Woodside places to stay

Book unique places to stay, houses, and more on Airbnb

Top-rated places to stay in Woodside

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

Guest favorite
Guesthouse in Redwood City
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.
Dec 4 – 11
ﺩ.ﺇ347 per night
4.92 out of 5 average rating, 292 reviews
Guest favorite
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.
Jun 6 – 13
ﺩ.ﺇ1,078 per night
4.99 out of 5 average rating, 275 reviews
Guest favorite
Guesthouse in San Carlos
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.
May 27 – Jun 3
ﺩ.ﺇ492 per night
4.99 out of 5 average rating, 579 reviews

Popular amenities for Woodside places to stay

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
Guest suite in Redwood City
Beautiful Studio
Sep 18 – 25
ﺩ.ﺇ399 per night
4.93 out of 5 average rating, 292 reviews
Guest favorite
Guesthouse in Atherton
Charming Cottage near Stanford in Lovely Garden
Oct 17 – 24
ﺩ.ﺇ593 per night
4.99 out of 5 average rating, 172 reviews
Guest favorite
Home in Redwood City
Private suite
Sep 27 – Oct 4
ﺩ.ﺇ453 per night
4.97 out of 5 average rating, 287 reviews
Guest favorite
Guest suite in Palo Alto
Savvy Studio ❤︎ Palo Alto ❤︎ of Silicon Valley
Jun 26 – Jul 3
ﺩ.ﺇ458 per night
5.0 out of 5 average rating, 165 reviews
Guest favorite
Guesthouse in Portola Valley
Woodsy Silicon Valley Cottage
May 16 – 23
ﺩ.ﺇ624 per night
4.94 out of 5 average rating, 166 reviews
Guest favorite
Guesthouse in Menlo Park
Charming, modern, restorative, private studio
Feb 15 – 22
ﺩ.ﺇ364 per night
4.95 out of 5 average rating, 150 reviews
Guest favorite
Guesthouse in Redwood City
Modern Studio Cottage with Private Entrance
Dec 4 – 11
ﺩ.ﺇ400 per night
4.88 out of 5 average rating, 150 reviews
Guest favorite
Guesthouse in Hillsborough
Little Cottage on the Hill
May 2 – 9
ﺩ.ﺇ437 per night
4.95 out of 5 average rating, 801 reviews
Guest favorite
Guesthouse in Sunnyvale
Private cottage in a garden
Oct 4 – 11
ﺩ.ﺇ375 per night
4.96 out of 5 average rating, 385 reviews
Guest favorite
Home in Belmont
Hidden French Gem ~ near Caltrain, SFO
Jun 21 – 28
ﺩ.ﺇ476 per night
4.93 out of 5 average rating, 321 reviews
Guest favorite
Guesthouse in Redwood City
Stylish Separate Loft/Cottage Walk to Redwood City
Sep 2 – 9
ﺩ.ﺇ481 per night
4.95 out of 5 average rating, 500 reviews
Guest favorite
Home in Montara
A private beachy pad in Montara
Apr 24 – May 1
ﺩ.ﺇ425 per night
4.98 out of 5 average rating, 266 reviews

Other great vacation rentals in Woodside

Guest favorite
Cabin in La Honda
Coastal Redwood Getaway on a Creek
Oct 10 – 17
ﺩ.ﺇ1,363 per night
4.99 out of 5 average rating, 129 reviews
Guest favorite
Guesthouse in Portola Valley
1 Bdr Cabana just west of Stanford
Dec 17 – 24
ﺩ.ﺇ780 per night
4.98 out of 5 average rating, 174 reviews
Guest favorite
Guesthouse in Belmont
A Comfortable & Private Guest House
Dec 25 – Jan 1
ﺩ.ﺇ366 per night
4.97 out of 5 average rating, 359 reviews
Guest favorite
Guest suite in Redwood City
Private Elegant Studio in Silicon Valley
Apr 8 – 15
ﺩ.ﺇ298 per night
4.92 out of 5 average rating, 104 reviews
Guest favorite
Guest suite in Palo Alto
Cozy Getaway Suite w/Private Entry Near Stanford
Jun 9 – 16
ﺩ.ﺇ342 per night
4.95 out of 5 average rating, 128 reviews
Guest favorite
Guesthouse in Woodside
Private cottage in the woods
May 26 – Jun 2
ﺩ.ﺇ416 per night
4.97 out of 5 average rating, 90 reviews
Guest favorite
Apartment in Woodside
Cozy country Woodside home
Jul 20 – 27
ﺩ.ﺇ450 per night
4.88 out of 5 average rating, 34 reviews
Guest favorite
Guesthouse in Woodside
A beautiful Tree house -your own retreat
Sep 24 – Oct 1
ﺩ.ﺇ1,350 per night
4.94 out of 5 average rating, 100 reviews
Guest favorite
Home in Woodside
Luxury Mid-Century Modern Home w/ XL Deck
Apr 27 – May 4
ﺩ.ﺇ3,096 per night
4.96 out of 5 average rating, 27 reviews
Guest favorite
Cottage in Woodside
Exquisite luxury executive 2-suite cottage
Jan 12 – 19
ﺩ.ﺇ3,151 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Tiny home in La Honda
Delightful Tiny Home in the Redwoods !
Oct 26 – Nov 2
ﺩ.ﺇ371 per night
4.92 out of 5 average rating, 59 reviews
Guest favorite
Home in Woodside
Redwood Forest Retreat with Five Bedrooms
Jul 2 – 9
ﺩ.ﺇ2,402 per night
4.95 out of 5 average rating, 56 reviews

Quick stats about vacation rentals in Woodside

Total rentals

130 properties

Rentals with dedicated workspaces

80 properties have a dedicated workspace

Rentals with a pool

20 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

5.6K 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 1,070 vacation rentals in Farm Hill, over 950 vacation rentals in Woodside Plaza, and over 950 vacation rentals in Woodside Hills.

  • How much does it cost to stay in private suite rentals in Woodside?

    Experience the best of Woodside with our private suite rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Woodside?

    Yes! Work meets play with ease at over 20 house 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 Guesthouse Rentals in Woodside?

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, 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 house rentals in Woodside?

    Four-legged friends are welcome in Woodside. Choose from more than 10 house 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.

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