Windsor vacation rentals

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Top-rated vacation rentals in Windsor

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Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 678 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.

Oct 15 – 22

G$28,693 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 249 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 7 – 14

G$39,385 GYD per night

Guest favorite

Home in Windsor

5.0 out of 5 average rating, 99 reviews

Large Home w/ HotTub 10 min to Downtown Healdsburg

Wine Country Living at its finest. Conveniently located just 10 minutes to Downtown Healdsburg, this spacious, elegant home features 4 bedrooms, 2.5 bathrooms and an open floor plan perfect for spending time with friends and family. Relax in the hot tub or around the fire pit in the backyard, play a game of ping pong or pool in the garage, or cozy up by the fireplace in the living room. This home is perfect for your Wine Country get-a-way. Only 1.6miles to the world famous Russian River Brewery!

Jul 15 – 22

G$142,283 GYD per night

Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 357 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.

Jul 24 – 31

G$25,107 GYD 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.

Jun 26 – Jul 3

G$94,690 GYD per night

Guest favorite

Home in Windsor

4.96 out of 5 average rating, 378 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.

Jun 26 – Jul 3

G$45,844 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.91 out of 5 average rating, 248 reviews

Peaceful Wine Country Retreat / PRIVATE ENTRANCE

Tax ID 2726N GUEST SUITE/PRIVATE ENTRANCE with Sitting Room, Large Private Bedroom & Bath. Includes a King size bed, Cable TV, Wi-Fi and Breakfast. Enjoy the beautiful view of the garden and rolling hills of Sonoma Valley’s Wine Country while relaxing in the fully stocked sitting room sipping on a glass of wine, tea, or coffee. In the evening, unwind on the patio that is just outside of the sitting room while sitting under the stars and majestic trees.

Dec 9 – 16

G$25,162 GYD 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

Jun 26 – Jul 3

G$28,375 GYD 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.

Dec 11 – 18

G$33,530 GYD per night

Superhost

Guest suite in Santa Rosa

4.78 out of 5 average rating, 343 reviews

Dedicated Patio, Roku & Self Check-In

Premium guest suite with private entrance, separate living room and dedicated outdoor patio area. Complete with complimentary popcorn, coffee, tea and water for your enjoyment. Located 2.4 miles to Down Town Santa Rosa & Russian River Brewing Company, half mile to groceries & restaurants, 7.4 miles to Sonoma County Airport and 2-5 miles to all major hospitals. Best for 2 guests due to size. Longer stays discounted. Permit Number: SVR21-197

Sep 3 – 10

G$21,899 GYD 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.

Jan 17 – 24

G$24,512 GYD per night

Guest favorite

Home in Windsor

4.95 out of 5 average rating, 136 reviews

Home near golf course w/Hot tub in Windsor

This gorgeous home is located just minutes from Russian River Brewery, the Santa Rosa airport and Dry Creek valley. It features 3 bedrooms and 2.5 bath, a hot tub, fire pit and large kitchen for you and your guests to enjoy! It also has a WFH space so you can make it a longer stay. The park in walking distance makes it perfect for the whole family to be entertained.

Sep 20 – 27

G$74,189 GYD 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

Guesthouse in Sebastopol

4.98 out of 5 average rating, 430 reviews

Modern Bungalow Downtown Sebastopol

Sep 2 – 9

G$24,090 GYD per night

Guest favorite

Guest suite in Graton

4.95 out of 5 average rating, 263 reviews

The Flying Pig

Sep 1 – 8

G$21,604 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.88 out of 5 average rating, 1038 reviews

Clean Comfy Cottage Downtown

Sep 23 – 30

G$20,520 GYD per night

Guest favorite

Home in Santa Rosa

4.88 out of 5 average rating, 233 reviews

Sunshine cottage

Dec 10 – 17

G$32,392 GYD 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

Feb 2 – 9

G$24,973 GYD per night

Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 120 reviews

Vineyard Cozy Cottage & Hot Tub

Nov 3 – 10

G$48,314 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 180 reviews

Wine Country Retreat

Jan 25 – Feb 1

G$30,446 GYD per night

Guest favorite

Guest suite in Sebastopol

4.96 out of 5 average rating, 324 reviews

Quiet and peaceful Russian River Valley retreat

Jul 2 – 9

G$25,411 GYD per night

Show all

Other great vacation rentals in Windsor

Guest favorite

Guesthouse in Santa Rosa

4.94 out of 5 average rating, 662 reviews

Scenic Neighborhood Garden Cottage

Sep 18 – 25

G$32,119 GYD per night

Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 526 reviews

Healdsburg Garden House

Mar 13 – 20

G$47,594 GYD per night

Superhost

Apartment in Windsor

4.88 out of 5 average rating, 147 reviews

Windsor 2 Bed/2 Bath Condo ~ Pool ~ Hot Tub ~ Gym

Sep 23 – 30

G$41,494 GYD per night

Guest favorite

Home in Windsor

4.93 out of 5 average rating, 147 reviews

Luxurious home and pool

Jul 23 – 30

G$118,841 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.96 out of 5 average rating, 169 reviews

KV garden Cottage.

Oct 3 – 10

G$27,703 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.97 out of 5 average rating, 224 reviews

Spring sale - Book Now & Save

Oct 2 – 9

G$37,003 GYD per night

Superhost

Villa in Healdsburg

4.94 out of 5 average rating, 112 reviews

Hilltop Vista Villa

Mar 10 – 17

G$94,792 GYD per night

Guest favorite

Home in Healdsburg

4.96 out of 5 average rating, 430 reviews

Dry Creek Valley Cottage

Mar 1 – 8

G$41,161 GYD 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 condo rentals in Windsor have a gym?
Absolutely! We offer over 100 condo rentals with a gym in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Windsor have self check-in?
Absolutely! We offer over 30 condo rentals with self check-in in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Windsor have a bbq area?
Absolutely! We offer over 60 apartment 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 Serviced Apartment Rentals in Windsor?
Enhance your stay in our Serviced Apartment Rentals with the most popular amenities: over 50 homes with a gym, over 50 homes with wifi, 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

Houses

Apartments

Hotels

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Other great vacation rentals in Windsor

Guesthouse in Sebastopol

Guest suite in Graton

Guesthouse in Santa Rosa

Home in Santa Rosa

Guest suite in Santa Rosa

Cottage in Windsor

Guest suite in Santa Rosa

Guest suite in Sebastopol

Other great vacation rentals in Windsor

Guesthouse in Santa Rosa

Home in Healdsburg

Apartment in Windsor

Home in Windsor

Guesthouse in Santa Rosa

Guesthouse in Santa Rosa

Villa in Healdsburg

Home in Healdsburg

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 condo rentals in Windsor have a gym?

Do condo rentals in Windsor have self check-in?

Do apartment 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 Serviced Apartment Rentals in Windsor?

Destinations to explore