395 GYD per night

Show all

Quick stats about vacation rentals in Woodside

Total rentals
120 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
5.6K reviews

Frequently Asked Questions

Where should I stay in Woodside?
Make yourself at home in Woodside by choosing from our most frequently booked neighborhoods. We have over 1,050 vacation rentals in Farm Hill, over 930 vacation rentals in Woodside Hills, and over 930 vacation rentals in Woodside Plaza.
How much does it cost to stay in guesthouse rentals in Woodside?
Experience the best of Woodside with our guesthouse rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there guesthouse rentals with a dedicated workspace in Woodside?
Yes! Work meets play with ease at over 10 guesthouse rentals in Woodside featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Woodside have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Woodside. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Woodside?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 50 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Woodside have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Woodside. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Woodside?
Four-legged friends are welcome in Woodside. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there Woodside vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Woodside, available on Airbnb. Make a splash and soak up the sun in style!
Do private suite rentals in Woodside have wifi?
Absolutely! We offer over 10 private suite rentals with wifi in Woodside. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Woodside?
Woodside has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Woodside places to stay

Top-rated places to stay in Woodside

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Woodside places to stay

Stay near Woodside's top sights

Other great vacation rentals in Woodside

Guesthouse in Redwood City

Guesthouse in Sunnyvale

Home in Redwood City

Guest suite in Menlo Park

Guesthouse in Redwood City

Guesthouse in Portola Valley

Guest suite in Palo Alto

Guesthouse in Hillsborough

Other great vacation rentals in Woodside

Condo in Redwood City

Guest suite in Scotts Valley

Camper/RV in La Honda

Guest suite in East Palo Alto

Guest suite in Belmont

Guest suite in Boulder Creek

Apartment in Woodside

Cottage in Woodside

Quick stats about vacation rentals in Woodside

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Woodside?

How much does it cost to stay in guesthouse rentals in Woodside?

Are there guesthouse rentals with a dedicated workspace in Woodside?

Do house rentals in Woodside have a bbq area?

What are the most popular amenities for House Rentals in Woodside?

Do house rentals in Woodside have air conditioning?

Are there pet-friendly vacation rentals in Woodside?

Are there Woodside vacation rentals on Airbnb with pools?

Do private suite rentals in Woodside have wifi?

Are there family-friendly house rentals in Woodside?

Destinations to explore