Windsor vacation rentals

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Top-rated vacation rentals in Windsor

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 681 reviews

Sun Drenched Flat

Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.

Apr 14 – 21

R2,642 ZAR per night

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 250 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Oct 2 – 9

R3,626 ZAR per night

Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 361 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

Sep 19 – 26

R2,430 ZAR per night

Guest favorite

Home in Windsor

4.99 out of 5 average rating, 101 reviews

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

Oct 14 – 21

R8,859 ZAR per night

Guest favorite

Guesthouse in Santa Rosa

4.88 out of 5 average rating, 1040 reviews

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

Apr 14 – 21

R2,041 ZAR per night

Guest favorite

Home in Windsor

4.96 out of 5 average rating, 380 reviews

Winelight Vineyard Home With Spa

Available for minimum 3 day rental. Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

Nov 7 – 14

R4,221 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 325 reviews

The Suite Life! Permit Number#SVR22-078

Our private Airbnb is an extremely comfortable guest suite of over 700 square feet with air conditioning and a gas fireplace. It's beautifully decorated with a large sofa and dining area. You'll have complete privacy with your own entrance and parking space plus free WiFi. Located in a beautiful area. World class wineries, and parks are minutes away. Please feel free to message Janette with any questions about the suite! Permit Number#SVR22-078

Sep 28 – Oct 5

R2,613 ZAR per night

Superhost

Home in Healdsburg

4.81 out of 5 average rating, 424 reviews

C - Wineries/breweries seconds away

Great location for a wine country getaway! Please use the Airbnb app for self check-in instructions! The owner is severely allergic to animals, so please do not request or bring any animal with you. We have an automated backup generator for loss of power issues! Full kitchen, Outdoor patio, BBQ, Fire pit (propane tank included but not fuel), Two bikes included in stay. California King Tempurpedic bed. Laundry room, Fully renovated bathroom.

Feb 18 – 25

R3,031 ZAR per night

Guest favorite

Apartment in Santa Rosa

4.99 out of 5 average rating, 255 reviews

Robin's Nest

Our home is a 10 minute drive to downtown Santa Rosa, where you will find Russian River Brewing Company, 45 minute drive to the coast, and a little over an hour to San Francisco. The apartment is above our 2 car garage. It's a quiet 1 bedroom, 1 bath, living room, full kitchen and dining area. A twin size daybed is in the living room. Local grocery stores are within a mile, and close to Sonoma County wineries, breweries and hiking trails.

Mar 30 – Apr 6

R2,241 ZAR per night

Guest favorite

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 675 reviews

Wine Country guest house

This large private studio apartment is modern and cozy. You are next to beautiful country side while you are in the city. There is a large patio for you to relax and enjoy the beautiful wine country view. You can drive or ride your bike to Sonoma Wine Country at HWY 12 or to Russian River Brewery. The Listing excludes Tax.

Dec 15 – 22

R2,072 ZAR per night

Guest favorite

Loft in Windsor

4.81 out of 5 average rating, 500 reviews

The Loft Under The Oaks

Smack dab in the middle of Sonoma County. Our 600 Sq ft Loft has all your home amenities. 5 minutes from J Winery and Rodney Strong among others. We have added your own private enclosed deck, so you can enjoy your space under the oaks. Compare to hotels with kitchens! $350.00+ IMPROVED WIFI as of 2/20/22!!!!

Dec 1 – 8

R2,658 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 148 reviews

Private upstairs guest suite with queen bed

Located in the heart of Sonoma County, enjoy a cozy, quiet neighborhood location that is walking distance to coffee shops, restaurants, shopping, kayaking, world-class mountain biking, and more! Only a short drive to downtown Santa Rosa, wine tasting, beer sipping, and redwood viewing.

Dec 22 – 29

R2,141 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windsor vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Windsor's top sights

Sonoma County Airport28 locals recommend

Windsor Town Green34 locals recommend

Riverfront Regional Park34 locals recommend

Airport Stadium 1221 locals recommend

Kendall-Jackson Wine Estate & Gardens46 locals recommend

KC's American Kitchen23 locals recommend

Other great vacation rentals in Windsor

Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 121 reviews

Vineyard Cozy Cottage & Hot Tub

Feb 14 – 21

R4,990 ZAR per night

Guest favorite

Guesthouse in Santa Rosa

4.94 out of 5 average rating, 664 reviews

Scenic Neighborhood Garden Cottage

Feb 8 – 15

R2,957 ZAR per night

Guest favorite

Home in Windsor

5.0 out of 5 average rating, 100 reviews

Large Home w/ HotTub 10 min to Downtown Healdsburg

Oct 7 – 14

R11,269 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 181 reviews

Wine Country Retreat

Jan 25 – Feb 1

R2,803 ZAR per night

Guest favorite

Apartment in Sebastopol

4.99 out of 5 average rating, 608 reviews

Amy's Local BNB - walk to town **and hot tub!**

Oct 11 – 18

R3,062 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.91 out of 5 average rating, 248 reviews

Peaceful Wine Country Retreat / PRIVATE ENTRANCE

Oct 14 – 21

R2,540 ZAR per night

Guest favorite

Guesthouse in Santa Rosa

4.96 out of 5 average rating, 169 reviews

KV garden Cottage.

Sep 29 – Oct 6

R2,542 ZAR per night

Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 301 reviews

Arbor View

Jul 13 – 20

R2,332 ZAR per night

Show all

Other great vacation rentals in Windsor

Guest favorite

Guest suite in Sebastopol

4.96 out of 5 average rating, 326 reviews

Quiet and peaceful Russian River Valley retreat

Sep 29 – Oct 6

R2,340 ZAR per night

Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 430 reviews

Dry Creek Valley Cottage

Nov 5 – 12

R3,790 ZAR per night

Guest favorite

Farm stay in Healdsburg

4.97 out of 5 average rating, 475 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Apr 21 – 28

R5,794 ZAR per night

Guest favorite

Guesthouse in Santa Rosa

4.91 out of 5 average rating, 656 reviews

The Hideaway-Private Garden Studio

Jun 24 – Jul 1

R2,845 ZAR per night

Guest favorite

Guest suite in Forestville

4.97 out of 5 average rating, 159 reviews

Forest Gem: peaceful retreat hot tub and firepit

Jun 4 – 11

R2,959 ZAR per night

Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 528 reviews

Healdsburg Garden House

Nov 18 – 25

R4,382 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.95 out of 5 average rating, 169 reviews

Cozy Private Guest Suite Centrally Located

Dec 30 – Jan 6

R3,186 ZAR per night

Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 118 reviews

Ranch Stay for 2

Nov 16 – 23

R2,520 ZAR per night

Show all

Quick stats about vacation rentals in Windsor

Total rentals
350 properties
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Rentals with a pool
230 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
250 properties are a good fit for families
Total number of reviews
12K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 160 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Windsor?
Four-legged friends are welcome in Windsor. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there Windsor vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 230 vacation homes with pools in Windsor, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Windsor?
Experience the best of Windsor with our condo 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.
Do apartment rentals in Windsor have a gym?
Absolutely! We offer over 20 apartment rentals with a gym in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Windsor have self check-in?
Absolutely! We offer over 60 apartment rentals with self check-in in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windsor have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Windsor have wifi?
Absolutely! We offer over 100 condo rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Windsor?
Windsor has more than 90 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Windsor?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 60 homes with self check-in, over 30 homes with wifi, over 60 homes with a bbq area, over 20 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Windsor vacation rentals

Top-rated vacation rentals in Windsor

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Other great vacation rentals in Windsor

Cottage in Windsor

Guesthouse in Santa Rosa

Home in Windsor

Guest suite in Santa Rosa

Apartment in Sebastopol

Guest suite in Santa Rosa

Guesthouse in Santa Rosa

Guesthouse in Sebastopol

Other great vacation rentals in Windsor

Guest suite in Sebastopol

Home in Healdsburg

Farm stay in Healdsburg

Guesthouse in Santa Rosa

Guest suite in Forestville

Home in Healdsburg

Guest suite in Santa Rosa

Home in Cazadero

Quick stats about vacation rentals in Windsor

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Windsor?

Are there pet-friendly vacation rentals in Windsor?

Are there Windsor vacation rentals on Airbnb with pools?

How much does it cost to stay in condo rentals in Windsor?

Do apartment rentals in Windsor have a gym?

Do apartment rentals in Windsor have self check-in?

Do house rentals in Windsor have a bbq area?

Do condo rentals in Windsor have wifi?

Are there family-friendly condo rentals in Windsor?

What are the most popular amenities for Apartment Rentals in Windsor?

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