
Holiday rentals in Windsor
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Top-rated holiday rentals in Windsor
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Country Studio Cottage Sanctuary
Cozy, quiet studio cottage nestled on 1/3 acre of trees and surrounded by seasonal creeks. Indoor gas fireplace and full kitchen & large spacious deck. In Sonoma Wine Country, 12 minutes to downtown gourmet restaurants, and organic coffee houses. Take gorgeous backroads to Bodega Bay and Sonoma Coast. Nestle into the warm glow of a gas fireplace or watch for deer and wildlife from the deck or living room. This is a perfect retreat space for one or two people; it is not appropriate for parties.

1 Bedroom Garden Apmt, Smart TV/AC, 85 Walk Score
Escape to our charming 1-bedroom courtyard apartment, thoughtfully designed for a cozy and comfortable stay. The kitchenette is fully equipped with a retro-style refrigerator, countertop oven with air fry capabilities, double hot plate, electric frying pan, and a versatile marble table/island. Relax in the inviting living area with a full-size sofa, desk, and Smart TV, or step through the sliding door to enjoy your morning coffee at the bistro table overlooking the shared courtyard garden. The s

Forest Cozy Home
My house in Forestville is a walk to the river (Steelhead County Beach), near endless wineries, canoe rentals, gorgeous Sonoma coast beaches, Santa Rosa airport, a bicycle trail through West County with bike rentals in downtown Forestville offering immediate access to the trail, and a very well-stocked little grocery store a 5-minute walk down the hill. Lovely back roads take you to Healdsburg to the north or Sebastopol to the south. My dog & I stay in a basement studio when guests are here.

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.

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.

Redwood Treehouse Retreat - Hot tub, fire pit
Welcome to our Redwood Treehouse Retreat, where cozy meets luxury in the heart of nature. Nestled in the ancient trees, this romantic escape offers privacy and indulgence. Relax in the hot tub, cozy up by the fire, recharge your EV, and explore. We’re centrally located: 5 min from Occidental, 10 min to Russian River/Monte Rio beach, 20 min to coast/Sebastopol, and 30 min to Healdsburg. A perfect base to discover all the wonders of this captivating region. Your dreamy, secluded getaway awaits.

Wikiup lookout retreat
We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

Gracianna Winery Vineyard Loft - Farm Stay
Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Winelight Vineyard Home With Spa
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.

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

Robin's Nest
Your second home is above our 2-car garage, a 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, a 10-minute drive to downtown Santa Rosa, 45-minute drive to the coast and little over an hour to San Francisco. We are centrally located to explore Sonoma and Napa County wineries, breweries and hiking trails. Permit #SVR23-170

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. The unit has short term permit form Santa Rosa SVR24-056.
Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Luxury Container Home w Infinity Pool + 360 Views

Rivermind , a Wine Country Retreat #1

Enchanting Russian River Retreat

Willowside House

Forest Gem: cozy getaway in the woods

WorldMark Windsor Two-Bedroom Condo - Sleeps 6!

Sunny View Loft

Wine and Golf Paradise in Windsor, CA (#1)
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $264 SGD | $261 SGD | $261 SGD | $260 SGD | $263 SGD | $289 SGD | $282 SGD | $267 SGD | $258 SGD | $284 SGD | $273 SGD | $271 SGD |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
Frequently Asked Questions
Where should I stay in Windsor?
Make yourself at home in Windsor by choosing from our most frequently booked neighborhoods. We have over 280 vacation rentals in East Windsor, and over 440 vacation rentals in Fulton.
Are there vacation rentals with a dedicated workspace in Windsor?
Yes! Work meets play with ease at over 140 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 40 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 260 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 serviced apartment rentals in Windsor?
Experience the best of Windsor with our serviced apartment rentals, starting at about $100 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 40 apartment rentals with a gym in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Windsor have self check-in?
Absolutely! We offer over 10 house 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 20 house rentals with a bbq area in Windsor. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Windsor have wifi?
Absolutely! We offer over 40 apartment 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 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Quick stats about holiday rentals in Windsor

Total holiday rentals
Explore 340 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 8,070 verified reviews to help you choose

Family-friendly holiday rentals
250 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
260 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
320 of Windsor holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Windsor rentals

4.9 Average rating
Windsor stays are highly rated by guests – averaging 4.9 out of 5!
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