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

Home in Windsor

5.0 out of 5 average rating, 101 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!

Sep 22 – 29

G$134,810 GYD per night

Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 251 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

Sep 24 – Oct 1

G$39,306 GYD per night

Guest favorite

Guest suite in Windsor

4.98 out of 5 average rating, 362 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.

Aug 23 – 30

G$26,341 GYD 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.

Jan 6 – 13

G$22,122 GYD per night

Guest favorite

Home in Windsor

4.96 out of 5 average rating, 381 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.

Sep 15 – 22

G$45,752 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 326 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 23 – 30

G$28,318 GYD per night

Superhost

Home in Healdsburg

4.81 out of 5 average rating, 426 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.

Jan 15 – 22

G$33,218 GYD per night

Guest favorite

Apartment in Santa Rosa

4.99 out of 5 average rating, 258 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.

Jul 3 – 10

G$24,723 GYD per night

Guest favorite

Cottage in Windsor

5.0 out of 5 average rating, 122 reviews

Vineyard Cozy Cottage & Hot Tub

Now booking monthly stays- let’s talk!!! Nestled in the Russian River Valley is where you will find Woolsey Road Cottage. Our spaciously designed 840 sf cottage is located on our 7 acre family owned property that is within 15 minutes to Santa Rosa, 15 minutes to the Russian River. We offer a beautiful cottage to rest and refresh close to multiple wineries, fantastic dining, great hiking and outdoor activities!

Oct 22 – 29

G$56,506 GYD per night

Guest favorite

Home in Windsor

4.95 out of 5 average rating, 138 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 19 – 26

G$74,040 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.9 out of 5 average rating, 677 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 25 – Jan 1

G$22,427 GYD per night

Guest favorite

Loft in Windsor

4.81 out of 5 average rating, 501 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 25 – Jan 1

G$28,811 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

Guest suite in Santa Rosa

4.97 out of 5 average rating, 152 reviews

Private upstairs guest suite with queen bed

Feb 27 – Mar 6

G$24,097 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 684 reviews

Sun Drenched Flat

Feb 23 – Mar 2

G$28,636 GYD per night

Guest favorite

Guest suite in Graton

4.95 out of 5 average rating, 265 reviews

The Flying Pig

Jul 18 – 25

G$21,501 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 182 reviews

Wine Country Retreat

Jan 25 – Feb 1

G$30,385 GYD per night

Guest favorite

Home in Windsor

4.99 out of 5 average rating, 101 reviews

Gorgeous Victorian in the HEART of Windsor

Jan 19 – 26

G$94,683 GYD per night

Guest favorite

Farm stay in Healdsburg

4.97 out of 5 average rating, 478 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Mar 7 – 14

G$62,801 GYD per night

Superhost

Guest suite in Santa Rosa

4.78 out of 5 average rating, 344 reviews

Dedicated Patio, Roku & Self Check-In

Sep 22 – 29

G$21,855 GYD per night

Guest favorite

Guest suite in Sebastopol

4.96 out of 5 average rating, 326 reviews

Quiet and peaceful Russian River Valley retreat

Jul 6 – 13

G$25,360 GYD per night

Show all

Other great vacation rentals in Windsor

Guest favorite

Apartment in Sebastopol

4.99 out of 5 average rating, 609 reviews

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

Sep 3 – 10

G$33,094 GYD per night

Superhost

Home in Santa Rosa

4.92 out of 5 average rating, 205 reviews

Charming 1-Bd Boho Flat Amid Wineries

Mar 25 – Apr 1

G$30,844 GYD per night

Guest favorite

Home in Healdsburg

4.93 out of 5 average rating, 529 reviews

Healdsburg Garden House

Mar 6 – 13

G$47,284 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 303 reviews

Arbor View

Jul 24 – 31

G$25,277 GYD per night

Guest favorite

Guest suite in Santa Rosa

4.84 out of 5 average rating, 232 reviews

Cozy private quiet in-law with garden entrance

Jun 23 – 30

G$20,141 GYD per night

Guest favorite

Guest suite in Forestville

4.97 out of 5 average rating, 161 reviews

Forest Gem: peaceful retreat hot tub and firepit

Oct 23 – 30

G$32,071 GYD per night

Guest favorite

Home in Cazadero

4.95 out of 5 average rating, 120 reviews

Ranch Stay for 2

Feb 10 – 17

G$27,312 GYD per night

Guest favorite

Guesthouse in Santa Rosa

4.91 out of 5 average rating, 658 reviews

The Hideaway-Private Garden Studio

Jun 13 – 20

G$30,840 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 serviced apartment rentals in Windsor have a gym?
Absolutely! We offer over 50 serviced apartment 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 40 condo 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 house rentals in Windsor?
Windsor has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Condo Rentals in Windsor?
Enhance your stay in our Condo Rentals with the most popular amenities: over 50 homes with a bbq area, over 100 homes with a gym, over 40 homes with self check-in, over 100 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

Apartments

Houses

Hotels

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Other great vacation rentals in Windsor

Guest suite in Santa Rosa

Guesthouse in Sebastopol

Guest suite in Graton

Guest suite in Santa Rosa

Home in Windsor

Farm stay in Healdsburg

Guest suite in Santa Rosa

Guest suite in Sebastopol

Other great vacation rentals in Windsor

Apartment in Sebastopol

Home in Santa Rosa

Home in Healdsburg

Guesthouse in Sebastopol

Guest suite in Santa Rosa

Guest suite in Forestville

Home in Cazadero

Guesthouse in Santa Rosa

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 serviced apartment rentals in Windsor have a gym?

Do condo 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 house rentals in Windsor?

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

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