Windsor, CA Vacation Rentals

Our Favorite Vacation Rentals in Windsor

  • The Eastside - Healdsburg Family Farmhouse Home
     Country House
    Booking.com
    From
    $914
  • Windsor, CA: Sonoma 1 Bedroom Condo w/Fireplace, Resort Pool, Spa, WiFi & More!
     Home/Apartment
    HolidayLettings
    From
    $242
  • 788 Magnolia Dr Entire Property Home
     Country House
    Booking.com
    From
    $1,105
  • Close to Healdsburg Plaza with Vineyard Views!
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $669
  • Wine Country Getaway! Modern Three-Unit Cottage Cottage
     Country House
    Booking.com
    From
    $288
  • Stunning vineyard views from the private deck at this wine-lovers house!
     3br Home/Apartment
    HolidayLettings
    From
    $657
  • Loch Haven Retreat
     Country House
    Booking.com
    From
    $442
  • Healdsburg Relaxing Wine Country Farmhouse
     2br Farmhouse
    HolidayLettings
    From
    $454

Check prices for these upcoming dates

Windsor Vacation Rentals with a Pool

  • Windsor Wine Country Retreat
    Excellent4br Home/Apartment
    Airbnb
    From
    $961
  • Luxury Estate Guesthouse at Viszlay Vineyards
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,610
  • Charming Guest Home in Heart of Wine Country
    Excellent2br Home/Apartment
    Airbnb
    From
    $740
  • Wine Country Retreat! Location! Pool! Hot Tub!
    Good3br Home/Apartment
    Airbnb
    From
    $777

Windsor Vacation Rentals with Wi-Fi

  • 3 bed 2 bath 1 mile from Windsor Town Green
    Excellent3br Home/Apartment
    Airbnb
    From
    $468
  • A Sunny Spacious American Home with Backyard
    Excellent4br Home/Apartment
    Airbnb
    From
    $440
  • Spacious 3 Bedroom Home Sleeps 4 Couples
    Excellent4br Home/Apartment
    Airbnb
    From
    $819
  • The Loft Under The Oaks
    ExcellentHome/Apartment
    Airbnb
    From
    $154

Windsor Pet-Friendly Vacation Rentals

  • Spacious Studio in Sonoma wine country
    Excellent-1br Home/Apartment
    Flipkey
    From
    $282
  • Cozy Cottage by the River ***Pet Friendly***
     Home/Apartment
    HolidayLettings
    From
    $220
  • Cozy riverfront cabin w/river view, access & entertainment-dogs OK
     3br Home/Apartment
    HolidayLettings
    From
    $353
  • Midcentury Cabin in the Redwoods
     2br Home/Apartment
    HolidayLettings
    From
    $432

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.

Price and Availability in Windsor

Most expensive
Most availability
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Powered by:
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.

The Weather in Windsor

Rainy days
71° 33°
7
67° 32°
4
71° 33°
7
82° 27°
0
90° 30°
8
86° 34°
4
92° 43°
0
102° 42°
0
106° 48°
0
102° 47°
0
97° 43°
0
89° 38°
1
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Windsor. The warmest months in Windsor are June and July, when temperatures reach 106 ˚F. The coolest month is November, when temperatures drop to 27 ˚F. The wettest month in Windsor is October with 8.4 inches of rain, while the driest month is August with 0.12 inches of rain.

What Expert Travelers Think

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

Vacation Rentals in Windsor

Browse rentals from all the leading providers including Airbnb, Priceline, RedAwning and others at AllTheRooms.com. We have 814 vacation rentals, hotels and other places to stay in Windsor ranging from cheap options to luxury places to stay. For those traveling on a budget, the cheapest place to stay in Windsor is available at $25 per night. An average rental in Windsor costs on average $271 per night.

Those looking to get some work done during their trip to Windsor can choose from 508 places to stay that have WiFi. 44 of our accommodations come with breakfast in the price. Choose from 395 places to stay that provide gym options, so you won't miss a single workout. Driving to Windsor? Then choose one of the 532 places to stay that comes with a parking spot included. We have 415 places to stay that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 29 accommodations that are designated as pet-friendly.

In Windsor AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 3 providers, including 533 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from RedAwning.

586 accommodations in Windsor have been reviewed; 61% are rated excellent or good. 237 places to stay in are instantly bookable.

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