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Cupertino Vacation Rentals

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Our Favorite Vacation Rentals in Cupertino

  • Roseview: Dazzling Gem in the Heart of San Jose
     4br Home/Apartment
    RedAwning
    From
    $1,068
  • Modern Townhome near Apple Campus
     Home/Apartment
    Booking.com
    From
    $270
  • Beautiful rooms with garden view in an organic house in Cupertino
     2br Home/Apartment
    HolidayLettings
    From
    $238
  • Astonishing! Bright! Spacious, Modern Condo!
     2br Home/Apartment
    RedAwning
    From
    $569
  • 4 bedrooms with 2 bathrooms in a Decent house
     Country House
    Booking.com
    From
    $63
  • Exquisite Private Studio
     -1br Studio
    HolidayLettings
    From
    $316
  • Separate access to private rooms - Apple Park
     Home/Apartment
    Booking.com
    From
    $141
  • Sakura room
     Home/Apartment
    HolidayLettings
    From
    $94
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Check prices for these upcoming dates

Cupertino Vacation Rentals with a Pool

  • A Private room NR Apple and De Anza
     Home/Apartment
    Airbnb
    From
    $107
  • Remodeled 2BR/2BA in Close to Apple HQ
     2br Home/Apartment
    Airbnb
    From
    $198
  • Private & Quiet Garden Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $239
  • Minimalist 1BR Apartment 15 minutes from SJC!
    ExcellentHome/Apartment
    Airbnb
    From
    $151
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Cupertino Vacation Rentals with Wi-Fi

  • Private 2 bedroom Bungalow walk to Apple
    Excellent2br Home/Apartment
    Airbnb
    From
    $240
  • Beautiful one bedroom in Cupertino, Bay Area
    ExcellentHome/Apartment
    Airbnb
    From
    $154
  • Mid Century Modern Guesthouse
    ExcellentHome/Apartment
    Airbnb
    From
    $205
  • SFH Walk to Cupertino Apple HQ, AC, Clean & Comfy
    Excellent3br Home/Apartment
    Airbnb
    From
    $290
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Cupertino Pet-Friendly Vacation Rentals

  • Global Luxury Suites at Downtown Mountain View
     Home/Apartment
    HolidayLettings
    From
    $389
  • Silicon Valley Luxury Home in Heart of Los Altos - Minutes to Stanford Palo Alto
     5br Home/Apartment
    HolidayLettings
    From
    $1,121
  • Palo Alto Apt. - Walk to Stanford & Restaurants!
    NiceHome/Apartment
    HolidayLettings
    From
    $266
  • Business Ready 2BR w/ Fast Internet - Kasa
     2br Home/Apartment
    HolidayLettings
    From
    $441
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Cupertino Travel Guide

Cupertino is located in Santa Clara County right next to San Jose. The city is also right under the wild Santa Cruz Mountains; an excellent place for outdoor activities. Cupertino is part of the Silicon Valley and it is home to the Apple’s headquarters. Interestingly, Cupertino was a small, rural village until the end of the 19th century, but as soon as railroads reached the village it started to develop and grow fast. But the true development and expansion of housing didn't occure until the mid 20th century. Ever since the city has kept growing and developing, welcoming the diverse tech work force that is from all over the world.

Things to Do in Cupertino

Cupertino is not only beautiful but also very interesting because of its place at the forefront of technological advancement. There are also plenty of options for outdoor activities, so the adevnturous types should love Cupertino. Start the Cupertino journey at the Apple Park Visitors Center. The center is an extension of the Apple campus and allows visitors to explore, learn about, and experience Apple's culture (and maybe their plans for world domination). Here guests can purchase various Apple products, see the Apple exhibition, and get cozy on the rooftop terrace. The terrace grants visitors the opportunity to sip on a coffee while overlooking the Infinite Loop Headquarters of Apple, which some say looks like a spaceship.

Another interesting landmark is San Jose's Winchester Mystery House, just a quick drive from Cupertino. While it may just look like an old mansion really it is also the home of some paranormal activity. Built by the wealthy widow of the Winchester fortune there are many oddities like stairs that go nowhere and secret windows looking into rooms throughout the house. There are daily tours which will speak about these peculiarities and talk about the alleged ghosts that live here. The Mystery House is also across the street from Santana Row, an upscale shopping area.

To spend some time outdoors and take advantage of California's weather, visit Rancho San Antonio County Park. The park features a 25 mile long hiking trail and excellent views of the bay. In the heart of the city is Cupertino Memorial Park. A lovely little duck pond, picnic areas, and walking paths are all available for entertainment. The Fujitsu Planetarium is an awesome place to learn about the stars and spend an eye opening afternoon.

Best Places to Stay in Cupertino

The best vacation rentals are near Creekside or the eastern districts where restaurants, cafes, stores, landmarks, and much more are in walking distance. The Stevens Creek area has a large nature preserve essentially in its backyard.

Best Time to Visit Cupertino

The heaviest rain lasts from around April to November, the remaining months are often quite lovely with temperate temperatures ideal for a hike or visiting a nearby winery.

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Price and Availability in Cupertino

Most expensive
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The cheapest day to stay at a vacation rental in Cupertino tends to be Saturday, while the most expensive day tends to be Friday. Vacation homes in Cupertino tend to be busiest on Wednesdays, while it tends to be much quieter on Saturdays.
The most expensive month to stay in a vacation rental in Cupertino is in July, while the cheapest month is in April. The most popular time to book a vacation rental in Cupertino is in the high season in June. Cupertino has its low season in December, when less people are visiting and the vacation home occupancy rate drops.
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The Weather in Cupertino

Rainy days
67° 32°
3
64° 33°
5
75° 40°
3
89° 47°
0
76° 45°
1
101° 52°
0
89° 56°
0
95° 58°
0
97° 47°
0
90° 37°
0
76° 34°
2
67° 34°
4
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Cupertino. The warmest months in Cupertino are July and April, when temperatures reach 101 ˚F. The coolest month is December, when temperatures drop to 32 ˚F. The wettest month in Cupertino is November with 5.18 inches of rain, while the driest month is September with 0.25 inches of rain.

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What Expert Travelers Think

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  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

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Vacation Rentals in Cupertino

Browse rentals from all the leading providers including Airbnb, Priceline, Agoda and others at AllTheRooms.com. Cupertino has 714 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. A vacation in Cupertino can be budget-friendly - the lowest price vacation rental is available at $15 a night. An average vacation rental in Cupertino costs on average $142 a night.

Those needing to get some work done during their trip to Cupertino can pick from 463 places to stay that have WiFi. 39 of our accommodations come with breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 88 accommodations that have gym facilities. Driving to Cupertino? Then choose one of the 415 places to stay that comes with a parking spot included. 73 vacation rentals come with a pool or jacuzzi

AllTheRooms has 71 pet-friendly places to stay in Cupertino, so if you're traveling with your pet you won't have any trouble.

AllTheRooms compares vacation rentals, hotels and other unique accommodation types from many providers in Cupertino, including 459 places to stay from Airbnb, 10 accommodations from Priceline and 3 places to stay from Agoda

404 of the places to stay in Cupertino have been reviewed by previous guests. They rated 60% as excellent or good. You can instantly book any of 233 places to stay right now.

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