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Windsor, CA Vacation Rentals

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Our Favorite Vacation Rentals in Windsor

  • 3BR w/ Pool, Hot Tub & Guest Suite
     3br Home/Apartment
    RedAwning
    From
    $1,406
  • The Eastside - Healdsburg Family Farmhouse Home
     Country House
    Booking.com
    From
    $729
  • Windsor, CA Cottage in Sonoma's Wine Country
    Excellent2br Cottage
    HolidayLettings
    From
    $428
  • Quiet Wine Country Home w/ Private Pool & Hot Tub
     4br Home/Apartment
    RedAwning
    From
    $1,156
  • Quiet Wine Country Home Home
     Country House
    Booking.com
    From
    $679
  • Windsor, CA: Sonoma 3 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!
     3br Home/Apartment
    HolidayLettings
    From
    $263
  • 4BR Rocktop Lodge w/ Pool & Hot Tub
     4br Home/Apartment
    RedAwning
    From
    $1,428
  • Loch Haven Retreat
     Country House
    Booking.com
    From
    $649
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Check prices for these upcoming dates

Windsor Vacation Rentals with a Pool

  • Windsor 2 bdrm condo, Rare Find
    Excellent2br Home/Apartment
    Airbnb
    From
    $451
  • Windsor Wine Country Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $961
  • Luxury Estate Guesthouse at Viszlay Vineyards
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,553
  • 2Bdm Condo Windsor WorldMark#8
     2br Home/Apartment
    Airbnb
    From
    $466
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Windsor Vacation Rentals with Wi-Fi

  • Sunny Sonoma 1950s Ranch
     2br Home/Apartment
    RedAwning
    From
    $526
  • Lovely 2BR Cottage in Wine Country w/ Porch
     2br Home/Apartment
    RedAwning
    From
    $479
  • Sonoma Wine Country Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $213
  • The Doll House
    Excellent2br Home/Apartment
    Airbnb
    From
    $226
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Windsor Pet-Friendly Vacation Rentals

  • Close to Healdsburg Plaza with Vineyard Views!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $824
  • Stunning vineyard views from the private deck at this wine-lovers house!
     3br Home/Apartment
    HolidayLettings
    From
    $689
  • Spacious Studio in Sonoma wine country
    Excellent-1br Home/Apartment
    Flipkey
    From
    $276
  • Cozy Cottage by the River ***Pet Friendly***
     Home/Apartment
    HolidayLettings
    From
    $220
Show all

Windsor Travel Guide

Windsor is a beautiful larger town in central California just a few miles north of Santa Rosa. Windsor was settled in the mid 1800s by Europeans and soon after it started to grow into a larger town. It is named Windsor because Hiram Lewis, the postmaster from England, said the town reminded him of the grounds of Windsor Castle. Unfortunately, the blooming city was destroyed in a fire in 1905, and it was in dire need of repair. The town was saved by highway construction investors and soon the town was connected to major cities. Windsor was and still is a farming town where a large part of the area is dedicated to crops, apple farms, and grape yards. Due to this agricultural production there are a lot of wineries and farmer's markets in the area, so if you like to sit down and enjoy a great glass of wine or attend to a wine tasting event, this is a good place to do so. For the more active types, there are tons more activities here in Windsor.

Things to Do in Windsor

Lots of amazing things await visitors at Windsor! This town has two main categories of activities: outdoor exploration, and culinary tourism. If you like either of those then Windsor is an excellent spot for you! Moreover, if you would like to combine these two activities check out the Ace It Bike Tours where visitors bike around the grape vineyards, and at the end of the tour visitors will try the various types of wines. Moreover, the Foothill Regional Park is a beautiful hilly park where trails and ponds are ready for exploration. Go on an amazing horseback riding tour and have a wonderful time in the gorgeous California setting. Additionally, if you like water sports make sure to try out the Russian River Paddle Boards Adventures where you can go on a tour and explore the river and the surrounding area on a paddle board. Furthermore, since this region is famous for the great wineries, attend an amazing wine tasting where you can learn about the production process, the different types of grapes, and how to tell the difference between various wines. Da Vine Wine Tours is an excellent tour to attend where you can enjoy the breathtaking views while sipping on various wines.

Best Places to Stay in Windsor

The best area to stay is the Foothill area where you can be close to a beautiful park and nearby restaurants. Plenty of shops and stores are also just a few miles away so you do not have to go very far for anything. There are many vacation rentals in Windsor, so if you are looking for the perfect vacation home you do not have to worry. Rental homes most often feature full kitchens, nice dining areas, and a great location. Furthermore, if you are looking for a house rental with your family and friends, check out the options for luxury condo rentals too. Plenty of great vacation home rentals await you, so just browse our listings and find your favorite one.

Best Time to Visit Windsor

The average yearly temperature is 64 degrees in Windsor, so it is a pretty great place to visit all year around. However, if you are going for summer activities and want to visit the nearby beaches and waterparks, plan your trip in August or September when the average temperature is 78 degrees and there is very little chance for rain. The rest of the year is pretty rainy, so if you are traveling outside of the summer months pack up some raincoats.

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Price and Availability in Windsor

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

Rainy days
70° 27°
9
70° 27°
9
80° 32°
10
98° 42°
1
70° 27°
9
70° 27°
9
70° 27°
9
105° 50°
0
105° 41°
0
70° 27°
9
70° 27°
9
70° 27°
9
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Windsor. The hottest month in Windsor is April, when temperatures peak at 105 ˚F. The coolest month is January, when temperatures drop to 27 ˚F. The wettest month in Windsor is October with 9.54 inches of rain, while the driest month is September with 1.32 inches of rain.

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What Expert Travelers Think

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  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
    The Rare Welsh Bit

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

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Vacation Rentals in Windsor

Browse accommodations from all your favorite providers including Airbnb, Priceline, RedAwning and others at AllTheRooms.com. Windsor has 770 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those traveling on a budget, the cheapest place to stay in Windsor is available at $38 per night. In general, a place to stay in Windsor will cost you $274 per night.

If you need to stay connected during your trip, then you can choose from over 498 accommodations in Windsor that have WiFi. 39 places to stay include a breakfast. You can maintain your workout regime by staying at one of 390 accommodations that provide gym facilities. If you are driving to Windsor, you'll want to pick from 517 places to stay that provide parking. We have 408 places to stay that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to choose one of the 31 pet-friendly accommodations available.

576 of the accommodations in Windsor have been reviewed and rated. 62% are rated excellent or good. 232 places to stay in are instantly bookable.

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